More so than ever before has the concept of taste been mired in discourse. To me, however, the notion of possessing great taste is akin to having enough life experience to distinguish between something that’s trending, passé, or pastiche, and to know the precise contexts that suit each best. So, when it comes to fashion, that’s why I always look to those slightly older than myself for inspiration.

This summer, specifically, I’m turning to a set of over-50s style savants for guidance on how to dress, using their personal sartorial philosophies as a lens to filter out anything that could easily date, appear trite or simply convey that I’m replicating some niche aesthetic espoused as “in” on the internet.

As far as seasons go, those over 50 really do summer trends best. In part because they’ve had close to five decades to cultivate and hone a wardrobe that complements them, but also because the warm weather invites a more minimalistic approach that’s more in keeping with how many quinquagenarians like to dress.

Whilst many Gen Zers like myself often find ourselves asking tedious questions when putting together an ensemble to ensure what we wear reflects our self-expression—like whether this piece of clothing is truly “me”—those over 50 tend to be less pensive. With more impulsivity and spontaneity, their looks are instilled with a sense of quiet confidence and effortless elegance.

Still, if you’re looking for practical tips from this cohort, there’s a lot to be gleaned. The primary lesson is to never overlook the power of a solid basic, which is something the likes of Cindy Crawford and Jennifer Aniston have proved time and time again with their adoration for a pair of sturdy denim jeans and crisp white t-shirts.

Because, ultimately, the bona fide way to express that you have good taste is to study the masters, learn their techniques and apply what resonates with you most. Miuccia Prada said it best when she said, “Study, study, study. Learn, watch movies, look at art, read literature.” Or, in this case, scroll through for a comprehensive breakdown of the 6 key summer trends those over 50s will be wearing all season long.

6 Chic Over 50s Summer 2026 Fashion Trends

1. White Skirts

Style Notes: White skirts have been a mainstay in summer for nearly a century. Though the calf-grazing length can sometimes feel a bit matronly—perhaps due to its connotations with nurse uniforms, which is a trope Prada reinforced in its autumn/winter 2023 collection—stars like Demi Moore and former J.CREW creative director, Jenna Lyons is proving just how versatile the trend is this season. Pair with everything from a ribbed tank top and suede ballet flats to structured tailoring and oversized sunglasses.

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2. Dark Wash Jeans

Style Notes: Though the natural inclination when the temperature rises is to wear lighter hues that match this climatic mood, stars like Tracee Ellis Ross are making a case for subverting the norm. Indeed, opting for dark-wash jeans rendered in rich-looking indigo shade, like the Pattern Beauty founder has for Dior’s recent Cruise 2027 collection presentation in Los Angeles, adds a depth and sense of intrigue to your look. Plus, for moments when monochrome, all-black dressing starts to wane, this colour scheme offers a point of difference, while still retaining the same qualities.

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3. Royal Purple Hues

Style Notes: In a similar vein, royal purple palettes have become one of the most commanding colours of summer. This makes sense considering it’s the scion of two of the biggest shades of the year (tomato red and cobalt blue), but for those after something a little more enigmatic while still capturing the trend cycle, this colour does it all. Already traipsing down the runway, from magnetic plums at Prada to vibrant violets at Balenciaga, follow in suit through sheer touches, lightweight knits and functional base layers.

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4. Oversized Shirting

Style Notes: The button-down shirt is fashion’s workhorse. Dependable, practical and often overlooked, this is a staple that serves as the canvas for so many looks, whether it be something more proper for office settings or deliciously languid for holidays. This summer, the stylish over-50s are thrusting it back into the spotlight. Perennially appealing with a loose-cut insouciance, style with stovepipe jeans and slingbacks or that white skirt you picked up earlier in the article.

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5. Classic LBDs

Style Notes: To have great taste is to invest in something that will only get better with time. Such is the case with the classic little black dress. Though not specifically a trend, given its universal appeal and timeless status, it is a silhouette that’s currently garnering interest again. Blame it on Mattheiu Blazy turning our attention back to Gabrielle Chanel and the origins of the house, but this renewed attraction only serves to prove how enduring and chic this style is. Wear at long al fresco lunches, casual days perusing vintage boutiques or evening soirees.

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6. Basket Bags

Style Notes: With age comes wisdom, like the knowledge that sometimes investing in a humble basket bag is just as sufficient as purchasing the latest designer bag. At least, that is the case for some of the most stylish over-50s, choosing to go down the path paved by Jane Birkin in the ‘60s. More subtle and refined, be it raffia or woven leather, these basket bags add a charming touch and Côte d'Azur breeziness that’s so essential for summer.

