On the first Monday in May, the upper echelons of the fashion industry gather on the Upper East Side for the most opulent display of style, taste and creative excellence; more commonly known as the Met Gala.

For the uninitiated, the annual charity ball has been hosted for three-quarters of a century and raises funds for the Metropolitan Museum of Art's Costume Institute. With an exclusive guest list that gathers aristocrats, designers, actors, musicians, athletes, business tycoons and titans in their respective industries, the show-stopping night has come to be known as the crème de la crème of the sartorial calendar.

The actual proceedings of the event are an enigma thanks to a strict no-phones policy—save for star-studded selfies captured in the ladies’ room—making it also one of the most secretive events across the East Coast.

But of course, the real standout of the evening is the array of looks that grace the red carpet. Serving as a proverbial runway, the granite front steps are elevated beyond disbelief, serving both a literal and figurative platform for the haute couture creations that exceed all expectations.

From Gigi Hadid’s bespoke Thom Browne gown that made history for taking over 13,500 hours to construct to Dua Lipa wearing a completely beguiling 100-carat Tiffany & Co. necklace that was reportedly worth over $100 million USD, these ensembles aren’t for the faint of heart.

And with the annual Met Gala just around the corner, we felt it pertinent to revisit the best Met Gala dresses of all time. Blood racing, heart pumping, jaw-dropping and gasp-inducing, consider this the ultimate guide to the most memorable looks of all time.

The 13 Best Met Gala Dresses of All Time

1. Rihanna

Style Notes: With the theme as expansive and loaded with historical connotations as “Heavenly Bodies: Fashion and the Catholic Imagination,” it was only fitting that Rihanna take not only the most subversive route, but also the most straightforward.

Quite literally taking the fashion set to church, the multi-hyphenate musician and makeup mogul opted for a custom silver Maison Margiela cape-and-dress concoction designed by John Galliano. The pièce de résistance, however, was her homage to papal regalia in the form of her Stephen Jones headpiece. Hers is one conclave we’d gladly join.

2. Princess Diana

Style Notes: Six months after Princess Diana enshrined her fashion legacy by turning up to the Serpentine Gallery Summer Party wearing the inimitable revenge dress designed by Christina Stambolian, the late Lady Spencer made a discreet public outing to deliver another iconic ensemble for the ages.

Blending in with the Manhattan evening, she arrived at the soiree in an understated midnight blue slip dress designed by John Galliano for Christian Dior. (Just one of the British enfant terrible’s many features on this list.) Her one and only appearance at the event eventually came to define her sartorial shift following her separation from King Charles III; elegant, unburdened and an expression of her true sense of self.

3. Mary-Kate and Ashley Olsen

Style Notes: without an appearance from the perennially mysterious Olsen Twins. Mary Kate and Ashley have been fixtures at the soirée since they were 18 years old, making the event a true home-away-from-home for the secretive duo. However, it was at the 2017 iteration, which was themed “Rei Kawakubo/Comme des Garçons”, where The Row designers made their biggest impact.

Returning to their bohemian roots, the duo arrived in truly antique lace slip dresses that were reportedly over a century old. Dripping in pendant necklaces, fur-trimmed jackets and chunky accessories, the looks also honoured the Japanese designer’s autumn/winter 2005 collection “Broken Brides”, which was a subtle full-circle moment, given it also acknowledged the year they first started attending.

4. Zendaya

Style Notes: You can rest assured that whenever Zendaya has confirmed her RSVP, a sartorial feast is guaranteed. As one of the pioneers of method dressing, the 29-year-old takes her job as a guest incredibly seriously. However, when it came to her co-chairing the event in 2024, she exceeded all expectations.

Not only did she both open and close the red carpet with two separate but incredibly visionary looks, she delivered the most hauntingly beautiful interpretation of the theme “Sleeping Beauties: Reawakening Fashion”. With the dress code being "The Garden of Time," which was inspired by J.G. Ballard's 1962 short story exploring themes of beauty, decay, and the fleeting nature of time, she wore a custom gown by John Galliano for Maison Margiela that embodied the ephemeral and elegant source material. Quite euphoric.

5. Kate Moss

Style Notes: Another iconic co-chair came in the form of Kate Moss. Attending the 2009 iteration, which adhered to the theme “The Model as Muse”, she proved the power that supermodels wield as the ultimate shapeshifter. A true incarnation of Marc Jacobs' vision for the evening, she ditched her Camden-core leather jackets, skinny jeans and knee-high boots for a gold lame mini dress and matching Elizabeth Taylor-inspired turban.

6. Zoë Kravtiz

Style Notes: One of the symbols for Anthony Vaccarello’s sensually sophisticated visions for Saint Laurent, Zoë Kravitz was truly firing on all cylinders when she arrived at the 2021 Met Gala. Dressing to the theme “In America: A Lexicon of Fashion”, the actor-turned-director’s phenomenally risqué wore what could only be described as a netted dress made from dazzling crystals that made the shape of itty-bitty YSL monograms. Because who needs a slip dress when you’re dripping in diamantes?

7. Lady Gaga

Style Notes: Why have one look when you can have four? That was the thesis question that Lady Gaga designed her 2019 Met Gala ensemble around, landing on a captivating Brandon Maxwell look that was part performance art, part moving installation and completely camp.

Beginning with a magenta overcoat that featured an elongated train and accompanied by five dancers, she later slipped into a gown before changing into a Madonna-esque column dress, before closing out her epic entrance in a sequin-encrusted black bralette, panties, fishnet tights and platform booties.

8. Lily-Rose Depp

Style Notes: As someone who was appointed as one of Karl Lagerfeld’s “choupettes” as a teenager, it should come as no surprise that Lily-Rose Depp has almost unlimited access to Chanel’s archives for her public appearances.

At the 2019 Met Gala, The Idol star embraced the French maison’s most vampy silhouettes in a little black dress adorned with gold chains and gilded camellias. The piece was also first worn by Christy Turlington on the luxuriate’s spring/summer 1992 runway and later featured on Penelope Cruz in Pedro Almodóvar’s 2009 romantic thriller Broken Embraces.

9. Naomi Campbell

Style Notes: From walking the runway alongside her fellow “supers” to George Michael’s “Freedom” for Versace’s autumn/winter 1991 show to wearing the Italian designer’s iconic chainmail butterfly dress to an event alongside Kate Moss in 1999, Naomi Campbell has had no shortage of iconic Versace moments in her lifetime. Of course, the most sentimental moment came when she attended the 1995 Met Gala—the first hosted by Anna Wintour—alongside the brand’s founder, Gianni.

10. Tyla

Style Notes: It’s quite a feat to make the Met Gala best dressed list on your first time attending. But that’s exactly what South African pop sensation Tyla did for the 2024 event. In the spirit of surrealism and trompe l'oeil, the singer arrived in a Balmain dress that evoked the sands of time.

The gown was a custom fit to her figure and ended up being so tight that she needed to be carried up the steps by a security guard. Made from a plaster moulding that combined mica and mirror powder, the look was a true standout and firmly established her place in fashion’s elite circles.

11. Kendall Jenner

Style Notes: Though she might be known for her signature stealth wealth way of dressing, Kendall Jenner delivered her most high-octane look when attending the 2019 Met Gala in custom Versace. Wearing Marty Supreme orange and a feathered gown that left a trail of plumage, the look has become incredibly iconic over the years for the way the showgirl-esque silhouette completely transformed the model turned tequila maven. Later that year, for her Halloween-themed birthday party, the waiters were dressed up in this exact costume, proving just how camp the look actually was.

12. Kim Kardashian

Style Notes: Of course, it wouldn’t be a guide to the most iconic Met Gala dresses if it didn’t include this Kim Kardashian look on the list. Love it or hate it, this infamous Riccardo Tisci for Givenchy design helped segue the reality star and aspiring lawyer into a new stratosphere of fame.

Whilst many were vicious in their lamenting over her attendance at the event in the first place, the majority were brutal in tearing down the dress itself. Earning comparisons to Robin Williams in Mrs Doubtfire and even the couches owned by grandmothers, it's safe to say that Skims founder herself had the last laugh, given how iconic this look has become in its own right.

13. Anne Hathaway

Style Notes: Bearing resemblance to both an Oscar statuette and Star Wars character C3PO, Anne Hathaway’s Ralph Lauren dress from the 2015 Met Gala just proves how ahead of the fashion curve she is. This is a fact we might all recognise now, but it wasn’t the case over a decade ago. But as her fictional grandmother in The Princess Diaries, played by the incredibly Dame Julie Andrews, said, a queen is never late, everyone else is simply early.

What Is The Theme of the 2026 Met Gala?

As announced by VOGUE, the theme of the 2026 Met Gala is "Costume Art". As always, the theme is derived from the Costume Institute's spring exhibition. According to the centre's head curator, Andrew Bolton, the theme addresses “the centrality of the dressed body in the museum’s vast collection".

The museum reports that the exhibition will "pair garments with artworks to reveal the inherent relationship between clothing and the body". It continues, "from the formal to the conceptual, the aesthetic to the political, the individual to the universal, the illustrative to the symbolic, and the playful to the profound, these pairings are organised into a series of thematic body types that reflect their pervasiveness and endurance through time and cultures."

The exhibition is sponsored by tech billionaire Jeff Bezos and his wife, Lauren Sanchez Bezos, Saint Laurent and Condé Nast.

What is the Dress Code for the 2026 Met Gala?

Accompanying the theme, guests are invited to adhere to a compulsory dress code that further elucidates the crux of the exhibition. Keeping things incredibly simple for the 2026 event, the dress code is "Fashion is Art". This can be translated however the guest sees fit and can run the gamut from gowns that literally transpose famous works onto fabric to dresses that embrace the Métiers d'Art (or arts and crafts) that underscores any ensemble.

When is the 2026 Met Gala?

Like clockwork, the 2026 Met Gala is set for Monday, May 4, 2026. As the event is held in New York City, those of us here in the United Kingdom should expect to see looks from the red carpet begin to trickle in during the early hours of Tuesday, May 5, 2026. Gird your loins!

It was the best of times (sleek minimalism, distinct sub-cultures and Karl Lagerfeld at Chanel), it was the worst of times (gaudy trainers, ultra-baggy denim and a lack of online stores). But either way you cut it, the ‘90s were a time of memorable fashion, at least that’s the case for iconic ‘90s winter outfits.

From the reign of supermodels on the runway to the rise of legendary film starlets gaining cultural cache both on and off the red carpet, this decade delivered so many moments to take stock of. Yet, in my personal and professional opinion, there’s no better season for these tropes to excel than in cold weather.

Those with taste always turn to the past for sartorial inspiration. It’s why you’ll always see Alexa Chung channel her inner Courtney Love in a minidress and leopard-print coat, or Lila Moss take cues from her mother’s archive in a silky slip, fur-trimmed jacket or cigarette trousers. Whilst there’s no shortage of looks to mine if you’re ever in need of exemplary displays of style, I’ve always found that cooler settings are where these ensembles shine.

Prolific dressers of the time period delivered a masterclass in how to combat the elements with aplomb, mixing fuzzy coats with thermal layers to showcase how keeping frostbite at bay can actually be a chic affair.

There’s, of course, Carolyn Basette-Kennedy roaming the streets of New York in vintage Prada and Calvin Klein. Or, the likes of Cindy Crawford, who made every outing all the more sophisticated in her commitment to pared-back but well-edited wardrobe staples. Even, on the other side of the country in Los Angeles, someone like Winona Ryder, who proved that tailoring never goes astray.

The best of all, however, is simply how timeless these looks are. Though nearly 30 years have passed since these iconic ‘90s winter outfits were worn, they haven’t been subjected to the way the passing of time can age things. Classic and contemporary in equal measures, these are silhouettes that will only increase in relevance the further that we get away from them. (You only need to see the fervour that surrounds Tom Ford’s collections for Gucci for evidence of this fact.)

But to me, these iconic ‘90s winter looks serve more as an antidote to the vicious hyper-accelerated trend cycle or constant regurgitation of niche aesthetics than anything else. Yes, triangle scarves and textured hats might be trending now, but to truly wear them well, you must look back at when these pieces originated. In fact, I’d even wager that these items are only relevant now because of the elegant It girls who wore them first.

