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!

Eugénie Trochu is a Who What Wear editor in residence known for her transformative work at Vogue France and her Substack newsletter, where she documents and shares new trends, her no-nonsense approach to fashion and style, plus other musings. She's also working on her upcoming first book that explores fashion as a space of memory, projection, and reinvention.

There are clothes you choose, and then there are the ones you slip into without thinking—almost like opening a window in spring. There's that vague sense of freedom even though you know perfectly well it's still a little cold. The oversize logo sweatshirt belongs to that category. It's a comfort piece but never entirely neutral.

It's never anonymous. There is always something written on it—a team, a university, a club. Baseball, basketball, American football, ski club, tennis. There are words you don't necessarily know but that you wear anyway. A slightly faded logo, a hoodie that's too big, a sweatshirt that suggests more of an idea than an actual practice. You're not here to play. You're building a silhouette. You borrow an identity the way you'd borrow a holiday house: without really knowing who lived there before but with the quiet sense that you belong.

In France, the hoodie still feels slightly suspect. We like it, but we edit it. We temper it and make sure it doesn't spill over. Elsewhere, it moves freely without justification. You think of Princess Diana, of course—a Virgin Voyages or Harvard hoodie, bike shorts, dark sunglasses, and that detached ease. It's a silhouette that has become almost theoretical. But there are also her more unpredictable combinations: jeans, cowboy boots, a printed white sweatshirt, a sharp-shouldered blazer, and a cap. It's something slightly chaotic, almost bohemian in spirit, yet perfectly controlled. That's probably what fascinates—a kind of freedom that is, in reality, extremely constructed.

Does it work because it's her? Probably, in part. I am not Diana, and here is what I've learned from wearing it in France.

The oversize logo sweatshirt doesn't tolerate literal styling. Worn at face value, with everything else following the same logic, it becomes an outfit, almost a uniform. What you're after is a silhouette, so you offset it. An XXL hoodie with a slightly dramatic fluffy coat and leopard trousers. A collegiate sweatshirt with perfectly cut flared jeans. A slightly adolescent logo with kitten heels and capri pants. There always has to be tension, a subtle contradiction. Otherwise, it doesn't work.

Shop My Top Logo-Sweatshirt Picks

Princess Diana's style never gets old. Even though trends have come and gone and new fashion icons have been minted in the intervening decades, the late royal's outfits continue to inspire people in 2026. Case in point: Hailey Bieber's spring style. I don't know if Princess Diana is actually on Bieber's mood board or not, but I see several strong through lines between the two women's closets.

Certain colors, patterns, and pieces Bieber wears remind me of Princess Diana's spring and summer wardrobe from the '80s and '90s. When Bieber wore black-and-white polka-dot capri pants, for instance, it instantly made me think of the late royal's love for the same colorway and print. Plus, while Diana never wore polka-dot capri pants specifically, she did have a love of printed pedal pushers, including a pink gingham version. Scroll down to see and shop four spring trends that both women have in common.

1. Black-and-White Polka Dots

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2. Rugby Shirts

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3. Lime Green

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4. Leopard Swimsuits

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In 1981, Princess Diana attended a polo match. So far, so par for the course. At this particular polo match, though, the Princess of Wales opted for a very youthful spring look consisting of butter-yellow—OMG, did Diana start that trend 40 years early?—denim overalls layered over a floral bib shirt. Of course, being Diana, she edge-ified the look with a pair of classic espadrille wedges in raspberry red, adding height, dimension, and a touch of daring. Frankly, those shoes were a natural pick for this particular outfit.

The princess further accessorized with cool-girl oversize pilot sunglasses, simple chunky gold hoop earrings, and a stunning quilted, floral, rectangular bag by French label Souleiado, which—surprise!—you can actually still buy today. Diana brought it out again throughout the '80s and '90s. Besides being cute and eminently springlike, the great thing about this look is how mismatched everything is: clashing floral prints, pastel yellow paired with bright red, a conservative silhouette with edgy accessories. It's so much fun and still totally current for spring 2026.

Re-Create Princess Diana's Look

I’ll admit that when I’m scrolling through Getty Images, I often find myself falling down a royal fashion rabbit hole. Recently, while doing some very important research (read: looking for festive outfit inspo), I searched "Princess Diana Christmas" and sorted by "most popular."

The results were a master class in holiday dressing, ranging from early '80s charm to sophisticated mid-'90s tailoring and turtlenecks. These ensembles truly captured the internet's heart—and mine. Photo archives are digital time capsules of the people's princess, revealing how her style evolved from the ruffled, shy charm of a new royal to the confident, monochromatic power dresser we still reference today.