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As the first real stretch of summer sunshine settles in, Jennifer Aniston has officially swapped out her signature white trainers for a warm-weather staple she’s relied on for decades: a pair of sleek black flip-flops.

A constant in her on and off-duty wardrobe, these pared-back sandals are her go-to the moment temperatures begin to climb, and this summer will be no exception. Stepping out between filming scenes for season five of The Morning Show, Aniston once again reached for the minimalist style to carry her through the heat with ease.

Opting for a simple, refined design in a timeless black hue, the understated sandals paired naturally with her floor-skimming teal dress. But, of course, this isn’t the first time Aniston has championed the look. She’s been styling flip-flops since the late '90s, yet they feel just as relevant today. Unfussy, versatile and immune to the whims of passing trends, this low-key shoe is bound to be called up for many more summers to come.

Just as chic in 1999 as it is in 2026, keep scrolling to discover and shop the best pairs to wear now.

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There’s never been a better time to be a product of the ‘90s than right now. Carolyn Bessette Kennedy’s subtly sophisticated ensembles are back in the spotlight, Posh Spice is making her trademark sharp tailoring more accessible than ever through her collaboration with high-street giant Gap, jelly sandals have become the acme of luxury, and Practical Magic is heading back to the big screen with a highly anticipated witchy sequel.

Of course, that’s not even mentioning the breadth of sartorial moments that are staging a comeback. From pencil skirts seen all over the Chanel runway and in the new season collections of defiantly minimal brands like St. Agni to the return of Galliano-for-Dior-esque lace-trim slip dresses, it seems that everything old is new again.

Still, if there was one fashion category that was making the biggest mark this spring, it would certainly have to be denim. Specifically, ‘90s jeans trends are making a roaring return this year, with some of the biggest silhouettes being the ones that were most popular close to three decades ago.

Leading the pack is none other than stovepipe jeans. Sharp, polished and cut close to the body, this elongating trouser style was a favourite of supermodels off duty like Cindy Crawford and Christy Turlington and has now been adopted by contemporary style savants, including Alexa Chung and Kendall Jenner.

Their appeal lies in their innate elegance, architectural nature and versatility in styling. Slip into a pair, and you’ll find any spring jacket—though bonus points are awarded if the piece is more ornate, like the floral embroidered and opera-inspired styles seen at Valentino, Conner Ives and Viktor Gichev—appears more elevated than ever.

Elsewhere across fashion capitals, perennially functional bootcut jeans is piquing interest. Of course, the most obvious companion to your favourite pair of knee-high, heeled leather boots, but they also make a worthy partner to sleek ballet pumps, heeled sandals and satin trousers. And when it’s a style that’s been endorsed by the likes of Kate Moss and Gwyneth Paltrow for years—and now a cornerstone of Bella Hadid and Hailey Bieber’s wardrobe—what’s not to like?

The most surprising ‘90s jeans trend to come back this spring, however, would have to be cuffed jeans. With an exposed hem and ankle-grazing cut, this style is actually the most democratic of the bunch, given its ability to transform any existing pair of jeans into this fashion-forward style, all with a simple fold.

Still, there are so many vintage-inspired shapes to choose from. Better yet, the market is currently saturated with modern versions of these archival styles, meaning that you don’t have to go hunting down Brick Lane’s boutiques for a pair of old school Levi’s to fill this gap. Below, Who What Wear rounds up the 5 key ‘90s jeans trends that are spearheading spring 2026, the styling differences between now and then and the best updated pieces to shop.

5 90s Jeans Trends Spring 2026

1. Bootcut Jeans

Style Notes: Despite originating in the rodeo, these days, you’re more likely to find bootcut jeans in high-end restaurants. With a soft flare and extra sumptuous to the touch, this silhouette benefits from its ability to be dressed up and down with aplomb. Complementary to longline coats, cropped jackets, knitted sweaters and even humble white t-shirts alike, the sleek widening effect will help any outfit appear both considered and casual.

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2. Mid-Rise Jeans

Style Notes: If the ‘00s had low-rise, almost-bumster-level jeans and the ‘10s had ultra high-rises that rode up to the bottom of your ribcage, then both the ‘90s and now have mid-rise shapes. Consider this like the Goldilocks of jeans—a placid, low-effort and easy-going style that serves as a happy medium between both these extremes. In fact, you’ll find that the most sought-after denim styles of this decade are actually mid-rises, including Khaite’s beloved Danielle jeans and Agolde’s ‘90s pinch waist style. (How very apt!)