At least, that’s the mood I’m channelling, with the impactful looks I’ve chronicled ahead, ones I’ve pegged to replicate over the next few months. So, without further ado, keep scrolling through for the 11 most iconic ‘90s winter outfits that will certainly influence your own, as they have mine.

But before we begin, test your knowledge of the most iconic '90s winter outfits with our short quiz, below.

The 11 Most Iconic '90s Winter Outfits

1. Gwyneth Paltrow

Style Notes: Gwyneth Paltrow has always been a beacon of discerning minimalism. Whilst her looks today lean more clean-cut with a coastal, Californian edge, the actress and wellness maven's sense of dress back in the '90s was fitting with the grit and industrial slant of New York, where she spent her teenage years. From charcoal-coloured sets to animal print coats, her wardrobe is a case for polish with an attitude.

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2. Carolyn Basette-Kennedy

Style Notes: Known mononymously as CBK, the late Calvin Klein publicist is a perennial enigma. She was exceptionally private, especially as her marriage to political scion John F. Kennedy Jr. brought her closer to the limelight, meaning the only glimpses at her personal life were through the clothes she armoured herself in. Thankfully, these were always equally remarkable, including an arsenal of Manolo Blahnik, Jean Paul Gaultier and Cartier.

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3. Winona Ryer

Style Notes: From Heathers to Hawkins, Winona Ryder has always been something of fashion's enfant terrible. As one of the original scream queens, the actress has never shied away from a darker sensibility made popular today by Gabriette or Jenna Ortega. Slightly gothic, slightly grungy, but always fitted and austere, her looks are the definition of haunting glamour.

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4. Cindy Crawford

Style Notes: Olivia Rodrigo might have herself pegged as this century's All-American girl, but if we were to look back to the '90s, it's Cindy Crawford who would've been crowned this title. Having grown up on the outskirts of Chicago, Crawford's proximity to fashion's elite in style capitals like Paris and Milan never strayed her from her inimitable penchant for effortless, breezy style. Her winter outfits demonstrate that considered cuts and thoughtful shapes will never falter.

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5. Sarah Jessica Parker

Style Notes: Whether on screen as Carrie Bradshaw or off-duty in her own right, Sarah Jessica Parker has always held her own. This textured coat is the exact thing you'd find in so many modern savant's wardrobes, including a up-cycled Conner Ives version, a leopard-print style from Queens of Archive and a rebelliously fringed iteration from East London-based brand Jakke.

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6. Jennifer Aniston

Style Notes: If you were to stroll through Primrose Hill on a Saturday morning or any Hackney cocktail bar on a Saturday evening, you'll be sure to find someone wearing something similar to what Jennifer Aniston wore here to the second annual Women in Film event in 1999. From the shearling-effect coat to the straight-leg trousers and square-toe boots, this is an outfit that's as easy to copy as it is to shop.

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7. Julia Roberts

Style Notes: Winter fashion isn't as fickle as other seasons tend to be. But, if there is one piece that will always endure, it's the grey coat. Here, whilst filming something in New York in 1999, Julia Roberts shows exactly why. Pairing it with her megawatt smile, chunky loafers and pleated trousers, the iconic look demonstrates that when it comes to battling cold weather, sometimes your coat can be your entire outfit.

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8. Halle Berry

Style Notes: A velvet shirt? Check. A boxy blazer? Tick. Leather boots that graze the knee? Yes, indeed. Halle Berry's '90s winter outfit isn't a far cry from something you'd find in suburbs like Greenwich Village or Le Marais today. Take notes from the Catwoman star and opt for sumptuous materials and evening-appropriate shapes.

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9. Princess Diana

Style Notes: Though Princess Diana famously spent the season in exclusive alpine villages throughout Austria, she still made her stomping ground of London a place to parade her iconic winter outfits. Here, she injects her frosty white base layer with a hint of royal prep as she heads to a day of shopping in Knightsbridge.

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10. Sofia Coppola

Style Notes: Before she was the auteur of soft and saccharine femininity with films like The Virgin Suicides and Marie Antoinette, Sofia Coppola was making a name for herself in the underground scenes with a short-lived television series she co-hosted with fellow Hollywood nepo baby Zoe Cassavetes called Hi Octane. This picture was taken of her during the show's run in 1994, epitomising her candid and dreamlike approach to fashion that would come to define her later work.

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11. Courteney Cox

Style Notes: Slouchy and carefree aren't the traits we attribute with Courteney Cox's iconic role as Monica Geller in Friends. But, it's this uncomplicated approach to style that's come to define her iconic off-duty style. Breathable and light, this outfit can be dressed up and down for the climate, just add a lightweight turtleneck and a leisurely V-neck jumper.

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When I think of iconic ‘90s outfits, my mind instantly wanders to a few pivotal points during the decade. There's the '90s fashion cemented in popular culture, like Carrie Bradshaw’s eminently eclectic designer wardrobing on Sex and the City or Monica Geller’s considerate casualness in Friends.

Then there are the runway moments, including but not limited to Versace’s Freedom! Climax in 1991, whereby Linda Evangelista, Christy Turlington, Cindy Crawford and Naomi Campbell closed the show dressed in monochromatic shift mini dresses and mouthing the lyrics of George Michael’s anthem, Marc Jacobs’ grunge collection for Perry Ellis in 1994 and Mugler’s haute couture cyborg suit from 1995.

On stage, there was no shortage of spotlight-stealing ensembles, including Madonna’s Jean Paul Gaultier cone bra, which she wore during her 1990 Blonde Ambition world tour, or TLC’s genre-defying and gender-bending matching streetwear.

The red carpet forays are equally momentous, like Elizabeth Hurley’s slinky safety pin dress from the premiere of Four Weddings and a Funeral or the chartreuse chinoiserie Dior by John Galliano gown Nicole Kidman wore to the 69th annual Academy Awards in 1997.

However, as someone whose credentials to comment on the matter include being born six months before the turn of the 21st century in the June of 1999, the most iconic ‘90s outfits aren’t the ones you’ll find on screen or played up for an audience. Instead, the decade’s biggest contributions come in a more insouciant approach, like model off-duty sightings or the days celebrities went to events without being dressed by a stylist.

To me, the most iconic ‘90s outfits stand as a time capsule. They reflect what personal style looked like without the influence of niche aesthetics, self-surveilling social media or the ability to commodify your outfit of the day through brand deals and paparazzi shots. As Cindy Crawford said during an interview meditating on her life in looks, “No one put [my outfit] together other than just what I grabbed.”

From Princess Diana’s revenge dress, Oscar appearances no one saw coming and Posh and Becks's most recognisable look, uncover the 16 most iconic ‘90s outfits of all time, ahead.

The 16 Most Iconic '90s Outfits

1. Kate Moss's Slip Dress

Style Notes: Cherubic and fresh from Croydon, Kate Moss began the decade by gracing the cover of The Face's July 1990 issue. She might've been only 16 at the time, but only three years later, she would go on to wear a look that defined the '90s. Indeed, her humble slip dress was slinky, lingerie-inspired and, according to an interview she gave in 2023, unknowingly "see-through".

"The pictures came out the next day in the newspaper, and it was the flash that made it look 'naked'," Moss said of the Liza Bruce piece, which she wore to the Elite Model Agency party for the Look of the Year in 1993.

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2. Victoria Beckham's Chainmail Halterneck Top

Style Notes: A power couple if there ever was one, David and Victoria Beckham's '90s fashion gave way to the mode of coordinating style to strengthen one's public persona. On their own, the Spice Girl and the English footballer had flair in spades. But it was when they were spotted out together wearing similar outfits that piqued interest the most. This look, which was worn to an event in London in 1999, is one of the former pop star turned fashion designer's more demure. Still, the combination of the chintzy halterneck top and animal-print shoe remains one of the best in her oeuvre.

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3. Princess Diana's Revenge Dress

Style Notes: Princess Diana's revenge dress is, in my opinion, the most iconic '90s outfit. Not only is this gown a symbol of her use of fashion as a form of rebellion and silent strength, but the acme of how the late Lady Spencer approached her role in the royal family. For the uninitiated, the former Princess of Wales wore this little black dress to a gala in Hyde Park's Serpentine Gallery on the same night the now King Charles III confessed to committing adultery during their marriage during a televised interview. So, what do you wear when your ex-husband and heir to the throne reveals to have cheated on you to the public? A fitted and strapless Christina Stambolian design with a floaty chiffon train, of course.

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4. Carolyn Bessette-Kennedy's Street Style

Style Notes: Carolyn Bessette-Kennedy has come back into the zeitgeist with the impending release and current production of Ryan Murphy's upcoming limited series, American Love Story. The furore around the historically inaccurate costuming proves exactly why CBK's fashion legacy remains perennially inimitable. Her unwavering commitment to minimalism set a precedent that Manhattan darlings still follow today. Of course, as a publicist for Calvin Klein, her wardrobe was always functional and apt for corporate settings, meaning workwear staples like white button-down shirts and midi skirts were always present, yet nonetheless designer, given her penchant for Prada, Miu Miu and Yohji Yamamoto.

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5. Jennifer Lopez's Waistcoat Dress

Style Notes: Her hit single "Jenny From The Block" mightn't even hit the airwaves by the time this picture was taken, but Jennifer Lopez's '90s fashion era is proof that the New Yorker has always been a force to contend with. A smidge more mindful than the glamorous outfits that succeeded the decade in the early 2000s, this waistcoat dress epitomises her girl next door origins.

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6. Mariah Carey's MTV VMAs Two-Piece

Style Notes: Taking a page from Princess Diana's book, Mariah Carey put her own spin on revenge dressing when she attended the 1997 MTV Video Music Awards wearing a sultry two-piece set after announcing her split from then-husband Tommy Mottola. The simplicity of the co-ord really demonstrates why minimalism was so pervasive. (See: clean lines and unfussy elegance.)

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7. Gwyneth Paltrow's Tom Ford for Gucci Suit

Style Notes: Gwyneth Paltrow might've helped pioneer terms like "conscious uncoupling" and a well-rounded lifestyle that involves dry brushing, infrared saunas, and yoni eggs, but before she was the Goop juggernaut we know her to be, she was an actress with a street style that focused on refined ease. This came to the forefront in 1996, when Paltrow wore a burgundy Gucci suit designed by Tom Ford to the MTV VMAs. The suit was fresh of the runway, having made its debut in the autumn/winter season that year, showcasing her know-how and ability to make effortless and well-tailored pieces covetable as far back as 30 years ago. In 2022, Paltrow rewore this look for Gucci's Hollywood-inspired Love Parade collection, wearing a recreation designed by Alessandro Michele for the Florentine maison's Aria collection a year earlier.

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8. Céline Dion's Backwards John Galliano Suit

Style Notes: Céline Dion's recent documentary might have helped thrust the French-Canadian diva's style philosophy into the spotlight. (If you haven't seen, she confessed to owning over 10,000 pairs of shoes and will buy any style she likes regardless of size: "I walk the shoe, the shoe don't walk me".) Even all the way back in 1999 was she living by her own rules, like the time she attend the 71st Academy Awards wearing a John Galliano for Dior suit backwards.

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9. Iman's Floral Dress

Style Notes: While Posh and Becks catapulted their stardom through matching outfits, the opposite could be said for David Bowie and legendary supermodel Iman. He was the androgynous rockstar, and she was the fashion vixen, which is really apparent in this outing to the 1999 MTV VMAs. While the Ziggy Stardust singer's outfit looks like something you'd find at The Row, Iman is a vision in this floral, body-conscious dress.

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10. Julia Roberts's Armani Men's Suit

Style Notes: From the underarm hair-exposing red sequin Vivienne Tam dress that she wore to the premiere of Notting Hill to her infamous pre and post-makeover Pretty Woman costumes, Julia Roberts is synonymous with iconic '90s outfits. However, the one that feels the most timeless is this Giorgio Armani men's suit that she wore to the 1990 Golden Globes. Taking home the prestigious award for Best Supporting Actress for her performance in Steel Magnolias, she did so wearing the tailored two-piece that she picked up earlier on Rodeo Drive. (Very Vivian Ward of her!) Remaining on moodboards ever since, Ayo Edebiri recreated the look in a Loewe version for the 2025 ceremony.