Keep scrolling to learn more about the three looks that are forever on the ultimate royal holiday mood board.

1981: Diana opted for a soft blue coat with flowers and a delicate pillbox hat for her first Christmas at Sandringham, embodying the quintessential "English rose" aesthetic.

1990: This vibrant purple coat with a matching velvet hat was a Christmas Day showstopper, showcasing her love for bold jewel tones and textured millinery.

1994: Diana’s best Christmas look is this sophisticated monochromatic brown ensemble from 1994, featuring a structured coat, brown booties, and a matching fur hat.

Re-Create the Look

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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Every season is Princess Diana season because even close to three decades after the royal's tragic passing, her style remains both timeless and aspirational—all while being eminently achievable for us common folk. Among other things, Diana showed us how to style capri pants in the spring and jeans tucked into boots in the fall.

Speaking of knee-high boots, the late Princess of Wales loved a boot-and-midi-skirt moment—a styling trick which the current Princess of Wales, aka Kate Middleton, clearly learned from her. There's an iconic photo of Diana bringing baby Prince Harry(!) to school while wearing the uniform: bunchy brown leather riding boots under a glorious chocolate suede ankle-length belted skirt. The crowning jewel of it all, if you will, was the white turtleneck balloon-sleeve sweater she tucked into it, casually, as if she hadn't given it a second thought. As ever, the outfit was perfect and thought-through without being try-hard. Also, somehow, it's totally current for 2026—even though the picture was taken in 1988. Go figure.

Re-Create Princess Diana's Outfit

I've never binged a TV show faster than All Her Fault. I watch a lot of television, so that's really saying something. I flew through all eight episodes in less than 48 hours, but if it weren't for my pesky job, I'd have finished much sooner. Sarah Snook and Dakota Fanning don't need to do any more press for the show, since it's already garnered so much word-of-mouth attention online. Fittingly, Fanning was photographed in Los Angeles enjoying some much-deserved downtime post-Oscars. She wore a Dodgers hoodie, flip-flops, and The Row's highly coveted Margaux bag.

You know who else liked to combine oversize sweatshirts with designer bags? Princess Diana. The late fashion icon was a master of high-low dressing. Princess Diana collected handbags from brands like Dior, Chanel, Salvatore Ferragamo, Gucci, and Tod's, so I have a feeling she'd love The Row, too. The only difference: Fanning swapped sneakers for flip-flops—she does live in L.A., after all. Scroll down to see Dakota Fanning's newest off-duty outfit.

Dakota Fanning nailed high-low dressing in a baggy hoodie and a purse by The Row.

In January 1997, Princess Diana wore a casual oversize sweatshirt with a croc Versace bag.

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Princess Diana wore many iconic outfits during her time in the spotlight, but none were quite as memorable as her "revenge dress." The black dress, designed by Christina Stambolian, earned its moniker after the princess wore it on June 29, 1994, the same day Prince Charles admitted on television to having an affair. As we all know, looking good is the best revenge, right?

Thirty years later, the outfit is still symbolic of Princess Diana's strength of character and impeccable style. It's only fitting, then, that a fashion lover like Elsa Hosk would pay homage to the legendary look on Halloween. Hosk re-created the "revenge dress" to perfection in 2024, and I'm still thinking about it to this day. "You win," Sofia Richie Grainge commented on Hosk's Instagram at the time. Yep, I couldn't agree more! In my opinion, Hosk managed to style the look better than the professional costume designers on The Crown. Impressive. Scroll down to revisit Hosk's chic tribute to one of history's best dressed women.

Princess Diana in 1994

Elsa Hosk in 2024

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While I understand why some people don't like to compare the current Princess of Wales to the late Princess Diana, I find it fascinating to examine how royal style has evolved (or stayed the same) over the years. My discussions are purely sartorial in nature and are never meant to pit the two women against each other. It's not a competition! On the contrary, I enjoy celebrating how each has left a mark on royal fashion in her own way. Both women have consistently proven that royals can set trends while working within the confines of their roles.

One of the clearest examples of this evolution across generations of royals is Kate Middleton's newest outfit. Echoing a classic Princess Diana formula, Princess Kate wore an A-line midi skirt with knee-high boots and a blazer. The only difference? Kate modernized Diana's look by opting for a cropped jacket instead of a full-length one. This small tweak creates a fresher, more contemporary silhouette while still nodding to Diana’s classic approach. Scroll down to see how the looks compare.