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3. Dark Wash Jeans

Style Notes: When it comes to ‘90s jeans trends, you must remember that it’s not always about the specific cut. Indeed, sometimes it comes down to the colour you wear. And if you were to flick through shots of memorable outfits from the period, you’ll often find tastemakers of the time gravitating towards dark washes. From deep blues to saturated indigos, the rich-looking hue can’t help but look far more premium than its lighter counterparts, leading to the wearer coming across as more thoughtful and chic.

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4. Stovepipe Jeans

Style Notes: If there’s one denim trend that will continue to dominate, it’s stovepipe jeans. A successor to the cigarette jeans that defined the early part of the decade, this style sits a little more loosely through the thigh and finishes with a punctuated and polished clean-cut hem. Style with mock croc court shoes, simple slingbacks or even a simple ballet flat. Regardless of the choice, the stovepipe shape will suit anything it’s styled with.

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5. Cuffed Jeans

Style Notes: From Lila Moss to Emily Ratajkowski and Michaela Coel, the most refined dressers of this day and age have taken to intentionally cuffing their jeans. Though this was a technique embraced by Jennifer Aniston all those years ago, the effect remains the same, leading to an outfit brimming with visual contrast, thanks to the barely-there two-toned effect.

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I’ve been writing about Jennifer Aniston’s style for years, and one thing I’ve come to realise is that she’s at her chicest when the temperature starts to rise. As heavy boots and bulky puffers fall away and her wardrobe shifts towards a streamlined rotation of lightweight tops, well-cut jeans and wearable footwear, is when the actor's outfits really shine.

Looking to channel some of that ease, I’ve pinpointed the key pieces she returns to year after year. From the pretty top to the perfect jeans and the chic shoes, read on to discover Jennifer's favourite spring trends below.

3 Spring Trends Jennifer Aniston Always Comes Back To

1. Flip Flops

Style Notes: I’m calling it—sandal season has arrived, and the chicest pair you can slip into right now is a classic set of flip flops. Minimal, unfussy and versatile, they work with far more than you might expect. Jennifer styled hers with light tan jeans for a spring-ready look that felt polished without trying too hard.

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2. Tailored Vest

Style Notes: A holdover from the '90s, the tailored vest remains a cornerstone of Jennifer Aniston’s wardrobe. Sharper than a basic tee but more relaxed than a blouse, it's an elevated alternative that fashion people return to time and again.

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3. Cropped Jeans

Style Notes: Instead of stovepipe or baggy styles, Jennifer consistently comes back to cropped denim. Fresh and inherently spring-ready, this silhouette brings a lightness to her outfits that always wears well with flats. This season, I’ll be taking cues from her and styling mine with crisp white trainers.

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Given the fact that one of the most memorable performances given by Jennifer Aniston involves flying —you know, the one from Friends where Rachel shows up at Ross’s doorstep when she’s supposed to be en route to Paris to reveal she “got off the plane” to be with him—it should come as no surprise that she’s no stranger to a chic airport outfit. What might pique your interest, however, is the footwear she chooses to travel in.

Despite owning a private jet, the actress’s red-eye attire is still quite consistent with her preference for timeless tailoring and pared- back basics. You’ll often see her arriving at L.A.X wearing a simple pair of khaki trousers, a crisp white t-shirt and bundled underneath a chic scarf, which isn’t at all unusual for the ensembles you’d spot in a departures hall. Yet, in spite of the minimalistic silhouette, the 57-year-old will always complete her look with some sort of balmy shoe.

Ask anyone who travels frequently, and they’ll tell you that anything open-toe is forbidden. But for Aniston, a sunny pair of wedge espadrilles, breezy flip-flops, or even a casual, low-profile trainer is the perfect choice. (I don’t even want to begin speculating what happens if she’s asked to remove her shoes at security check!)

Indeed, from the ‘90s to now, the Emmy Award winner has always called up styles that are more or less unconventional for their settings. But with the Euro Summer fast approaching and fashion’s new mood of unbridled joy, why not bring a sense of playfulness to your travel look by wearing sandals or slimline trainers for take off? Whether you have a holiday on the horizon or are just dreaming of an escape, scroll on through for the three shoe trends Jennifer Aniston always relies on to make her airport outfits a little brighter.