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11. Winona Ryder's Casual Film Premiere Look

Style Notes: As a formidable child star who broke out into the mainstream during the '80s Brat Pack era, by the time the '90s rolled around, Winona Ryder was a seasoned professional in Hollywood spheres. This look from 1991 is one of her most unintentionally punk and indicative of how different the industry was back then. With this picture taken of the star on her way to a film premiere, her simple jeans and a nice top formula feels fresh, unpretentious and makes me nostalgic for a time when turning a look wasn't of paramount importance.

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12. Halle Berry's Airport Outfit

Style Notes: Take it from Halle Berry; jeans and a leather jacket are an undeniable '90s silhouette. This is a more relaxed take compared to Winona's, which makes it the perfect model for the iconic '90s airport outfits that were so prevalent during this time.

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13. Jennifer Aniston's New York Off-Duty Outfit

Style Notes: Jennifer Aniston might've introduced herself to the world via her bubbly, preppy and somewhat spoiled Friends character, Rachel Green. And while her costuming will always be relevant, her off-camera looks are equally enticing, too. Here, while shooting a film in 1997, she puts a '90s fashion twist on layering by teaming a strappy mini dress over a white t-shirt before tying it all together with a tied-up longsleeve, woven bag, backwards cap and a micro sunglasses.

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14. Pamela Anderson's Vivienne Westwood Corset

Style Notes: When it comes to iconic '90s outfits, Pamela Anderson has certainly made a few entrances into the canon. From her bombshell all-leather looks during her Barb Wire press tour to the red swimsuit of her Baywatch era, and even the fuzzy pink hat she wore to the 1999 MTV VMAs, Anderson has done her part in etching this decade's fashion into the annals of history. Personally, I adore this more whimsical moment which took place in Australia in 1994. Wearing a Vivienne Westwood corset dress, the fairytale feeling of the garment contradicts her more vampy persona, making it an inspired choice on her part. Plus, the bubble skirt and brocade detailing remind me of something you'd find at the likes of Turner Vintage or Annie's Ibiza. If Pamela shopped at Portobello Road...

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15. Chloë Sevigny's Tiger Print Stockings

Style Notes: One of the original it girls, Chloë Sevigny is the patron saint of iconic '90s outfits. Taken just after her debut in Larry Clarke's Kids and appearance in Miu Miu's spring/summer 1999 runway, this outfit captures Sevigny in her element, complete with a hodgepodge of high-fashion paraphernalia like tiger-print stockings and a rosette to adorn her velvet one-shoulder dress.

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16. Naomi Campbell's Vivienne Westwood Platforms

Style Notes: This edit wouldn't be complete without an appearance from Naomi Campbell. As her recent solo exhibition at London's V&A Museum made apparent, the supermodel's wardrobe choices are nothing short of iconic, but I personally adore this Vivienne Westwood outfit that she wore to the Designer of the Year Awards at the Natural History Museum during London Fashion Week in 1993. Her choosing to don these Yves Klein blue thigh-high stockings and platform shoes came only months after she took a tumble on the designer's runway earlier that year. Her powerful reclamation of this moment is nothing short of legendary and proves why Campbell is so revered, respected and renowned as a fashion force.

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I'm definitely biased, but I think tennis is the most stylish sport. Top-ranked players wear Miu Miu skirts and Rolex watches, and spectators are often dressed like they've walked out of a Ralph Lauren ad. This is true for all four of the Grand Slam tournaments each year, but nowhere is the convergence of fashion and tennis more apparent than at Wimbledon.

On court, players are required to adhere to the tournament's strict all-white dress code, but they still find ways to make fashion statements. In 2025, for instance, Coco Gauff wore an intricate white dress by New Balance. "It's incredible the embroidery work they designed for that dress," says Sunita Kumar Nair, author of the new book Ace: The Times & Style of Tennis. "It's kind of like British punk and Vivienne Westwood and rock and roll and all the things that Coco likes. It's so detailed. It's like couture."

"I think there is a really strong argument that performance design is very close to couture," Kumar Nair continues. "The fabrics are tried and tested, and it's a really big journey for the athlete. The outfits can take a year to design." My favorite fashion moment included in Ace is Roger Federer's cream-colored cable-knit cardigan with gold trim, which he wore to Wimbledon in 2008. By the time he removed the sweater to hit his first serve, he had already solidified his place in tennis fashion history.

"There's a beautiful relationship between fashion designers and sports stars now, and it's just getting bigger and bigger," Kumar Nair tells Who What Wear. "I was just reading that Jack Draper has signed a $5 million deal with Vuori, and Naomi Osaka was just at the Met Gala. I think there is so much that's going to happen with the sports world and, in particular, tennis because of the kind of money that it can engender."

As we wait to see exactly how fashion and tennis will converge this year at Wimbledon, which kicks off on June 29, scroll down to revisit the most stylish outfits on and off Centre Court, from Princess Diana and Meghan Markle to Serena Williams and Stan Smith.

1. Polka Dots

In 1987, Princess Diana sat courtside in the Royal Box wearing red-and-white polka dots.

Wearing polka-dotted Alessandra Rich, Kate Middleton presented the Gentlemen's Singles Trophy to Novak Djokovic in 2022.

Then pregnant with her first child, Margot Robbie wore polka-dotted Alaïa to the championships in 2024.

Dairy Boy founder Paige Lorenze wore a polka-dot Self-Portrait dress to cheer on Tommy Paul at Wimbledon in 2024.

Polka dots are nothing new around the Wimbledon grounds. British actress Aleta Morrison wore the classic print to the event in 1959.

Anna Wintour, ever the tennis fan, attended the tournament in 2023 wearing a polka-dot dress by Balenciaga.

2. Butter-Yellow Suiting

Princess Diana wore a pastel-yellow skirt suit to the championships in 1995.

One takeaway from looking through decades of Wimbledon outfits: Butter yellow is a very popular color to wear to the tournament. Here, Emma Corrin shows how it's done.

Poppy Delevingne wore butter yellow to the men's finals in 2022.

3. Varsity Sweaters

Name a more iconic cardigan—I'll wait. Federer's 2008 sweater will go down in fashion history.

Williams wore a varsity cardigan during warm-ups in 2011. She shed the extra layer once her matches started, revealing a white dress underneath.

Tim Henman—the former number one British tennis player for whom Henman Hill is named—was pictured strolling around Wimbledon between matches in a varsity sweater in 1994.

Six years before Adidas named its iconic sneakers after him, Smith hoisted the Gentlemen's Singles Trophy in 1972 wearing a varsity sweater.

Arsenal soccer star Myles Lewis-Skelly, pictured here in 2025, is also a fan of the trend.

Frank Hunter and Algernon Kingscote competed against each other at Wimbledon in 1927. Varsity sweaters have never gone out of style in the nearly 100 intervening years.

4. Striped Button-Down Shirts With and Without Ties

In 2024, Zendaya continued to play up the tennis theme of her movie Challengers by attending the women's final.

My favorite Meghan Markle outfit ever? Her 2018 Wimbledon look.

French actress Joséphine Japy wore a chic Ralph Lauren outfit to the event in 2025.

In 2019, Tessa Thompson wore a stylishly slouchy Polo Ralph Lauren look.

David Beckham looked posh (get it?) attending the event in 2021.

5. Gingham

Olivia Rodrigo attended a Centre Court match in 2025 wearing a red gingham Ralph Lauren dress.

Jessica Plummer was also on board with the gingham trend in 2025.

Lady Amelia Windsor wore a cute gingham baby-doll dress to Wimbledon in 2025.

Catherine, Princess of Wales and Princess Diana are both revered as royal fashion icons, but I’ve never considered their personal styles to be particularly alike. Diana’s wardrobe was rooted in the hallmarks of '80s fashion, gradually transitioning into the sleek minimalism that defined her '90s looks. In contrast, Kate Middleton has long favoured a more restrained and consistent aesthetic; think tailored dresses, jewel-toned hues and classic accessories—a style formula that has remained largely unchanged since her royal debut.

That’s why I did a double take when I saw Middleton step out in an outfit that could have been lifted directly from Princess Diana’s archive. Attending a service in central London to mark the 80th anniversary of VE Day, Middleton wore a white, midi-length polka-dot dress by Alessandra Rich, with a high neckline, voluminous sleeves and a softly cinched waist. The silhouette and print are so reminiscent of Diana’s iconic style, the dress sparked instant déjà vu.

Meanwhile, the former princess once wore a strikingly similar white polka-dot ensemble to Epsom Races circa 1986; a structured two-piece with a nipped-in waist, peplum skirt and bold shoulders, complete with uniform dots. The resemblance was uncanny.

Enduringly elegant, this timeless print feels as relevant today as it did in '86. Accessorising hers with DeMellier's The Midi Montreal bag (£435), Middleton injected a distinctly modern twist into her look, completing it with nude pointed-toe heels, pearl drop earrings and a black headpiece.

A classic design with plenty of mileage, read on to discover the best white polka-dot dresses to shop now.

SHOP WHITE POLKA-DOT DRESSES:

While browsing through H&M's new arrivals for a story—yes, it's is part of my job—I saw a sporty sweater that looked incredibly familiar. Then it hit me: none other than Kate Middleton has worn a similar version before. And upon further digging, I found a photo of the late Princess Diana in the very same trend, too. Is that kismet or what?

Varsity jumpers are certainly nothing new, but H&M has a knack for translating trends into extremely affordable pieces that are widely accessible. So when I come across a royalty-approved trend at a £20 price point, I knew I had to share. Scroll down to see how Kate and Diana styled the preppy sweater trend and shop it for yourself. 

The late, great Princess Diana was photographed on a school run in 1992 wearing a varsity cable-knit sweater with jeans and ballet flats. 

On Kate Middleton: Ralph Lauren jumper; Superga Cotu Trainers (£55)

In May 2021, the Duchess of Cambridge wore her varsity sweater with affordable Superga trainers and black trousers for some tennis drills with kids. How cute does she look? Watch out, Sporty Spice. 

Shop H&M's New Version

Shop Other Varsity Jumpers

Next, 10 Fashion Insiders On the Wardrobe Basics They Can't Live Without

Opening image: Getty Images

Filming is underway for The Crown's fifth season, and the costumes promise to be second to none. Elizabeth Debicki, who you may remember from The Night Manager or The Great Gatsby, is set to play Princess Diana in her early 30s in the 1990s. (She takes over for Emma Corrin, who played the icon in the '80s.) Thanks to paparazzi images, we have a sneak peek of perhaps the royal's most famous outfit, second to her wedding dress: her "revenge dress." 

But first, a little background. Princess Diana attended a gala at the famed Serpentine Gallery on June 29, 1994, wearing an off-the-shoulder black dress by Christina Stambolian, a Greek designer who established her brand in London. Earlier this same day, a documentary aired, in which Prince Charles admitted to having an affair during his marriage to Diana. The timing of the event, where the princess looked positively stunning, led people to dub her look the "revenge dress." 

Now, 27 years later, Debicki has re-created the outfit with uncanny accuracy, including the hair, jewellery, dress, and sheer tights. Scroll down to see the homage and to shop pieces to emulate it yourself. 

Here, Princess Diana was being welcomed to the gala at Serpentine Gallery in London. 

This photo of Princess Diana was the 1994 version of a viral sensation. 

Here's a sneak peek of season five of The Crown, with Elizabeth Debicki as Princess Diana in the '90s. 

Re-Create the Look 

Next, Hailey Bieber wore the new platform Uggs that will sell out by December. 

At some point in the recent past, someone decided to merge the two worlds of athleisure and Princess Diana together and come up with the term "sporty and rich." Unlike the aforementioned athleisure trend, this isn't just about adding a pair of Adidas trackies to a white shirt or some other similar iteration. This is about wearing a classic sportswear piece as if you've just finished a game of tennis or are heading out of a swanky members-only club gym. 