Kate Middleton's New Skirt-and-Boots Outfit

On Kate Middleton: Me + Em Suede Cropped Military Jacket ($475); Ralph Lauren Collection Brown Birdseye Tweed Evilyn Skirt ($2100); Polo Ralph Lauren belt; Gianvito Rossi boots; Spells of Love earrings; Sudbury Silk Mills Shop scarf

Princess Diana's Outfit From January 1991

Re-Create Kate Middleton's Newest Outfit

From her philanthropic endeavors to her views on royal life, Princess Diana was ahead of her time in many ways. Her fashion choices were similarly trailblazing, which is why she remains a style icon nearly three decades after her passing. Some elements of her outfits might not be in style anymore—'80s shoulder pads, anyone?—but others are still incredibly relevant. Case in point? Superga sneakers.

As soon as I saw Julia Roberts wearing Superga 2750 Cotu Classic Sneakers ($70) at the Venice Film Festival, my mind immediately went to Princess Diana, who also owned the shoes in the same navy colorway. Emily Ratajkowski and the current Princess of Wales, Kate Middleton, are also fans, but they both prefer to wear white Supergas. (Not to brag, but I've also worn them for nearly a decade.) Scroll down to see how Julia Roberts styled the classic sneakers at the airport in Italy this week.

On Princess Diana: Superga 2750 Cotu Sneakers ($70)

On Julia Roberts: Superga 2750 Cotu Sneakers ($70)

Shop the Sneakers in 6 Different Colors

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:

What goes around comes around. In the '50s and '60s, pedal pushers peaked in popularity. (Say that five times fast.) The era's biggest stars wore them, including Marilyn Monroe, Audrey Hepburn, and Grace Kelly. Since then, they've gone in and out of style, notably surging in the '80s and again in the early 2000s. I haven't worn them since middle school, but I have a feeling that's about to change.

While browsing Reformation's new arrivals, I stumbled upon a pair of pink gingham pedal pushers that immediately made me think of Princess Diana. The late icon wore an incredibly similar pair in July 1986 at Highgrove House styled with a coordinating pink sweater. Reformation's new pants go against the grain because the last several years have been marked by full-length, baggy silhouettes, and slim-fit, cropped pants have fallen by the wayside. Thanks to Reformation's endorsement, however, I think pedal pushers are due for a major comeback this spring. Scroll down to shop the Reformation pair in question as well as other options inspired by the people's princess.

Princess Diana's Gingham Pedal Pushers in 1986

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Carolyn Bessette Kennedy and Princess Diana are the penultimate '90s style icons. I know Who What Wear's fashion editors agree. They were both known for their understated yet elegant aesthetic—CBK for her cool, minimalist street style and Princess Diana for her casual, off-duty looks (oversize sweatshirts and bike shorts are a foolproof outfit formula I'll never stop using). Simply put, they pioneered the "quiet luxury" trend long before that term existed.

Their beauty aesthetics were similar. Oftentimes fresh-faced and paired back, they weren't ones to participate in the era's bolder trends. I've always suspected that their fragrance preferences followed suit.

After doing some digging, it seems like CBK wore Egyptian musk oil and Princess Diana preferred floral-woodsy scents. Nonetheless, I'm convinced they'd both approve of one of 2025's trending fragrance categories: so-called "skin scents."

What Are Skin Scents?

Skin scents are subtle. They're not too floral or woody, and they contain musky, lingering base notes that give them a warm and grounding quality. Since they effortlessly mingle with the skin's natural scent, they make people say, "You smell so good," rather than, "What perfume are you wearing?"

Ines Guien is a fragrance expert and the VP of Operations at Dossier. In general, skin scents are lighter and fresher and project a 'your skin but better' vibe." Depending on the other notes in the formula, you can "take it any direction you want," whether that's something light and fresh or slightly stronger or spicier. Both give you the 'second skin' effect in different ways."

In my opinion, skin scents are the epitome of "quiet luxury." They're not too strong or overpowering, yet they envelop the wearer in a warm, alluring scent. It's the reason I think CBK and Princess Diana would approve of them in 2025.

What Is "Musk" and How Is It Incorporated Into Skin Scents?

Take a look at the top-trending skin scents, and I bet my bottom dollar that musk or skin musk is listed as a key fragrance note. Musks were traditionally derived from animal sources but have been reinvented through modern perfumery to offer ethical and sustainable alternatives," Guien says. For example, the musks used at Dossier are vegan and cruelty-free.

Whether it's listed as "musk" or "skin musk," it all boils down to the same thing. "Today’s musks, often referred to as skin scents, provide a clean, soft, and intimate fragrance that mimics the natural scent of human skin," Guien says. These compositions are designed to be subtle yet captivating, enhancing the wearer’s natural aroma without overpowering it."