3 Shoe Trends Jennifer Aniston Always Wears to the Airport

1. Wedge Espadrille

Style Notes: You wouldn’t give this shoe a second look if you noticed them poking out of the sand on some tranquil beach along the Côte d'Azur or Italian Riviera, but sporting espadrilles to Heathrow Terminal 5 feels entirely wrong. Well, at least that was the case before Jennifer Aniston made such a compelling case for trying this shoe choice out.

Personally, I think this is no different to that iconic photo of Ashley Olsen wearing a raffia cowboy hat and ludicrously capacious carry-on bag to the airport in Cabo San Lucas all the way back in 2004. Because who said your vacation had to start only once you touched down?

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2. Flip-Flops

Style Notes: A slightly more palatable option, but one that’s still polarising nonetheless. However, when you consider Aniston’s most iconic off-duty looks—wearing a pair of calf-grazing Lucozade orange cargo pants with platform thongs in the late ‘90s—you’ll realise just how staunchly supportive she’s been to the trend. Because before they were adopted by adherents of The Row and rendered in jelly format like the viral Christopher Esber ones, Aniston was there first.

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3. Low-Profile Trainers

Style Notes: Of course, they can’t all be polarising. Still as fluid and relaxed as her preferred sandals, this functional choice adds a more dynamic element to her look, rooting them in a practical and casual ease. Of course, keeping a light tread, these sleeker shapes soften the overall ensemble and lead to a more polished silhouette, which is perfect for moments when you might be testing the limits of your EasyJet weight limit…

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I’ve been admiring Jennifer Aniston’s style for as long as I can remember. So whenever she steps out—especially in jeans—you can be sure I’m paying close attention.

Denim forms the backbone of my own wardrobe. I reach for jeans at least five days a week (in fact, I’m sitting in my favourite pair as I type), so I’m always ready to be inspired by a fresh take on the classic. Needless to say, when I spotted Aniston out in New York this week wearing a chic silhouette, I took note.

Sidestepping the season’s ubiquitous stovepipe styles—and long past the skinny jeans she once favoured—Aniston opted instead for a slim-cut pair that gently puddled around her ankles. The subtle pooling gave her look a relaxed, insouciant edge that, though it remained streamlined through the leg, offered just enough length to create that coveted slouch.

Of course, puddle jeans live or die by their shoe pairing. Too flat, and the hem risks dragging; too delicate, and it disappears entirely beneath the fabric. Aniston’s solution? A thick-soled black heeled boot. The added height accommodated the full sweep of the denim, while the sturdy silhouette anchored the look and lent a sharper finish. Where trainers might have felt overly languid and Mary Janes lost under the excess fabric, her boots made for the perfect pairing.

Styled with a substantial olive-green coat draped over her arm and lightly tinted sunglasses framing her face, the outfit felt perfectly attuned to this in-between season.

As ever, I’m taking notes. If you’re feeling inspired too, keep scrolling to discover the chicest puddle jeans and black heeled boots to recreate the look.

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Above all else, I’m a jeans person. While I love sharp tailoring and playful skirts on others, my own daily uniform will always prioritise denim. I take the subject seriously, borderline devotionally, so I’m constantly tracking emerging jeans trends and bookmarking styling inspiration. And when it comes to denim muses, Jennifer Aniston reigns supreme.

Whether it was 1996 or 2026, the actor has always made a compelling case for the humble pair of jeans. Her ’90s off-duty style in particular remains a one of my favourite sources of inspiration.

With a new year ahead and a renewed desire to invest in the hardest-working corner of my wardrobe, I’ve been delving into the archives to revisit the ’90s Jennifer Aniston jeans trends that still hold up today. From relaxed silhouettes to flattering cuts, these are the denim styles that feel just as chic now as they did three decades ago.

Scroll on to discover the Jennifer Aniston–approved jeans trends I’ll still be wearing in 2026.

Discover Jennifer Aniston's '90s Jeans Trends

1. Stove Pipe Jeans

Style Notes: Stove pipe jeans are enjoying a resurgence in 2026, and if the ’90s taught us anything, it’s that this is one of the chicest silhouettes you can wear. Jennifer’s original formula, sleek sleeveless tops paired with heeled boots, still feels entirely relevant today. For now, layer yours with a chunky knit while winter lingers; come summer, follow Aniston’s lead and swap in a pared-back sleeveless top for a polished finish.