Right now, the piece that epitomises this look is the rugby shirt for women. It's been bubbling away for a while. Ganni created an orange-and-black version adorned with sparkly buttons a couple of seasons ago, which I spotted on Abisola Omole. I've also seen Lucy Williams wearing a short-sleeved version, which is just as cool when worn with the denim of the season—baggy jeans. 

Of course, I have to, again, mention Princess Diana, who wore this top frequently but with a chic camel handbag and a pair of white jeans. During New York Fashion Week, I saw a rugby shirt paired with flowing pleated trousers and a pair of chunky black sandals, which is 100% a look I'll be wearing if we ever get warmer weather in September. If you're inspired to see how to wear a rugby shirt, keep scrolling and then shop my edit. 

Style Notes: Shorter-sleeve rugby shirts look great with a pair of loose-fitting jeans. Throw on a blazer to take this outfit up a notch. 

Style Notes: Here's proof that this top can be worn with something more glam and look incredible. Take a tip from Abi and match the colours in the top to your skirt and heels. 

Style Notes: The ultimate sporty-and-rich look as seen on Princess Diana. All you need is white jeans and a camel-coloured bag. 

Style Notes: This rugby-shirt look I've seen at New York Fashion Week is absolutely one I'll be re-creating. 

SHOP RUGBY SHIRTS FOR WOMEN

Next up, these are the biggest autumn/winter 2021 fashion trends to know. 

Given the media adoration, fashion industry attention, and overall constant press coverage, there is no denying that Princess Diana was an absolute style icon in her day. Between her haircuts and her outfits, Lady Di's looks were loved and emulated the world over in the '80s and early '90s.

Though, the true test of her fashion icon status is, undoubtedly, the fact that we're still talking about her style more than 20 years later. From the boxy blazers to the Versace minidresses, several of the late royal's most iconic looks feel more relevant than ever in 2021, and that is only supported by the fact we keep seeing influencers and fashion devotees in reimagined versions of her past outfits. 

From checkerboard-print trousers to knitted vests and colourful patterned coats, several of the trends Princess Diana championed in the '80s are now the key looks we're seeing for spring 2021. Holiday The Label has released a style of check trousers which feel very reminiscent of an instantly recognisable pair Diana was pictured wearing in 1986, while the purple knitted vest she donned as a fresh-faced 19-year-old also feels extremely modern today. 

When it comes to Diana's style, so much of her aesthetic was timeless that we often forget she too loved trying seasonal trends. Keep scrolling for three current trends that Princess Diana wore first.

Checkerboard-Print Trousers

Style Notes: These check trousers are one of Diana's most instantly recognizable looks. This winter, we've seen several influencers in new iterations of the style, as Holiday The Label's trousers (pictured below) have become extremely popular amongst the fashion set.

Shop the trend:

Knitted Vests

Style Notes: Princess Diana is pictured here in 1980 just as her engagement to Prince Charles was unfolding. However, her knit-vest–and–midi-skirt outfit formula feels very modern and is a look we've seen constantly this winter. In fact, Karina of Style Idealist is wearing an almost-identical outfit below.

Shop the trend:

Statement Plaid Outerwear

Style Notes: Colourful checks were a huge trend for autumn/winter 2021, as seen on the runways of Lanvin, Stella McCartney, and more. Here, Diana opts for a matching jacket and skirt set, while influencers everywhere are also embracing colourful coats this winter.

Shop the trend:

Next up, The biggest spring/summer 2021 trends you need to know. 

Some people are absolutely obsessed with the royals, including everything they wear, where they are going, who they are dating, and so on and so forth. I, on the other hand, am not. I mean I get it, trust me. The fact that anyone who is a royal is essentially untouchable stirs up weird feelings of obsession and wonderment as we all desperately try to get an inside look at the lives of the princesses, queens, duchesses, and more. I will admit that a lot of royals do dress well, especially Princess Diana. While that certainly is not news, after searching through archive images of the People's Princess, I found 15 outfits I personally had never seen before that really struck a chord.

The looks you're about to see here are each the perfect combination of classic and trendy. Each and every one of the outfits could be worn now and look fresh as a button. Take the below look, for example.

1. Structured Pastel Dress

I can't quite put my finger on it, but it looks like something that Staud would or already has come out with. Everything from the coloring to the buttons to the strong shoulders and tailoring has me wishing I was wearing that dress as we speak. If you like this one, there are 14 other Princess Diana outfits ahead that will inspire you to draw some inspiration from the past as you build out the rest of your summer wardrobe and start prepping for fall. 

2. Hot Pink Blazer Dress

This dress reminds me of a hot pink blazer dress I just bought and have been wearing nonstop. It's a bit shorter than this, but seeing Princess Diana in something similar solidified my purchase. 

3. Breezy Floral Situation

I'm pretty sure this is a dress she's wearing, but many brands today have been churning out similar situations in a matching set form, and now I'm definitely buying one. 

4. Hot in Houndstooth

Considering this is always a big winter trend, you better bet your bottom dollar I'm taking inspiration from this look for now.

5. Slime Time

I love that we are all up in arms about the trending slime color, but Princess Diana did it first and, if I'm being honest, did it better. 

6. One-Piece Wonder

This summer jumpsuit is everything I need in my life and more. It's breezy, easy to wear, and is clearly so timeless it hurts. 

7. Asymmetric Attire

One-shoulder pieces are trending right now across the board, but most are reaching for those asymmetric swimsuits or tanks. Well, after seeing Princess Diana rock a one-shoulder gown, that will be my inspiration for my next event.

8. The Perfect Pair

I would have never thought to perfectly match my socks to my skirt, but after seeing this look, I'm about to go on a manhunt to find socks that match all my bottoms. 

9. Casual Coat Styling 

It's the perfect kind of weather right now to wear such a cosy coat. We'd maybe swap in some jeans to go with those all-important dad sneaks.

10. The Perfect Slip

Have you ever seen a more perfect slip? I thought the answer was no until I tried to find something similar enough to shop out and low and behold, I found something with similarly thick lacy straps below. You're welcome.

11. '80s Suiting

Strong shoulders, primary colors, and unique detailing—all elements that are required for the perfect '80s suit. This was a uniform Princess Diana relied upon for a while. 

12. The Perfect Wedding Guest Dress

Need a dress for all those end-of-summer fall weddings you're going to? Well, Princess Diana was the queen of wedding-appropriate frocks, and this one just happens to be my favorite. 

13. Minimal Moment

I truly never knew a white coat, white pumps, and a contrasting necklace could look so special, but seeing Diana wear the combo here has me wanting to wear this to important meetings, nice dinners, and beyond.

14. Matching Head-to-Toe

We've seen a lot of designers send out looks for both this season and next that consisted of one colour from head to toe, which makes getting dressed insanely easy. Once again, Princess Diana did it first. 

15. Everyday Chains

Chain jewelry is one of my favorite trends right now, and if you look closely, you can see that even Princess Diana was able to incorporate the trend into even the most classic of looks. 

It hardly comes as a surprise that The Crown season four has reignited the world's fascination with all things Princess Diana. Perfectly encapsulating the royal's natural charm, Emma Corrin's depiction of Lady Di was nothing short of fascinating. And of course, along with our renewed interest in Diana's life has come a renewed interest in her ever-adored personal style. 

Season four predominantly takes places throughout the 1980s, depicting the early years of Prince Charles and Princess Diana's marriage. It was an era in which shoulder pads and feathered hair reigned supreme, and as the fashion-conscious royal she was, Diana partook in several of the decade's most iconic styles.

Throughout the series, fans get a glimpse at some of Diana's most notable fashion moments—including the blue blazer and pussy-bow blouse she wore for her engagement announcement—as well as an imagined look into her more casual, everyday attire. In fact, fans have been so enamoured by the costume design on the show that shopping app LikeToKnowIt has recorded a staggering increase in searches for various trends Diana championed. 

According to LikeToKnowIt, there has been a 7000% month on month increase in searches for large-collar blouses since the show aired, a 2900% increase in searches for pussy-bow blouses, and a 1000% increase in blue blazers over the same period of time. 

Even years after her tragic passing, it is evident that Princess Diana's iconic style remains as coveted as ever. Keep scrolling to see how these trends were depicted on The Crown and to shop the three trending looks. 

Princess Diana Costumes on The Crown 

Style Notes: This is undeniably one of Princess Diana's most iconic looks. When announcing her engagement to Charles, the royal donned a blue blazer and pussy-bow blouse, which perfectly matched the shade of her sapphire engagement ring. 

Style Notes: Throughout the series, Diana wore several statement collar blouses, which were a true hallmark of 1980s style. These looks often appeared as part of her more casual attire, and thanks to contemporary brands like Ganni, many iterations of this trend can readily be found today. 

Style Notes: Another example of Corrin's character embracing the statement oversize collar. Princess Diana wore a similar look while on a royal tour of Australia. 

1. Large-Collar Blouses 

2. Pussy-Bow Blouses

3. Blue Blazers

Next up, The biggest A/W 20 fashion trends you need to know. 

Princess Diana is undoubtedly one of the world's most talked-about style icons. From her voluminous 1980s wedding dress to the streamlined, minimalist gowns she donned in the early '90s, almost everything Lady Di ever wore has been analysed and appreciated the world over. Though there is one aspect of Princess Diana's wardrobe that has typically garnered much less attention: her off-duty outfits.

Between the cycling shorts, oversize sweatshirts, straight-leg jeans and boxy blazers, Princess Diana's casualwear choices would not look out of place in 2020. In fact, I'd happily wear many of her more casual looks today. The royal's aesthetic was so timeless it manages to transcend decades, particularly given the fact that bike shorts and everyday athleisure are reigning supreme right now. 

With a wardrobe that consisted of quality basics including tailored beige trousers, linen button-down shirts, loafers and roll-necks, many of the items Princess Diana utilised regularly are also likely already living in your existing wardrobe. 

So from gym gear to polished weekend looks, keep scrolling for five Princess Diana outfits we'd happily wear today, proving she was the ultimate off-duty muse.

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Next up, the biggest S/S 20 fashion trends you need to know. 

We've long held a fascination with Princess Diana and her era-defining style, and with the most recent season of The Crown and the fashion world's newfound obsession with all things '80s, the wardrobe of this iconic royal feels more relevant than ever. There's one Diana-approved trend, in particular, that is incredibly popular in summer 2020: the pie-crust-collar blouse. 

A mainstay of the '80s wardrobe, the ruffle-collar blouse graced many a Princess Di outfit, combining her Sloane Ranger chic with nods to trends of the day. Whether it was with pinstripe trousers or a midi skirt, the royal both demonstrated the versatility of the style and cemented its place in the fashion halls of fame. 

With 2019's fascination with covered-up silhouettes, it's no surprise that the pie-crust collar is seeing a resurgence this year. Fashion folks have been styling theirs with high-waisted jeans and boots for an authentic throwback look. Also, Alexa Chung has long been a fan of the ruffle, and if that's not a reason to try it, then we don't know what is. Scroll down to see and shop our favourite ruffle-collar blouses. 

Style Notes: There's something very 2020 about Diana's pie-crust collar and cardi. For a modern twist, try adding kick-flare jeans and heeled boots.

Style Notes: We're all about the preppy-collegiate vibes of this young Diana outfit. The bow-tie detail adds a whimsical touch to the otherwise serious ensemble. 

Shop the best pie-crust-collar blouses:

Up Next: Spring/Summer 2020 Fashion Trends: What We'll Be Wearing in This New Decade

Today in unlikely (but amazing) celebrity references, Harry Styles has seemingly taken a nod from Princess Diana's iconic '80s wardrobe. Can you blame him? Spotted in NYC, Styles wore a sheep-adorned Lanvin sweater layered over a striped button-down shirt, along with pinstripe trousers and pink loafers.