Why Are Skin Scents Trending Right Now?

CBK and Princess Diana aside, skin scents are one of 2025's trendiest fragrance categories. Guien says it's because they suit everyone. "Skin scents give you that 'my skin but better' scent that works for every outfit, occasion, or mood. They’re clean yet sensual with this seductive, almost magnetic pull. They’re the perfect everyday scent for day or night. Skin scents are also great for layering (layering is also another trend in fragrance right now) to create a 'unique to you' scent."

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Kim Kardashian has finally brought out Princess Diana's cross necklace, which she purchased at an auction in January 2023. While appearing on the red carpet at the 2024 LACMA Art + Film Gala on Saturday, the Skims founder showed off the extravagant bauble with an extra-deep V neckline.

The necklace, known as the Attallah Cross, is made of amethyst, diamond, gold, and silver. Kardashian acquired it in an auction at Sotheby's London last year for the modest sum of $197,453. As CNN reported, the impressive piece of jewelry was originally purchased by the late businessman Naim Attallah CBE in the '80s, and he loaned it to his friend, the former Princess of Wales, a few times. The late royal was the only person known to have worn the amethyst cross before Kardashian.

The reality star let the royal jewel do most of the talking on the night, complementing it with a Bulgari pearl and diamond necklace, a Tallarico pearl choker, and a custom Gucci dress and coat in a sumptuous shade of cream. Her longtime hair stylist, Chris Appleton, styled her locks in a dark bob with a sculpted flick across her forehead, using Bellami hair clip-ins.

Kardashian attended the LACMA Gala alongside the likes of Charli XCX, Viola Davis, Chloë Sevigny, Blake Lively, Kaia Gerber, Yara Shahidi, Anna Kendrick, Greta Lee, and so many other It girls.

On Kim Kardashian: Custom Gucci coat and dress; Tallarico choker; Bulgari necklace; Princess Diana's Attallah Cross necklace

I’ve always been a city girl. I was born in Kuala Lumpur, grew up in Houston, and upon moving to L.A., lived comfortably east of the 405 for years. But a California hazard they don’t warn you about is that you might meet a cute surfer who eventually lures you all the way west. After some cajoling, I gave in to my inner Pisces, packed up my gray Tabby, and moved us across town to the sun-dappled, salty-aired streets of Venice Beach.

It’s been six years since, and while I may not yet be a bona fide beach babe (I still prefer reading on the sand to roaring waves), it’s home. My hair is blonder, my mornings slower, and I love the neighborhood's walkability and proximity to the Pacific Ocean. Every time I catch another glorious pink sunset, it does feel a little like living in a fantasy.

If you've ever experienced L.A. traffic, you know how vast and sprawling the city is. Different zip codes mean different dress codes, and the attitude in Venice is very relaxed. Denim and comfy shoes reign supreme, and a knit is a must to combat the almost-always-present marine layer. Most of my bolder pieces have been relegated to the back of my closet, awaiting invites for martinis at Tower Bar, dancing at A Club Called Rhonda, and too much pasta at Little Dom's. So while my highlights may not be low-maintenance, my approach to daily dressing is.

Keep reading for three of my tried-and-true outfits for your next trip to the beach.

JEANS + EASY COAT + WESTERN BOOT

My daily trifecta. It may be the beach, but it ain't cocktails and bikinis everyday. Venice can get downright chilly thanks to miss marine layer often overstaying her welcome. The key is layering: a tank for when the sun comes out, trusty broken-in denim, comfy-enough-to-walk-in cowboy boots (you can take the girl out of Texas), and a great statement coat to cinch the look.

SWEATER + SLIP DRESS + SLIP-ONS

Date night, happy hour, or girls' dinner, this is my go-to outfit. I love the feel of a slinky, figure-skimming slip. (I'm partial to ultra short or ankle-grazing.) Having a sweater on hand both ensures I'm cozy and adds dimension to the look. Because I finally learned how to ride a bike recently (no, I will not be taking questions at this time), a comfy closed-toe shoe guarantees I can pedal, walk, or if the night drags on, dance comfortably.

THE DIANA LOOK

Aka my "running errands" look. I could be on my way to a workout (but am probably just running to the Erehwon hot bar). It's sporty but polished, and if it was good enough for a princess, it's good enough for me!

Princess Diana was certainly not the first person to wear bike shorts with an oversize sweatshirt, running shoes, and high socks, but she was definitely the most memorable celebrity to do so. When I saw Taylor Swift in a similar outfit combo in New York City today, it immediately reminded me of the late royal's iconic style. 