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2. Bootcut Jeans

Style Notes: Set for a full-scale revival this year, bootcut jeans are finally breaking back into the mainstream. A long-time advocate of the silhouette, Jennifer proved in the late ’90s that bootcuts never deserved to fall out of favour. Styled with a heeled boot, they subtly elongate the leg while balancing bulkier winter layers. There’s a hint of retro appeal, but they feel more elevated than your average straight-leg—making them a strong contender for one of 2026’s biggest denim trends.

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3. Cuffed Relaxed Jeans

Style Notes: Cuffed jeans may have surged in popularity only a few seasons ago, but Jennifer Aniston was wearing them long before they were cool (again). The turned-up hem lends a nonchalant edge, while the cropped length brings a lightness that full-length jeans often lack. Easy, relaxed and always cool, this is the kind of styling trick that proves why her ’90s denim wardrobe still resonates today.

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White trainers may be a wardrobe pillar, but after seasons of experimenting with colourful pairs, their gleaming appeal has softened slightly. Still undeniably classic, making them feel fresh for 2026 is all about the styling—pair them with the wrong trousers or skirt and suddenly your look is thrown back a decade. Thankfully, some timely inspiration has just landed, courtesy of my perennial style muse, Jennifer Aniston.

Stepping out this week, Jennifer reaffirmed the enduring relevance of the white trainer, styling a crisp pair with a decisively modern jean. Sidestepping skinny silhouettes that would have instantly dated the look—and resisting the trending bootcut that risks overwhelming a flat shoe—she opted instead for wide-leg, light-wash denim, creating a relaxed yet polished outfit that feels perfectly calibrated for spring 2026.

Lighter and more optimistic than the indigo shades that dominated winter, pale blue denim creates a harmonious pairing with bright white trainers. Rather than emphasising their starkness, it highlights their softness and luminosity, giving the entire outfit a fresher, more effortless feel.

To finish, Aniston layered up for the lingering chill with a longline khaki puffer coat. The muted, earthy tone grounded the look while sitting well alongside the lighter denim-and-white combination.

Officially inspired to give my white trainers a little more airtime, scroll on to discover and shop the light-wash jeans and crisp white trainers worth investing in now.

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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 it comes to spotting the styling tricks that really matter, I tend to look less to the runways and more to the celebrities whose outfits consistently resonate. And funnily enough, two of my biggest style muses happen to share the same first name: Jennifer Aniston and Jennifer Lawrence. Whether by coincidence or fate, both Jennifers consistently achieve the kind of effortless looks that shape the way I get dressed.

My own style leans minimal with a ’90s undercurrent, so it’s no surprise that Aniston’s Friends-era wardrobe often informs my day-to-day outfits. But when I want to push that aesthetic into 2025, Lawrence is the Jennifer I turn to. So when I spotted a recent look from her that instantly reminded me of vintage Aniston, I knew I’d found a styling trick worth noting.

This week, Lawrence was photographed in relaxed, low-rise jeans sitting casually on her hips, finished with a sleek black leather belt. It’s not a groundbreaking move, but it did feel striking—largely because belts have quietly disappeared from denim outfits in recent decades. While fashion insiders have been pairing jeans with bare waistbands, Aniston was once devoted to the belt, wearing it as her signature finishing touch throughout the ’90s.

A clean leather belt adds polish, structure and a sense of intention to even the most pared-back jeans-and-tee look. It’s a subtle styling tweak that instantly lifts an outfit, and it's also something I spotted over and over again among the street style set at New York Fashion Week this September.

Best of all, this is a trend that costs nothing extra. Most of us already own a belt or two, and looping one through your jeans delivers a Jennifer-approved outfit formula that’s stood the test of time. Pair it with your favourite tee or crisp shirt, and you’ve got a look that works as well in 2025 as it did in the ’90s.

If you’re in need of a refresh, keep scrolling for my edit of the best jeans and belts to re-create the look.

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When I’m pulling together a simple outfit—say, jeans and a tank top—my instinct is usually to reach for shoes that add a little polish, like a sleek kitten heel or an interesting mule.

Trainers, however, are rarely my first choice. Too often, their casual energy feels a little boring, and unless the design really stands out, they don’t always inspire me. That said, there are a few trainer updates that can work wonders, and embracing them in the season’s favourite shades is one of the easiest ways to elevate a look. So, when I spotted Jennifer Aniston styling her classic jeans-and-vest combo with a pair of Adidas Samba Trainers (£95) with fiery red accents, I knew she’d found the perfect pairing.