With this outfit, is it any wonder why we included Styles on our new Best Dressed Men of 2019 list? As a GQ editor pointed out, Styles's sheep sweater is strikingly reminiscent of one Princess Diana wore. She chose the whimsical sweater for a polo match in June 1983, layering it over a Peter Pan–collar blouse and pairing it with white trousers and red pointy-toe shoes. Her original sweater was from the brand Warm & Wonderful, designed by Sally Muir and Joanna Osborne, however, sadly most vintage versions are already sold out online. Scroll down to see a comparison of their stellar outfits. 

On Harry Styles: Lanvin sweater

On Princess Diana: Warm & Wonderful sweater

Shop Printed Sweaters

Next, Kate Middleton wore the $30 Zara item everyone will want. 

The jeans-tucked-into-boots styling trick is one that harks back to some of Princess Diana's most famed outfits. In one, she wore a classic '80s pair of high-waisted jeans with brown calf-high boots and in another, a double-denim getup paired with slouchy white boots. Whether it's because of the arrival of the hotly anticipated new season of The Crown or the fashion world's renewed love of throwback fashion, this Princess Di signature style has suddenly made a comeback. 

Everyone's been at it, from Camille Charrière adding a Wild West twist to a heritage blazer with light-wash jeans and cowboy boots to Katherine Ormerod bringing a more noughties vibe via black skinny jeans, knee-high suede boots and a blazer. (Kate Moss would approve.) Each one has its own personality yet still holds onto the laid-back-yet-cool energy Princess Diana was famous for. 

While the application of this trend is fairly broad (grab jeans, pull on boots, and you're done), we would recommend avoiding any baggy silhouettes in the denim department. You don't want a pantaloon situation. If you're worried about shortening your legs, just stick to boots and jeans of the same colour à la Ormerod. Knee-high boots are also helpful for adding some inches. You all set? Scroll down to see our favourite jean-and-boot outfits. 

Style Notes: Balance out the traditional associations of heritage tweed with light-wash jeans and cowboy boots.

SHOP THE LOOK

Style Notes: Make an entrance in an oversize trench, roll-neck knit and knee-high white boots à la Renata Jazdzyk.

SHOP THE LOOK

Style Notes: Bring a more noughties interpretation to the trend with black skinny jeans tucked into suede knee-high boots. Finish off the look with a pinstripe blazer.

SHOP THE LOOK

Style Notes: Nnenna Echem brings her style to the look with a vibrant check shirt, white jeans and black cowboy boots. Pearl earrings add a unexpected traditional twist. 

SHOP THE LOOK

Up next: Fashion Girls Are Buying These 10 Things From Arket This Season

Princess Diana's style has remained one of the biggest influences in the fashion world over the past 30 years with a number of her outfits proving as iconic now as they were when she first wore them. Whether you realise it or not, so much of what we wear today is inspired by the royal’s fashion choices, from her cycling short gym looks to her effortless white shirts—all still visible on the catwalks of the last few years. Trust us, a quick Google search or scroll through the many Diana tribute Instagram accounts (we advise you follow them all) will provide all the new-season inspiration you need. 

Our favourite Diana looks, though, all have one thing in common: denim. These days you don't often (or ever) see Kate, Meghan or *whispers* Camilla wearing blue jeans— but somehow Diana always managed to pull them off while still looking royal as ever. In particular, she was a big fan of the jeans-and-blazer combo, which we think might have been her secret. 

The epitome of high-low dressing, the iconic jeans-and-blazer outfit remains to this day a fashion-girl staple— likely because it makes an inherently casual wardrobe basic instantly feel pulled-together. As Diana proved, it's appropriate for so many occasions. From shopping trips to airport attire, sporting events and even speech-giving. In fact, after doing some digging into the Diana archives, we're pretty sure she's the reason our jeans-and-blazer obsession even exists in the first place... 

Keep scrolling to shop some of her most recognisable combos (and ogle at how ahead of the times she was with her looks). 

Style Notes: Without this blazer, Diana's sweatshirt and jeans outift would come across as super casual. The oversized silhouette which has inspired the likes of Balenciaga is the ultimate in power jacket. 

Style Notes: Diana confirms the outfit-enhancing, appropriate-for-anything qualities of the blazer here. Let's also note the classic Supergas which we've just added to our capsule wardrobe shopping list. 

Style Notes: So many trends in one outfit: tonal dressing, checked blazer, tights under jeans and chic ballet flats. We bow down. 

Style Notes: Diana knew the timeless elegance of a crisp shirt. Just add black jeans, a buttoned blazer and gold earrings for a look that transcends time and trends. 

Style Notes: The sunglasses, the gold hoops, the Western belt, the white jeans—this outfit couldn't be more now if it tried. 

Up next: The Trending 2021 Items That Princess Diana Wore First

There are many Princess Diana fashion eras to remember fondly and feel compelled to rediscover every now and then, but when it comes to the late royal's style applying to my own wardrobe, there's one particular moment in time that feels most relevant. As much as I enjoy the pie-crust collars of the early days or the elaborate evening gowns of her years in the royal family, it's from around 1992 to 1994 where things really start to heat up outfit-wise.

This is when Lady Di started to show just how good she looked to following a "less is more" mantra. She made over the concept of jeans and a shirt, breathing new life into a fairly staid formula with her gold earrings, tan accessories and bare makeup. Her after-dark wares became more subtle and pared back, often in monochromatic ensembles featuring body-forming sheath dresses with very little detailing and worn with matching, sleek shoes. It's when her blazer wardrobe came out to play, and we all learnt a thing or two about how this one piece of tailoring can smarten any look under the sun.

What I've realised is that Diana's most minimal outfits are made of the pieces and combinations that I keep wish listing over at my favourite online stores. In fact, COS, & Other Stories, Arket and a couple of choice others all create the kind of plain, versatile, top-quality pieces that it takes to craft a wardrobe like this. Don't believe me? Keep scrolling to see what I mean…

Even the idea of adding white pumps to anything and everything feels right for 2019.

Could Diana get any cooler with her gold-buttoned blazer and extreme sunglasses? I think not.

Never forget that a little white dress can be just as effective as a little black one.

A truly iconic outfit, and it's still so current.

When in doubt, always add chic tan accessories.

Princess Diana's signature style influenced many parts of the fashion and beauty world. Some women instantly chopped their hair into bushy bowl cuts, while others snapped up her sheep-emblazoned jumper. Other people channelled her work looks with strong-shouldered skirt suits and some emulated her going-out outfits with lamé dresses and shiny, shiny jewellery. Because a royal's life is one that's heavily documented (in how many other professions would you find yourself being photographed playing netball, getting in a helicopter and attending a gala in the very same day?), we've been able to see how Diana would dress for any occasion.

Whether in casual or cocktail attire, Princess Diana's travelling wardrobe was just as inspiring as what she'd choose to wear on home turf. Some of the most iconic looks captured from her trips abroad aren't necessarily holiday style in their truest sense (she was often working in the below snaps rather than relaxing); however, they still offer up a surprisingly current take on what to pack for a summer getaway in 2019. So much so that I've realised my suitcase looks alarmingly similar to that of the late royal's (only I've probably crammed the contents into a carry-on rather than a luxe LV trunk). I may not share the same body shape, status, look or budget, but there's an undeniable Diana vibe going on right now in my vacay shopping list—keep scrolling to see.

Safari Beige

In 1992, the prince and princess of Wales visited Egypt, and were spotted on numerous occasions both wearing rather on-theme safari-style beige looks. This colour is trending in a big way for 2019. I like Di's take on it with glam silhouettes, gold buttons and shades.

I hadn't before seen this look until today, yet the dress is so incredibly of the moment in its puff shoulder, button-through silhouette.

Minimalistic Separates

If you haven't seen this shirt-and-trouser combo all over Instagram lately, where have you been? Diana did it first in Spain in 1987 (and that's Queen Sofia with a very cute dog).

When it came to being a sensible packer, Lady Di opted in for minimalistic, elegant separates in muted tones that could be easily mixed and matched together. I've started doing the same when I travel so that I've got some failsafe outfits and can pack less.

Related: 6 New Colour Trends the Royal Family Wore First

Demure Midi Dresses

Long of hemline and sleeves, high of neck, Diana's chosen dress styles when in foreign lands echo the kind of demure styles I also like to take on holiday. This pistachio-green number was part of the aforementioned Egypt trip.

Whether printed or plain, Diana's downtime dress collection adhered to a similar silhouette at all times. 

White Accessories

Rather than the adoration the modern royals have for nude shoes, Diana was all about white accessories. They were popular in the '80s, yes, but they do also work very well in almost every holiday outfit situation.

Pictured in Australia in 1983, white bags and shoes went around the world with the late princess for many years after.

As the daughter of Grace Kelly and a longtime friend/muse of the late Karl Lagerfeld, it's no surprise that Princess Caroline of Monaco has incredible style. Like many overlooked style icons, Princess Caroline has been consistently chic for decades, having attended fashion shows and red carpets in her teens with mum, becoming a Chanel muse in the '80s and then raising another royal style icon, her daughter Charlotte Casiraghi. From her front-row looks at fashion shows in the '80s to casual preppy outfits and royal gowns, her style has always been imbued with a sense of timeless cool. Similar to Princess Diana, Princess Caroline's love of fashion comes through in all of her outfits—even on formal occasions. Keep scrolling to discover Princess Caroline's best style moments.

Style Notes: While in London in the '80s, Princess Caroline channels Diana's twist on English heritage clothing.

Style Notes: As a regular guest at Chanel shows over the decades, Caroline is often photographed in layered pearls and those iconic suits. 

Style Notes: She recently wore this couture look to a gala in Madrid, and I just love it. That bolero is a piece of art, and she carries it with so much grace.

Style Notes: See? Even the royals love an all-white casual look. The gold hoops and belt make it so glam.

Style Notes: Relaxing with her mum, Grace Kelly, she layers shell and pearl necklaces over her simple pink T-shirt and wrap skirt. 

Style Notes: Even with a five-inch tall tiara, she looks relaxed in a chiffon maxi kimono over her silk gown. 

Style Notes: I love this red floral dress she wore in the '70s in New York City with barrettes. 

Style Notes: This casual look is a lesson in simplicity. From her canvas sneakers and white trousers to the cardigan and printed scarf, this is a head-to-toe classic. 

Style Notes: This is such a hip look for a young royal. I love how she's matched her mascara to her all-purple outfit, and the double-cuff bangles are the chicest styling trick.

Style Notes: At the annual Rose Ball with her mother, Princess Grace. I love the contrast of the red taffeta and royal-blue gown.

Style Notes: As someone who would wear Chanel belts on the slopes, it's no wonder these are her protective goggles. So fashion. 

Style Notes: The oversized menswear over the little black dress is peak '80s cool.

Style Notes: This outfit is so good on many levels. The mixture of creams, browns and black is elegant, while she also subtly clashes argyle and checks.

Style Notes: Chanel chic. So simple, so good. 

Up Next: We Love Kate and Meghan, But Royal Style Doesn't Get Better Than Princess Anne's

If you connect the dots of this year's biggest trends—a paint-by-numbers of fashion's major moments if you will—you'll find yourself painting Anne Boleyn's most-famous portrait. Pearls? Check. Initial necklace? Check. Headband? Check.

At some point, did we all have this image pinned on our collective style mood board? Has our royal style nostalgia gone too far back in time? Perhaps Meghan Markle's rising star in the royal family harkens back to other "rebellious" royals, like Princess Diana and… Anne Boleyn. Regardless, it is undeniable that Queen Anne's signature look has permeated through time and onto our Instagram feeds this year. Keep scrolling to see how Anne Boleyn's style has influenced style in 2018.

A LARGE HEADBAND

Style Notes: Between the multiple royal weddings and the resurgence of '80s trends, the massive headband was bound to make a comeback. The only next step would be wearing a crown. Let's circle back on that next year.

This trend came into play midway through the year and will continue to rage on in 2019. And if the Prada one isn't exactly in your budget, there's a great shop selling the perfect velvet one on Etsy.

THE INITIAL NECKLACE

Style Notes: While Celine is responsible for the popularity of the pendant necklace in 2018, it is our dear Anne who is the OG initial necklace queen (pun intended).