Photographed outside Electric Lady Studios today, Swift wore a baggy Daydreamer Shania Twain Tee ($88) with bike shorts, New Balance running shoes, a Louis Vuitton bag, and FP Movement ruffled socks. This also happens to be my preferred outfit for running errands, working out, or just lounging around my house. Scroll down to see how Taylor Swift and Princess Diana styled bike shorts and shop the look for yourself. 

On Taylor Swift: Daydreamer Shania Twain Tee ($88); FP Movement Classic Ruffle Socks ($18)

Shop Bike Shorts and Running Shoes

Having written hundreds of stories covering royal fashion, I consider myself the resident royals expert here at Who What Wear. I've been chronicling the personal style of Kate Middleton, Meghan Markle, and the late Princess Diana for nearly a decade and I don't plan on stopping anytime soon—in fact, I've expanded my coverage to include TikTok too! 

I've pored over thousands of images of the British royal family and I can honestly say I've never seen the below images of Princess Diana wearing pink Converse sneakers before. From what I could find, she only wore them twice: once at a polo match in 1986 and again while visiting the British army in 1988. Over 30 years later, the shoes are as cool as ever—and still available to shop. Scroll down to see the rare photos in question and shop pink Converse sneakers for yourself. 

On Princess Diana: Converse Chuck 70 Vintage Canvas Sneakers ($90)

On Princess Diana: Converse Chuck 70 Vintage Canvas Sneakers ($90)

On Princess Diana: Converse Chuck 70 Vintage Canvas Sneakers ($90)

Shop Princess Diana's Exact Sneakers

Shop Other Converse Sneakers

Next, Anna Wintour only packed one shoe trend for all of fashion month. 

Princess Diana's fashion legacy continues to thrive. She often comes to mind when I'm watching runway shows, doing some online shopping, or scrolling through Instagram. The latest place I've spotted her style sensibility? The new arrivals section at Zara. 

In particular, I found two brand-new Zara jackets that are giving me major Princess Diana vibes: the Gold Button Textured Blazer ($99) and the Textured Houndstooth Blazer ($90). The former reminds me of a cobalt blue Chanel jacket the princess wore in 1992, while the latter made me think of the red Moschino houndstooth jacket that Di wore in 1990. Scroll down to shop both pieces. 

On Princess Diana: Chanel jacket

On Princess Diana: Moschino skirt suit 

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Next, 30 new H&M and Mango items that are Fashion with a capital F.

Whether or not hitting the ski slopes is in your future, winter temperatures are here for at least a few more months. And aside from the pros, no one did sporty fashion (before athleisure was a thing) better than Princess Diana. 

Although she was endlessly photographed in everything from ball gowns to bikinis, it is Diana's leisure looks that continue to inspire our off-duty style decades later. Case in point: her red puffer jacket. It was simple yet statement-making (you couldn't miss her on the mountain), and we love this piece not only for its place in one of the world's most iconic wardrobes but also because it is the epitome of both practical and chic. 

While Princess Diana's red ski jacket was likely of the more technical variety—she wore it to exercise, after all—we've found 11 similar styles that will suit any winter-weather leisure look from Aspen to the Alps, including a nearly identical $75 option from H&M. Keep scrolling to find your perfect red puffer to wear all winter; no ski boots required. 

Shop H&M's $75 Version

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Next, 5 Pretty Colors That Will Make Your Outfits Feel On-Trend This Winter

I love remembering Princess Diana through a fashion lens because she so clearly enjoyed expressing herself through her clothes. She was a fearless dresser and loved experimenting with the trends of the moment, but she also appreciated classic pieces.

Her style evolved significantly over the course of her tragically cut-short life. When Princess Diana emerged in the spotlight after getting engaged at only 19 years old, she favored twee sweaters, youthful overalls, and Peter Pan collars. In her 30s, she wore a lot of sharp skirt sets and tailored coats. She also gained more and more confidence as she adjusted to her post-divorce life, which was absolutely reflected in her fashion sense. Revenge dress, anyone? In homage to the late, great Princess Diana, scroll down to re-create some of her best winter outfits worn with boots. 

On a snowy day in Sandringham in 1985, Princess Diana wore a beautiful double-breasted red coat with knee-high patent boots, and her outfit is still as chic as ever in 2023. 

Princess Diana accompanied the Duchess of York on a ski trip to Switzerland, where she bundled up in an oversize scarf and cozy sweater. 

Shortly after announcing their engagement, Prince Charles and Diana Spencer posed for photos in Scotland. Her cute printed sweater and classic Hunter boots would look right at home in 2023. 