PEARL SLIDES

Style Notes: After seashells, pearl slides (specifically, Simone Rocha's, and now Shrimps's pearl slides) were the most dominant accessory trend of the year. From Alexa Chung to Laura Jackson to every person at fashion week, they were everywhere.

SHOP ANNE BOLEYN'S 2018 LOOK

Up Next: Of Course, Princess Diana Has Inspired All of 2018's Top Party Trends

Countless exhibitions, a plethora of books, and many, many a Who What Wear UK article all serve as proof that the world has an infatuation with Princess Diana's style. This year, our obsession reaches yet another peak thanks to Elizabeth Debicki's spot-on portrayal of the beloved icon inThe Crown.

It's clear, from the moment Diana stepped into the royal spotlight that her outfits would be put under the microscope, however, the fascination still remains today. Looking back, it's fair to say that she was one of the most progressive dressers of her time (not to mention lineage).

Elizabeth Debicki as Princess Diana in The Crown season five.

While we're besotted with just about every aspect of her wardrobe, be it off-duty or fabulously chic, it's Princess Diana's party outfits that truly set our fashion pulses racing, particularly this at this time of the year when "party season" is at the fore of our minds. With office nights out and get-togethers on the horizon, Princess Diana's excellent array of sequinned, bejewelled, and fanciful ensembles are here to inform your own wares (or to live vicariously through).

As such, we've devoted hours to archiving our favourite Princess Diana party outfits in one place to serve as inspiration for the festive season ahead, and as a reminder of what a style star she was.

SEE PRINCESS DIANA'S BEST PARTY OUTFITS:

Style Notes: For she and Prince Charles's first public outing since announcing their engagement in 1981, Diana opts for a black strapless dress by The Emanuels. Of course, the design duo would later go on to create her magnificent wedding dress.

Style Notes: On paper, blue and white polka-dot tulle shouldn't work, but on Lady Diana for a dinner at Claridges in 1981, it was the perfect choice.

Style Notes: What's the use in being a princess if you can't dress like one? This ice-white creation looks dream-like set against her skin tone.

Style Notes: We don't know about you, but this midnight blue velvet dress, complete with on-trend lace collar, is precisely the sort of thing we'd wear today. Trust Diana to be ahead of the sartorial game all the way back in 1981.

Style Notes: While pregnant with Prince William, Princess Diana held onto her style prowess in this scarlet maternity gown by David Sassoon.

Style Notes: We'll be dreaming of sapphire sequins and spaghetti straps tonight. What a way to kick things off, Di.

Style Notes: As if the one-shoulder trend wasn't enough, Diana embraced '80s fashion in all its glory with a ruffled neckline to boot.

Style Notes: Red can be a bold hue to pull off, but it's no match for Diana. See how she's pulled out the gold accent in her dress a coordinating clutch? Masterful.

Style Notes: We don't know what we love more—the bow straps, or the Spencer family tiara.

Style Notes: We don't know what we're more impressed by—her glittering tiara or her wide metallic belt. Yes to the accessories.

Style Notes: Princess Diana wears an achingly cool tuxedo by Margaret Howell while secretly pregnant with Prince Harry at a Genesis concert. Bravo.

Style Notes: Attending the Indiana Jones and the Temple of Doom premiere in a blue satin wrap dress. This look is so 2019 that we'd gladly wear it to our office Christmas party.

Style Notes: The outfit might not say "party," but Diana's new hairstyle sure does.

Style Notes: Sequins, bows, and metallic accessories—Diana pulls out all the party stops to take in a performance of the stage show, Starlight Express.

Style Notes: Diana debunks the myth that blondes don't suit yellow.

Style Notes: Looking glam in silver lamé, we could swear we saw this exact dress on Matches last week. Diana was indeed a woman ahead of her time.

Style Notes: This Jasper Conran cream skirt suit, complete with a quirky bowtie, is so, so slick.

Style Notes: This drop pep-hem dress couldn't be more '80s if it tried—and that's precisely why we love it.

Style Notes: The diamond headband is grossly overlooked in the world of bijoux.

Style Notes: One of Diana's chicest looks to date, this embellished one-shoulder dress is a prime example of timeless style.

Style Notes: Dancing with John Travolta at the White House calls for something suitably swooshy—something we know all too well.

Style Notes: Diana proves that matching your bag to your dress is far from passé.

Style Notes: The plunging neckline, the bright satin fabric, the crystal closure… This fabulous two-piece has Alessandra Rich written all over it.

Style Notes: This dress is nothing short of fabulous—as are the mismatched gloves.

Style Notes: Proving royals needn't adhere to the nude tights rule, Diana receives top marks for her excellent use of colour hosiery. Also, must track down taffeta opera gloves.

Style Notes: In our opinion, you should never need an excuse to wear opera gloves, but the opening night of The Phantom of the Opera in 1968 is as an opportune time as any.

Style Notes: This crushed velvet dress needs to be viewed from the back to be fully appreciated. Just look at that string of pearls.

Style Notes: This dress wouldn't look out of place on the Oscar de la Renta runway. Divine.

Style Notes: Diana ensures her little black dress still makes a big impact by choosing one with interesting chain-motif straps.

Style Notes: No '80s style album would be complete without a nautical-themed dress, but Diana's is easily the most impressive we've seen.

Style Notes: Diana looks elegant in a halter neckline for the premiere of Far and Away.

Style Notes: Proving she wears suits just as well as dresses in an elegant, ivory lace two-piece.

Style Notes: Back at it again in floor-length sequins, Diana kept coming back to the trumpet dress silhouette—easily the most flattering style for her figure.

Style Notes: See? We told you trumpet silhouettes look beautiful on her.

Style Notes: Easily one of her strongest party looks, Diana never looks more stylish than when she wears cream embellishment.

Style Notes: The gold buttons give this could-be Emilia Wickstead dress a jaunty feel.

Style Notes: This would arguably become Diana's most iconic look of all time. Designed by Christina Stambolian, the dress was created for Diana three years before it received this outing in 1994. It's been said Diana was concerned it would be too daring. However, it would mark a new age in Diana's illustrious style history, and would swiftly become known as her "revenge dress."

Style Notes: For the 1995 Fashion Awards, Diana wears a navy dress by Catherine Walker, which she effortlessly offsets with a slicked-back hair 'do.

Style Notes: That's right—Princess Diana was wearing slip dresses before anyone else. We bow down.

Style Notes: One-shoulder, off-the-shoulder, halter… Diana knew the power of a sexy neckline.

Style Notes: Proof that mini dresses are anything but boring. Wearing a dress, shoes and bag in the same hue is the simplest way to make it look like you've spent hours working out to wear when, in actual fact, it only took two minutes.

Style Notes: We rarely saw Diana wear purple, but this look proves it pays to change up your colour palette.

Style Notes: Giving good suit in this double-breasted checked style. Simply switch the top-handle bag for a beaded pouch bag.

Style Notes: Continuing her penchant for embellished minidresses, Diana knows that sometimes less is more when it comes to accessories.

Style Notes: Wearing a beautifully bejewelled minidress, matching accessories and diamonds… Princess Diana's party outfits don't get better than this.

Style Notes: Princess Diana wears a sparkling Jacques Azagury gown as she attends the Tate on her birthday in July 1997.

Shop Princess Diana-Inspired Party Outfits:

This story was published at an earlier time and has since been updated.

Zara has just released an entire London-inspired collection to celebrate 20 years since it launched its Regent Street store. The British collection will make you look like an extra member of the royal family, as everything is in the Windsor family's unofficial uniform: tartan. The Brit collection includes tweed blazers, belted midi skirts, raincoats and pointed ankle boots in a distinctive red tartan.

We're using this as an excuse to dive into the royal family archive. Where better to find inspiration for how to wear heritage checks? The queen's country look always features a tartan kilt, after all. Oh, and lest we forget, Princess Diana had the most impressive tartan collection in British fashion history. Keep scrolling to see how the royals wear the print, and then shop Zara's London-inspired anniversary collection.

Related: Woody From Toy Story Is My Unlikely Autumn/Winter 2018 Muse

Shop the Collection: 

Related: 6 Items Later, You've Got a Perfect Autumn Capsule Wardrobe

Next up, see our guide to the key trends for autumn/winter 2018.

Princess Diana’s comprehensive catalogue of ’80s and ’90s outfits proves to be the gift that will forever give. Both her iconic looks are so incredibly relevant once again thanks to fashion’s cyclical nature. These decades are influencing today’s runways, street style leaders and social media influencers.

For perhaps the hundredth time this year, we’ve been back through the Princess Di archives (yes, her shoe choices and Australian tour wardrobe have been recent rediscoveries for the fashion team) in order to find excellent party looks for a story coming out next week. During our virtual travels, we stumbled upon a collection of retro winter looks that are so 2018, and we figured that it was only right to share them with you.

Whilst a handful of the exact styling constructs might have moved on in the last 30 years (not sure how you feel about a velvet tam o’ shanter?), the core of these Diana-approved cold-weather looks remains as strong as they were when they debuted.

From classic tartan pieces that chime with this autumn’s obsession for all-things checked through to the classic coat style she often turned to during those more casual public moments, we’ve selected a handful of Diana-led winter trends that you can feel inspired by now.

Scroll to see her looks and shop the current take high-street stores and designer brands are following…

1. TARTAN

Diana had many standout coats (wearing something bright and recognisable is often part of royal protocol so you can be seen easily), but this single-breasted plaid version from 1988 is really something.

In 1990, Diana took the head-to-toe tartan trend into a new decade with close-fit tailoring.

2. VELVET DRESSES

That Laura Ashley look was booming around this era, which means that demure velvet dresses were all the rage. Diana’s 1981 version with a white collar and hem is just perfect.

Another evening, another heavy velvet dress with lace detailing. This deep-blue version was also from 1981, clearly a prime time for this trend.

Related: The Duchess of Cambridge Just Found the Perfect Coat On the High Street

3. NEUTRAL SEPARATES

Don’t get distracted by the adorable William. Take a moment to notice how Diana’s 1983 combination of an off-white jumper and skirt (set against slouchy red boots) is actually very now.

If you haven’t seen this combination of neutral tailoring, a tan belt and a loose blouse on Pinterest recently, where you have you been? Diana did it first in 1983.

4. FRILLY COLLARS

Frilly pie-crust collars were a signature for Princess Di. In 1982 she wore this pink blancmange-esque extravaganza, and we’re jealous we can’t find anything quite up to scratch today. But there are plenty of frilly collared pieces out there…

The exaggerated proportions of Diana’s lace-trimmed collar and cuffs were an almost permanent fixture for the royal in 1983.

Related: These Princess Diana Fashion Trends Will Never Get Old

5. GIANT CAMEL COATS

When in doubt, put on a camel coat. The puffed shoulders and long-length pictured here certainly reflect today’s outerwear outlook—even if the hat could be left at home for we commoners.

A more casual getup from Diana proves she had quite the fabulous coat collection. This huge oatmeal cover-up from 1987 is just what we’d like to cosy up in today.

To some of us, a “fancy” gym outfit is a Lululemon sports bra or a pair of Sweaty Betty £100 leggings—but not the royal family. In fact, some of them play cricket in stilettos and throw rugby balls in Chanel. A royal tour always involves at least one run around a cricket, hockey or football pitch, however, the royals tend to sprint in their suiting rather than change into leggings. Which makes for a rather hilarious archive of “royals playing sports” pictures.

The Duchess of Cambridge has played cricket in black stilettos and a red pencil skirt suit, hockey in knee-high boots, rugby in Chanel tweed, and netball in a tailored blazer and wedges. The Duchess of Sussex is already learning how to #TrainLikeARoyal, as earlier this year, she played netball in an Oscar de la Renta blouse, Altuzarra trousers and spindly stilettos. Princess Diana might have worn cycling shorts and sweatshirts to the gym, but there are lots of pictures of her running in her finest skirts and throwing balls in heels.

Keep scrolling for our favourite looks in the “royal sports kit” bag.

Meghan Markle's Oscar de la Renta Netball Jersey

Kate Middleton's Cricket Looks

Kate Middleton's Hockey Heels

Princess Diana's Bowls Attire

Princess Diana's "Sprinter" Skirts

And all the Many Other Kate Middleton Sporting Outfits

Next up, see all of Meghan Markle's best looks to date.