Princess Diana went casual in sweatpants and a baseball hat but polished up her look with a roomy blazer. Chic. 

Princess Diana's style remains a huge inspiration to fashion fans in the present day, and this polished, classic outfit is certainly no exception. 

Next, These Next-Gen Nepo Babies Will Be the New Bella Hadid

When it comes to fall dressing, no one has yet done it better than Princess Diana, whose sporty yet chic looks have been replicated by the best dressers countless times over the years. So it should come as no surprise that with the temperatures dipping in NYC, celebs are looking toward the late Princess of Wales for outfit inspiration. 

The first to do so in 2022 is Emily Ratajkowski, who masterfully combined cowboy boots, relaxed jeans, an '80s-style leather bomber jacket, and a baseball cap this weekend for a walk around SoHo with her son, Sylvester. While we can't know for sure if the model had Diana in mind when putting the look together, anyone who's familiar with the princess's sartorial archive will notice the similarities.

On Emily Ratajkowski: vintage Keith Haring Television Head Businessman Leather Jacket ($8019)

The outfit looks especially reminiscent of two looks of Diana's: one worn in April of 1989 to pick up her sons, Prince Harry and Prince William, from school in Notting Hill, and the other to attend an event at Guards Polo Club. For the former, she wore a tweed blazer with a white sweatsuit, brown cowboy boots, and a flat-brim blue hat. The latter saw the princess in a British Lung Foundation crew-neck, acid-wash jeans, a plaid blazer, and the same cap and boots. 

With the fifth season of The Crown now out on Netflix, Diana-inspired looks are bound to be even more popular than usual this fall. Follow EmRata's lead by re-creating the two iconic outfits below all season long. 

Shop cowboy boots and baseball caps like Princess Diana's: 

Next up: EmRata Wore a $40 Zara Skort With the Boots on Every Editor's Fall Wish List

Ever since Kate Middleton officially became a member of the Royal Family in 2011—really, even before that—the Duchess of Cambridge's style has had an undeniable influence on ours. She wears skinny jeans, we wear skinny jeans. She wears wedges, we wear wedges. It's practically a fact: Whatever Middleton wears becomes a thing. 

Given that my job is to know about trends before anyone else, I instantly perked up when I saw photo evidence of the future Queen wearing polka dots not once, not twice, but three times already this summer. After all, knowing what I know about Middleton's influence, anything she wears on three occasions will undoubtedly become a top trend of the season before long. But it wasn't until I noticed just how similar her polka-dot looks were to outfits worn by fashion's other favorite royal Princess Diana that I called it: Polka dots are about to go viral. 

On Kate Middleton: Alessandra Rich dress; Finlay Henrietta Sunglasses ($225)

WHO: Princess Diana

Middleton first debuted the print at the Big Jubilee Lunch during the Queen's Platinum Jubilee weekend in early June, choosing an electric-blue, polka dot dress by Alessandra Rich. Clearly a favorite of hers, she then wore it again just one month later at Wimbledon on Tuesday.

When compared side-by-side, the midi-length dress, which features quarter-length sleeves, a pleated skirt, and a belted waist, appears to be an homage to a similar one worn by the Princess of Wales in 1989 during a trip to Kuwait. Princess Diana's dress likewise featured a pleated skirt and white polka dots, though hers included a white collar and matching, oversize buttons. (It was the '80s, after all.)

On Kate Middleton: Alessandra Rich dress; Sally-Ann Provan hat

WHO: Princess Diana

In between, the Duchess of Cambridge attended the 2022 Royal Ascot, where she wore an almost identical outfit to one worn by Princess Diana at the same event in 1988: a white polka-dot dress with pearl jewelry and, of course, a wide-brim hat. Middleton specifically chose an Alessandra Rich dress with chocolate-brown spots and a matching Sally-Ann Provan hat. Her late mother-in-law's look only differed in that her '80s-era look was black-and-white and paired with a gold watch. 

Given how much power the two women have over our sartorial choices, it'd be a mistake not to get a head start on what will assuredly become a major trend this summer. Keep scrolling to shop the royal-approved print.

Shop the Polka-Dot Trend

Coming Up: Kate Middleton Just Wore the Gorgeous Color That's Trending at Zara and Mango

Who's ready for the 2022 Met Gala? Before we get to the first Monday in May, let's take a second to revisit one of the event's most memorable moments of all time: Princess Diana's one and only visit in 1996. The royal had already established herself as a fashion icon, so no doubt fans were excited to see her grace the steps of the Metropolitan Museum of Art.