This week, The Duchess of Sussex and Prince Harry will embark on an epic two-week trip to Australia, New Zealand, Fiji and Tonga — their first official royal tour together. In honour of the impending tour, we decided to look back back at Princess Diana's memorable visits Down Under. Princess Diana visited Australia several times over a decade, beginning with her first royal tour of the country in 1983 (two years after her wedding) and ending with her final trip in 1996. In between, she seemingly saved her best looks for her Aussie trips, from a very on-trend puff-sleeve dress to a sleek statement coat. Scroll down to see the best outfits Princess Diana wore in Australia and shop the 2018 versions of each look. 

Princess Diana and Prince Charles posed in front of Ayers Rock in 1983. 

The People's Princess posed with lifeguards at Terrigal Beach in 1988.

Princess Diana was photographed on her 1988 tour of Australia.

Princess Diana and Prince Charles took a stroll in the Royal Botanical Gardens in Melbourne in 1985.

Related: All the Iconic Princess Diana Outfits We Want to See on The Crown

Princess Diana met with schoolchildren in Alice Springs, Australia, in 1983.

Princess Diana wore a pastel skirt suit during her final trip to Australia in 1996.

Princess Diana was photographed at the National Gallery in Melbourne in 1985. 

Lady Di looked pretty in pink in Perth, Australia, in 1983. 

Diana, Princess of Wales, shaped the sartorial tastes of a generation. Going from young unknown bride to arguably the most famous woman on the planet, Lady Di was quite the style setter, and her looks continue to inspire us today.

Her looks became the subject of countless news stories, and her preppy-chic look helped shape the hottest trends of the '80s and '90s. Long before social media, Princess Di was the original influencer. During her courtship with Prince Charles, she was pictured wearing a pair of Hunter wellies, which immediately led to a massive spike in sales. In the '80s, she kicked off the trend for pie-crust collars and pearls.

Her style might seem conservative to us now, but it back in the day, she used her wardrobe to flout royal convention. Diana famously decided to forgo gloves when greeting members of the public, and let's not forget the famous "revenge dress" she once wore. For her, fashion was a vehicle to connect with people and even make political statements.

To mark 21 years since Princess Diana's untimely death, we decided to explore the four key fashion trends that defined her aesthetic and miraculously still stand strong today. From her off-duty outfits that pre-figured athleisure to her kick-ass power suits (which feel so A/W 18), scroll down to see our favourite looks and fall in love all over again.

Power Suits

As every royal worth their salt knows, a good suit is essential for all those formal events. It seems as though Princess Diana definitely paved the way for Kate Middleton's and Meghan Markle's collections of tailored two-pieces. There's something so 2018 about Princess Di's approach to power suits—just look at her on-trend head-to-toe beige ensemble. Her penchant for skirt suits also needs a mention, as they've made a serious comeback for A/W 18. Zara's tweed number could have easily been plucked from the wardrobe of the woman herself.

Shop the Look

Related: 51 Timeless Meghan Markle Outfits That Will Look Good Forever

Athleisure

Two words: cycling shorts. Princess Diana was so ahead of her time when it came to this divisive trend. She loved rocking leggings, sweaters and chunky trainers that wouldn't look out of place on the streets of fashion week this year. The term athleisure was yet to be coined, but Princess Di harnessed the power of the chic gym ensemble long before Kim Kardashian West became famous for it.

Shop the Look

Preppy Seperates

When she wasn't in a power suit or kicking back in sneakers, Diana was all about preppy separates. Whether it was collecting the kids from school or enjoying a family day out, "mom" jeans, boots and a blazer were the order of the day. Aside from the obvious return of '80s-style high-waisted jeans, A/W 18 sees a renewed love for Diana-inspired heritage pieces—think checked blazers and cream polo-necks. The royal also wasn't immune to the charms of Western boots, another trend that's set to surge this season.

Shop the Look

Related: How to Do Jeans and a Tee Like a Royal, According to Kitty Spencer

Printed Frocks

From her fantasy wedding gown to her little black "revenge dress," Diana's frocks make up a large proportion of her most famous looks. Her iconic pie-crust collars are echoed in the designs of-the-moment dress brand Batsheva, while the ruffled monochromatic midi she wore on arrival in Thailand bears a striking resemblance to Topshop's It polka-dot dress. Now that's what we call timeless style.

Shop the Look

Up Next: 6 Princess Diana Denim Outfit Formulas That Look Cooler Than Ever

If you were to visit an exhibition celebrating Princess Diana's fashion legacy, most of the attention would be placed on her Dior handbags, her little black "revenge dress" and the other gowns she wore for those headline-making moments. Though a pair of simple, relaxed jeans would rarely be featured in a retrospective exhibition of the fashion icon, how she wore denim is not just a source of style inspiration—it's significant too.

She ushered in a more-relaxed take on royal dressing (straight-leg jeans paired with sportswear was key to the relatable Princess Di's wardrobe). In fact, many of her off-duty outfits remain timeless and look just as good today as they did in the '90s. Keep scrolling to see and shop her six denim looks that remain relevant today.

1. Boxy Blazer + Baseball Cap

Style Notes: This Princess Diana outfit is very Balenciaga circa 2017, and an outfit we still regularly see on our Instagram feeds. We love how her straight-leg blue jeans look with her sweatshirt, boxy blazer and slogan hat.

2. White Jeans + White Roll-Neck

Style Notes: This Diana look is very "I have a Kensington postcode," as the ecru roll-neck tucked into matching jeans is a timeless (and expensive-looking) outfit.

3. Lemon Dungarees + Vintage Floral Shirt

Style Notes: This is one of Diana's most experimental denim looks, as she wore faded lemon dungarees over a pastel floral shirt.

4. White Sweatshirt + Straight-Leg Jeans

Style Notes: Diana is making us want to wear our straight leg jeans with a simple white sweatshirt.

5. White Shirt + Relaxed Jeans

Style Notes: In August 1997, Princess Diana visited Bosnia to raise awareness about landmines with a three-day visit. On the trip, she wore one of her most relaxed, but memorable, outfits: a white shirt, blue jeans and Tod's loafers. She arrived on the trip in a similar elegant denim look, wearing black jeans with a pink Ralph Lauren shirt.

6. Leather + Black Denim

Style Notes: For her day on the log flumes at Thorpe Park, Diana wore slightly faded black jeans with brown suede Chelsea boots and a black leather puffer jacket.

Click here for more Princess Diana style inspiration.

Many of the biggest icons of the '90s and '00s are being analysed once more by fashion editors across the globe: Carrie Bradshaw's most recognisable looks feel current again, for example, and there's clearly a renewed interest in the wardrobe of the late Princess Diana. We've enjoyed rediscovering Diana's many looks for Wimbledon or Ascot, and revisiting the wonder of her wedding dress, and with all of the hours of image research we're putting in, it's clear to see there's another correlation between 2018's fashion outlook and Diana's elegant outfits.

Her shoe choices in particular have come full circle. Not so long ago, kitten heels, slingbacks and other epoch-defining details of '90s footwear were decidedly out. Now, when you look to Instagram's hippest influencers and to the brands we most commonly follow into new-trend territory (hi, Ganni) these references are au courant once more. Fashion insiders predicted it early when the resurgence of Manolo Blahnik's spindly stilettos or jewel-fronted mules kicked in, but the trend has now filtered through to the high street, with brands such as & Other Stories stocking the kind of strappy disco sandals we all bought decades ago.

Keep reading to see how Diana wore and styled these shoe trends first, and shop the new-in pieces to get the look today.

Baby-blue satin is obviously the ultimate option, but any fancy kitten-heel slingbacks will make us happy right now.

Related: Lady Kitty Spencer Just Wore the Most Princessy Dress and Tiara of All Time

Sassy lilac suit? Check. Pearls? Check. Contrast-toe pumps? Check.

Okay, a) we hadn't seen this dress before on Lady Di, but also b) just look at how 2018 those strappy little evening pumps are. Back in the day, Diana wore Jimmy Choo on repeat, and the designer does a similarly elegant style today.

Related: Princess Diana Has Inspired Everything I've Ever Worn

See? The '90s are so back.

If it were any other year, Wimbledon would currently be taking place in London. Though, if there's anything we know to be true, it is that 2020 is no ordinary year. While this year's tennis tournament may be cancelled, we can't help but reminisce on the immaculate courtside style of Wimbledon's past.

Of course, you can't talk about Wimbledon style without mentioning Princess Diana, as she always had fun with her tennis looks. Diana was a keen tennis player herself and often looked amazing on the court in her cycling short and pleated miniskirts. Her courtside looks are just as memorable, however, as she often watched Wimbledon in pastel suits, bold accessories and vibrant prints that we would look just as fabulous today. In particular, we love the sleeveless red tuxedo-style dress she wore with oversize gold buttons and the purple printed blouse which looks like it could be a Rixo print. 

Keep scrolling to see the seven aces Princess Diana served at Wimbledon.

1. Gold Buttons

Style Notes: Princess Diana loved gold buttons, and at the 1994 championships, she wore a sleeveless red tuxedo-style dress with penny-size buttons. It's a heatwave-proof winner.

2. Purple Print

Style Notes: In 1991, Princess Diana watched the tennis with a young William wearing a white pleated skirt with a purple printed blouse, cinched with a wide white plaited belt. 

3. Interesting Layering

Style Notes: In 1981, Diana experimented with unlikely layering at Wimbledon, wearing a white classic shirt underneath her printed blouse and skirt co-ord. It's an unlikely pairing, but we're into it. 

4. Short-Sleeve Blazer

Style Notes: In1994, Princess Diana wore a black-and-white short-sleeved double-breasted jacket with statement gold buttons. Very Alessandra Rich, no?

5. Piled-On Gold Jewellery

Style Notes: Princess Diana's 1993 Wimbledon outfit was a real winner, as she wore a pale pink suit with statement gold buttons, a pink polka-dot silk blouse and a heavy gold chain necklace. 

6. Pastel Suiting

Style Notes: At the championships in 1995, Diana wore a pale lemon skirt suit, making us want a pastel suit more than ever. 

7. Millennial Pink

Style Notes: At one of Diana's earlier tennis appearances in 1988, she wore a pretty pink jacket and matching skirt.

For more of Princess Diana's style, see the 22 outfits we never tire of looking at. 

Some have Instagram girls, others have the Net-a-Porter 'New In' page, but I have Princess Diana. In a world flooded with visual inspiration and ever-changing messages about what’s in and what’s out, I always return to my failsafe WWDW mantra—that’s What Would Diana Wear?

My fascination with all things Diana style-related goes back as far as I can remember and can mostly be blamed on my Mum’s love of Hello! magazine. Growing up in the mid 90s, there was always a stack of copies in the house and- strange as it may have been for a little girl who wasn’t quite ten—I would happily spend hours leafing through the pages, studying this impossibly glamorous woman.

Diana wearing a white Versace dress attending a concert in Italy, 1995.

One week, she would be wearing Versace Haute Couture for a museum benefit, the next she’d be in her continental chic uniform of chinos, a crisp shirt and Tod’s loafers as she made a charity visit to Africa. This wasn’t the kind of frothy, tulle-clad Princess I’d learnt of in Disney films and seen through as being a totally unrealistic fashion muse, but a template for how to dress like a grown-up and an intoxicating introduction to the power of fashion—the first bag I really, really wanted was not a Mulberry Bayswater but a Dior Lady Di.

At Guards Polo Club wearing a British Lung Foundation sweatshirt with jeans tucked into boots and an oversized blazer, 1998.

As I got older and swapped Hello! for Google Image searches, I fell down a rabbit hole of Diana pictures from the eighties which added an entirely new element to my fascination. I witnessed how her style had evolved from the frilly prettiness of her wedding dress (will there ever be a more romantic bridal gown?) and days as a young mother in acres of chiffon to the power princess glitz of embellished ballgowns and wide-shouldered skirt suits. At times she looked hilarious (like when she wore a maple leaf-collared dress for a visit to Canada), while at other times she looked like the woman you want to be; her pearl-encrusted 'Elvis' look by Catherine Walker or a one-shouldered dress by Japanese designer Hachi are the ones I’d take in a heartbeat. And who can forget the Christina Stambolian LBD she wore the night that Prince Charles confessed to adultery?

At the polo in Cirencester wearing a floral pencil skirt with red accessories and a red shoulder-robed sweater, 1985.

Related: 51 Timeless Meghan Markle Outfits That Will Look Good Forever

The best bit though was, and still is, off-duty Diana. At the polo, she proved that she had genuine personal style when she paired sailor-collared blouses with floral pencil skirts or jeans with a sweatshirt and cowboy boots. She was athleisure’s earliest adopter: see the cycling shorts and chunky trainers she wore to work out at her gym, the Chelsea Harbour Club, below. And her failsafe jodhpurs plus blazer plus polo neck formula for lunches out looks as good today as it did in 1995.

In a tuxedo suit (designer unknown) for charity concert appearance at The Royal Albert Hall, 1990.

These days, my love for Diana’s style has become a professional obsession. As fashion news and features director at The Telegraph, our readers can’t get enough of the royals. Last year, twenty years since her death, we wrote about Diana’s impact on fashion. I have been lucky enough to interview her stylist, Anna Harvey, and the designers she loved to work with. One anecdote which stuck with me was Jasper Conran remembering how Diana had come to his studio one day saying she was fed up with evening dresses, so he had made her a series of tuxedo suits- it was a move which seemed radical when Meghan Markle did it earlier this year so I can only imagine how many eyebrows Diana must have raised 30 years before.

You can hardly move on Instagram for throwback imagery of Diana (@flyladydi_ and @princess.diana.forever are my favourites) which I think proves I’m not alone. I knew this for sure when Off-White designer Virgil Abloh dedicated his spring/summer 2018 collection to the Princess; his moodboard and images of Naomi Campbell wearing a modern take on Diana’s beloved cycling shorts went viral.

Wearing the famous "Revenge Dress" by Christina Stambolian, 1994.

It’s also about attitude. Diana was never afraid to experiment, or to update her look according to where she was in her life and what was in vogue at the time. She’s a poster woman for embracing a trend if you love it or breaking the rules if you feel like it (she was the first royal woman to abandon wearing gloves). She embraced sleek minimalism as gladly as bold prints and jewellery. While we might not all have a necklace from the crown jewels to wear as a headband instead (yes, she did that), we can all get on board with that approach. In short, next time you get dressed, I urge you to ask—what would Diana wear?

The Prince and Princess Of Wales at an official dinner in Nova Scotia, Canada, 1983.

Related: The 7 Fashion Aces Princess Diana Served at Wimbledon

So how is Diana’s style still relevant in 2018? Admittedly, some of those mid-'80s looks are to be approached with caution but there's a great deal that feels right for now. 

Lady Diana Spencer (before she married Prince Charles) wearing a signature pie-crust blouse, 1981.

Keep scrolling for the 3 Diana-inspired looks that are working for me this year…

Diana Trend #1: Shorts With Everything

This summer, I’ve taken inspiration from her penchant for wearing high-waisted shorts with her sleek swimming costumes as an alternative to boho kaftans.

In cycling shorts for a gym visit, 1998.

Diana Trend #2: Jeans, Shirt and Loafers

My go-to uniform on those mornings when I wake up and can’t think what to wear is her prototype of loafers, jeans, a shirt and blazer, although a classic shirt can be swapped for a pie-crust collar one for a Lady Di meets '90s Di mash-up.

Princess Diana in jeans, a shirt and loafers for a visit to Bosnia during her campaign for landmine awareness, 1997.

Related: Meghan Markle Just Wore Princess Diana's Signature Outfit to Buckingham Palace

Diana Trend #3: Polka Dots

I love anything polka dot, but there's an abundance of spotty dresses available right now, so that is perhaps the easiest and most modern route in.

Princess Diana in a spotty blouse at the polo in Windsor, 1983.

Hands up if you share my obsession!

Princess Diana’s most iconic outfits may have been styled back in the ’80s and ’90s, but as you may have noticed from her impeccable wedding guest looks to her style signatures, a lot of her best looks are still super relevant. We’ve even spotted the likes of Zara tapping into some of Diana’s most beloved trends.

So it makes perfect sense that since Diana’s style has made an everlasting impression on us all—her go-to outfits for a day at Royal Ascot are totally worth taking inspiration from in 2019. What to wear to the races can be a tricky outfit dilemma, especially when dress codes and formal traditions come into play. But follow Diana’s lead, and you’ll be styling up endless looks from polka dots and pencil skirts to statement hats in no time.

Keep scrolling to see our pick of Princess Diana’s best Royal Ascot outfits, with all the shopping you need down below.

Polka dots head to toe.

It was a big year for accessories in ’97—just check out the floral trimmings on that straw boater.

Related: These 35 Wedding Guest Dresses Are Next-Level Beautiful

This bold turban hat is giving us life.

When in doubt, go all pink. We’ve got a lot of love for the strong polka dots on Sarah Ferguson here.

Chic separates don’t always need to be colour co-ordinated. Here’s the proof.

Never underestimate a good hat.

Going for a bold print? Take a tip from Diana and accessorise in just one colour.

Related: 36 Iconic 1980s Fashion Moments We Never Want to Forget

Simple yet super sleek.

Navy and white always looks classy.

The full look in all its glory.

You can't go wrong with a nautical nod.

This is giving us Pretty Woman vibes.

Take away the purple accent, and this is a full 2018 look.

Pencil skirts and power shoulders.

So chic.

White tights were a royal favourite back in the '80s.

This soft peachy shade is all over the high street at the moment.

Keeping things classy in grey, white and a timeless string of pearls.

Candyman stripes and bright red may not be for everyone in 2019, but there's no denying this is Instagrammable.

From the car-bonnet post to the puff-shouldered skirt suit, this is everything.

Next up, the summer shoes royals always wear.

This story was published at an earlier time and has since been updated.

All celebrities are scrutinised (and always have been), but the members of the royal family are watched, discussed and judged with an intensity that's unmatched. It's believed that around 2 billion people around the world watched Prince Harry and Meghan Markle's wedding. The royal family is an institution that's steeped in tradition and formality, and while it does evolve and modernise, it does so at a gradual pace. Since clothing determines how we represent ourselves to the world, it's understandable that there's a lengthy set of wardrobe-related protocols that the royal family must adhere to on royal tours and official visits.

In the spirit of the royal family's newest member (Meghan Markle, in case you forgot), we're highlighting some of the major wardrobe rules that she's going to have to get used to.

Can't Wear: Anything Too Low-Cut

While a turtleneck isn't required, modesty is the best policy in the royal family, so you won't find many (if any) cleavage-baring tops in their closets.

Can't Wear: Flat Sandals

Kate Middleton very rarely wears open-toed shoes at all, but when she does, they almost always have a heel. Hence the countless pictures of her playing sport in wedge espadrilles. When she wants to wear flats for a less-than-formal occasion, she sticks to ballet flats, boots or white sneakers. That said, her most-worn shoe style is classic pumps.

On Kate Middleton: Emilia Wickstead Dress

Can't Wear: Bare Legs/Short Hemlines

While this tradition is said to be loosening up, royal family members usually wear stockings with dresses and skirts for formal occasions, and short hemlines are a no-go. (We fully expect Markle to ignore this "rule" on occasion, as she did for her and Harry's engagement photos.)

On Meghan Markle: Goat Flavia Silk-Crepe Pencil Dress (£590); Philip Treacy fascinator

Can't Wear: Large Handbags to Events

While Markle has opted for totes, crossbody bags and sizable top-handle satchels in the past, she's been carrying clutches more and more as of late, as most royal family members almost exclusively do. (It's said to help them avoid awkward handshakes and cover up cleavage when exiting a vehicle.)

On Kate Middleton: Boden coat

Can't Wear: Fabrics That Wrinkle Easily

Say goodbye to delicate linen and silk if you join the royal family. In order to maintain a polished appearance, they opt for heavier fabrics that won't easily crease (e.g., tweed or wool). Fun fact: Princess Diana's wedding dress received criticism for being made of a crinkly fabric.

On Princess Eugenie: Fiona Graham hat; Gainsbourg dress; M2Malletier bag; Valentino shoes

Can't Wear: Black to Daytime Events

Unless it's a funeral or another sombre occasion, the royal family steers clear of black during the day and instead opts for colours that help them to easily be seen in a crowd.

On Meghan Markle: Carolina Herrera dress

Next up, see Meghan Markle's most stylish looks to date. 

Of course, everyone is acquainted with Princess Diana's charming sons, but how much do you know about the late royal's niece? Lady Kitty Spencer is the eldest daughter of Diana's brother, Earl Spencer, and happens to be a budding style star. You can spot the 27-year-old at the most stylish events around England—from Meghan Markle and Prince Harry's wedding to Topshop's front row (next to Kate Moss's younger sister, naturally).

As for her outfits, Spencer favours A-line silhouettes and is rarely seen without heels. She's also a model with Storm Management and has walked the runway for Dolce & Gabbana (which explains why she wears the brand regularly). Dying to learn more about her? Spencer's Instagram is definitely worth a follow. Scroll down to see our favourite outfits from Lady Kitty Spencer.

On Kitty Spencer: Dolce & Gabbana dress; Bulgari High Jewellery necklace in platinum and yellow gold

On Kitty Spencer: Dolce & Gabbana dress; Bulgari jewelry

On Kitty Spencer: Bulgari jewelry

On Kitty Spencer: Manolo Blahnik shoes

On Spencer: Bottega Veneta dress

For more royal style, see Meghan Markle's best looks ever.

As if the slinky halter-neck Stella McCartney gown, nifty sports car and a rather dashing prince in a velvet tuxedo weren't enough to extend our gawps, Meghan Markle just piqued our interest even further en route to the wedding reception by waving an enormous emerald cut aquamarine and diamond ring into view. The ring was so mighty that not only could it warrant its own postcode, but it is also important enough to lay claim to its own heartwarming royal tale.

This beautiful whopper of a gem was first owned by Diana, Princess of Wales. It was custom made following her 1996 divorce from Prince Charles: She felt it inappropriate to still wear the original sapphire ring from Garrard and commissioned an alternative to better suit her tastes at the time. “She always chose diamond jewellery that was meaningful to her—she was very intentional with her jewellery choices and made sure they were the best representation of those meaningful moments,” Grant Mobley, a gemologist and Director at Pluczenik, tells the Express, estimating that one would expect to pay around the £75,000 mark today for such a unique creation.

As many of you may recall, following Diana's untimely death, the icon had requested that three quarters of her £21 million estate and her personal jewellery collection was to be put aside for her boys—Harry and William—to inherit. Her wish was for the sons to save these heirloom pieces for their future wives—and they have dutifully followed. Harry originally chose a sapphire ring and William opted for a Cartier watch, however, when William was set to propose to Kate Middleton, the younger brother stepped up as the sweet sibling we'd always imagined him to be and offered to do a swap. That means Catherine, Duchess of Cambridge, owns the £300,000 12-carat sapphire-and-diamond cluster ring while Harry used some diamonds from a brooch of Diana's in order to sandwich a Botswanan jewel for Meghan's engagement ring. In addition to those diamonds, it would now appear that this aquamarine ring—photographed above on Diana almost exactly twenty years ago—will also be adopted by the new Duchess of Sussex.

With Meghan surely kickstarting a trend for simpler, lace-free bridal gowns, could we also be looking at a rise in requests for coloured (and/or square, art deco–style) stones in wedding and engagement rings? Our gut feeling says yes—especially when you look at how that blue pops against her elegant white maxi.

Shop Aquamarine Rings Inspired by Meghan and Diana

Bulgari Le Magnifiche Creazioni

Price availble upon request.

Related: All of the Guest Outfits You HAVE to See From Meghan and Harry's Wedding

Boodles Malham Rock Aquamarine Cushion Ring 

Price availble upon request.

Congratulations, Meghan and Harry. We can't wait to hear about the reception…