For the occasion, Princess Diana went with a lingerie-inspired John Galliano for Dior satin slip dress with lace trim—a classic item that's still just as stylish in 2022 as it was back then. Diana wore her gown with a Lady Dior bag, a stunning statement pearl choker necklace—another '90s trend that's back with a vengeance—and sapphire earrings that have since been passed down to Kate Middleton. There's no doubt that Princess Diana's fashionable, charitable legacy lives on to this day. Scroll down to revisit what Princess Diana wore to the Met Gala in 1996, and shop the trend. 

On Princess Diana: John Galliano for Dior dress; Lady Dior handbag

Shop Satin and Silk Slip Dresses With Lace Trim

Next, the 2022 Met Gala theme, explained—and six trends to expect on the red carpet.

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

While browsing through fall new arrivals, I couldn't help but notice a few sporty sweaters that look incredibly familiar. Then it hit me: None other than Princess Diana had the style in her stellar sweater collection. Varsity sweaters are certainly nothing new, but with sports like tennis and pickleball being fashion favorites right now, I'm not surprised the prep-adjacent trend is all over the market. Plus, after all the elegant looks from Wimbledon, I'm anticipating more people incorporating preppy knitwear into their 2025 fall wardrobes.

From a $20 option at H&M to an $810 Wales Bonner sweater at the top of my wish list, I've rounded up the best varsity sweaters money can buy right now. When you come across a royalty-approved trend at an under-$100 price point, you have to give it a look. But also, if there's anything that Princess Diana's style taught us, it's that the pieces she wore will never be quite out of style. So if you're willing to splurge on the pricier ones below, I support it. Keep scrolling to find your sweater pick for the season.

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

Shop Varsity Sweaters

I recently asked my friends what four famous figures they’d choose to be on their personal Mount Rushmore and the results were not all that surprising. Their choices were so consistent with who they are as people that the exercise felt like a personality recipe that when followed, would *ding* and pop my friend out of the toaster. 

When it was my turn to answer the question, I was shocked at how much my top inspirations included aesthetic considerations—each of my four had a distinct personal style. After questioning my vanity for a good two minutes, I now rest assured that this isn't a coincidence and is actually borne from true alignment where purpose and values align in every sense, even stylistically. This, my friends, is the pinnacle of success. 

I’m here today to share my fashion Mount Rushmore with you all and, of course, re-create some of their best looks. The four women below not only look good, but they each also follow a consistent process that ensures every look feels like them. While I like to think my personal style stems from my own unique process, these women constantly inspire me and introduce new ways of looking at things. Keep scrolling to see who I’ve chosen along with some amazing pieces I’m certain they would wear today. Who’s on your fashion Mount Rushmore?

Rihanna

Everybody loves RiRi. Where many celebrities today have stylists and creative directors guiding their image decisions, we can all tell that Rihanna is the one driving the boat. She has the sauce and there is no denying it. I love that she is always trying new things and mixing different inspirations to create something that is uniquely her. Take for example the below outfit which places streetwear inspirations alongside Chanel and pearls. Chef's kiss.

I went with a bikini top and fur coat because why not? The combination of the two feels very much "I do what I want" aka very Rihanna. 

Shop similar pieces:

Princess Diana

As a kid, I always looked up to Princess Diana's impeccable and classic style. Her ability to push the bounds of her role in the royal family and fashion both make her an icon for the ages. She's pictured below for the first time after her husband publically admitted to adultery wearing a little black number now referred to as the "revenge dress." Again, the story matches the vibes matches the outfit—it's all about alignment.

This dress by Nana Jacqueline is equal parts refined and equal parts sexy. A string of pearls and rhinestones wraps around the waist showing the perfect amount of skin and leaves the rest to the imagination.

I paired the modern-day equivalent of the Revenge Dress with rhinestone earrings from Nana Jacqueline that form the shape of a heart. 

Shop similar pieces:

Solange

Solange has meticulously curated her stylistic presence to match the vibes of her musical projects, which has really pushed the message even further. She tends to go for more avant-garde designers and silhouettes that help us reimagine the future without bounds. It's rare to see mainstream artists approach fashion so fearlessly and bring to the forefront ideas that usually don't make it into the spotlight. 

This hoodie dress by Armande is so sick that I knew I had to try it on for the Solange look. It's made from 100% silk that feels so nice against the body and drapes beautifully. I paired it with a cowboy hat and boots because we all know Solange doesn't play about where she's from (Houston, Texas). That's actually one of the things I appreciate about her most—she is true to the culture that makes her who she is today.

This Solange look also features pieces from Armande's Demystified collection, which is purposefully all black to showcase the depth of blackness and allows us to focus on the details. I am wearing the satin organza trousers and the mesh gloves, both of which give an enviable air of self-assuredness. I love how these pieces are understated yet eye-catching, and I feel like Solange would appreciate them too.

Shop similar pieces:

Paloma Elsesser

The newest kid on my Mount Rushmore block is none other than fashion's favorite girl, Paloma Elsesser. When I tell you I love every single thing she wears, I'm not exaggerating. Similar to Rih, she is constantly reevaluating what styles work well together, taps into trends without looking overly trendy, and oozes with cool-girl confidence while doing it. I'm excited to see how her style evolves over the years and will undoubtedly be paying attention to the playbook she's creating.

As you can see, this look can be re-created in a million different ways, and that's a key lesson in personal style. I've found that all the most stylish women know the silhouettes that look good on them. Another variation of this look that Paloma always gravitates to is the small-top–and–baggy-pants look. 

Shop similar pieces:

Next: Buh-Bye, Cutouts and Hello, Negative Space—6 Ways to Wear the Trend.

Princess Diana's legacy continues to live on in numerous ways, including via several TV and film portrayals and, most importantly, through her children and grandchildren. Her daughters-in-law, too, have a special opportunity to carry a piece of Diana with them by way of jewelry.

Kate Middleton and Meghan Markle have both inherited several pieces of jewelry from the late icon's personal collection, and it's bittersweet to see the precious pieces back in the spotlight. Of course, you already know that the Duchess of Cambridge's sapphire engagement ring once belonged to Diana, but her collection also includes plenty of other memorable pieces. Scroll down to revisit Princess Diana's jewelry and shop similar pieces. 

1. Butterfly Earrings

Princess Diana wore her diamond-embellished butterfly earrings on numerous occasions, including a visit to Canada in May 1986, as shown here. 

Meghan debuted the same earrings on her royal visit to Australia with Prince Harry in 2018. It was the first time she was seen in public since announcing that she was expecting baby Archie. 

2. Diamond Tennis Bracelet

Along with her trendier pieces, Princess Diana loved wearing her classic diamond tennis bracelet. Here, she wore the bracelet to a gala benefiting the Red Cross in Washington, D.C., in June 1997. 

Meghan has worn Diana's tennis bracelet several times, most recently at the Salute to Freedom Gala in November 2021. She paired it with a gold Cartier Love bracelet. 

3. Diamond-and-Pearl Earrings

For fancy occasions, Princess Diana often paired a tiara with these earrings. 

The duchess wore Diana's earrings to a red carpet event back in 2013. 

4. Three-Strand Pearl Bracelet

Princess Diana brought along her three-strand pearl bracelet on her trip to Hong Kong in November 1989.

Kate followed suit and brought the same pearl bracelet along on an international trip—specifically to Germany in 2017. 

5. Pearl Earrings

Collingwood the Jeweller gifted these pearl earrings to Princess Diana for her wedding. 

The Duchess of Cambridge wears these earrings frequently. Here, she wears them for a solemn occasion: a Remembrance Sunday service in November 2021. 

6. Aquamarine Ring

Princess Diana's enormous aquamarine ring made several appearances, including at this event in June 1997. 

Meghan famously flashed the huge ring as she was on her way to her wedding reception in 2018. 

7. Sapphire Engagement Ring

Arguably the most famous piece of jewelry in existence, Princess Diana's 12-carat sapphire engagement ring now belongs to Kate. 

The Duchess of Cambridge never takes off her special engagement ring inherited from Diana. 

8. Sapphire Earrings

To complement her blue engagement ring, Princess Diana owned several other pieces of sapphire jewelry, as shown here in 1991. 

Kate customized Diana's earrings and only used one stone per earring. 

Next, Jennifer Aniston and J.Lo both wore the denim trend I'm replacing skinnies with. 

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. 

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, jewelry, 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. 

If you know fashion, you know that Princess Diana has been remembered for her iconic style. So iconic that many Gen Zers, who hadn't been around to see the life of Princess Di, are fascinated with her style and consider her an icon. Personally, I have always been inspired by the way she dressed. From laid-back outfits to her more "royal" moments, every look she wore encompassed a hint of casual classiness that I just adore.

While Princess Diana wore many iconic outfits I've re-created myself, I thought about what items currently on the market have that cool "people's princess" vibe. After using some of Diana's old outfits as a guide, I got to searching for pieces that had the Princess of Wales' essence and ended up with 30 picks that I think nailed it. 

If Lady Di is also constantly on your mood board, you're going to want to take a look at these…

Shop More Princess Diana–Inspired Picks