With their trendy colouring but streamlined design, the trainers added a modern edge without trying too hard. The subtle hit of red picked up on one of autumn's favourite colour trends, instantly freshening her pared-back outfit whilst injecting a 2025 feel into the simple formula.

Jennifer kept the rest of her look low-key, throwing a jumper casually over her shoulders and finishing with aviator sunglasses, achieving that relaxed, wearable vibe she does so well. If you’re also tempted to give your basics a refresh, a pair of red trainers just might be the easiest way.

Below, I’ve rounded up the best styles to shop now.

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I've always felt that September shifts the styling mood more than any other month.

As the new-season energy kicks in, capsule wardrobes often follow suit, mine included. Without even meaning to, I’ve been trading in jeans for tailored trousers, tees for button-downs and trainers for something sleeker as I work towards channelling a more polished silhouette. Whilst easing into this new rhythm, I’ve been on the lookout for styling inspiration to maximise my early-autumn looks. And this morning, Jennifer Aniston delivered this in spades, stepping out in an autumn shoe trend that elevates tailored trousers in a '90s-minimalist kind of way.

Styling her long black tailored trousers with pointed-toe heels in glossy black leather, the shape of the shoe made her legs look like they go on and on (and on), whilst the sleek heel added a certain poise that flats can never quite match. A reliable pairing that felt sharp and polished but not overly serious, Aniston added a V-neck waistcoat, delicate jewels and a pair of tinted brown aviators, crafting an elegant outfit that would easily see you through the season. Dare I say, it’s the perfect September ensemble: streamlined, easy and inherently chic.

Not the first time we've seen her step out in this inherently elegant formula, it's safe to say that the pairing looks just as chic now as it did in 1999.

Below, shop the best black trousers and pointed-toe heels to re-create Aniston’s outfit below.

Shop Pointed-Toe Heels and Black Trousers

Jeans are, by far, the most worn wardrobe item in my closet and always will be. I love light-wash and dark-wash pairs equally and never shy away from the occasional white or black version. For me and many others, these, dare I say, basic jeans options will never be out. However, there are more current denim trends to explore, and they shouldn't be overlooked just because the classic styles continue to be great. One trend that's particularly buzzy for autumn 2025 is khaki denim, and brands like Agolde, Citizens of Humanity, and Free People are all jumping on board. You know who else is hyped about the khaki-denim trend? Jennifer Aniston.

The Friends star was spotted leaving the Greenwich Hotel in Tribeca alongside Jim Curtis wearing a simple yet chic outfit for a day in New York City. It included a black tank top, a tan hat, brown Tkees flip-flops, and a pair of cropped, slim-fit khaki jeans. She finished off the ensemble with a few necklaces, a watch, and a pair of oversize aviator-style sunglasses.

The denim colour has been bubbling up for a while now and has mostly been styled with either black or white tops and Aniston's same sandal choice. Though, you could easily dress it up with classic mules or slingbacks for a night out. Add a black belt for added intention, or do like the It girls in 2025 and tie a silk scarf around your waist to add some colour. Given that khaki is such a neutral shade, the styling possibilities with this denim option are truly endless, and with so many fashion people wearing it right now, there's also an abundance of outfit inspiration to help you introduce it into your fall 2025 wardrobe.

Keep scrolling to shop the best khaki jeans for autumn 2025 and beyond.

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Jennifer Aniston is nothing if not consistent. From her iconic ’90s layered haircut to her reliable capsule wardrobe, the actor has always remained loyal to her own blend of laid-back dressing and style. Her latest outfit is no exception, and it reminded me why I always come back to her when I'm in need of casual outfit inspiration. Cue an ensemble featuring a black slip dress and her most worn pair of shoes—flip-flops.

While a black slip dress can easily veer into formal territory, Aniston gave hers an unmistakably cool, L.A.-coded spin with the shoe choice she’s been loyal to since the Friends days—simple, elevated black flip flops. And no, not the chunky or embellished styles that have been vying for our collective attention this summer. I’m talking about the truly understated, barely-there kind that make everything you wear with them look a little more relaxed (and a lot more effortless).

I’ve always appreciated how Aniston makes a classic feel current without leaning into trends. The look is polished, yes, but also totally wearable—perfect for, well, really any occasion that doesn't involve someone walking down the aisle. Though I imagine with a metallic bag and some bold earrings, Aniston would have made this look work for such an occasion—that's just how "her" it is.

It’s a quiet reminder (and one I’m personally taking note of) that some of the best warm-weather outfits come down to the simplest pairings: a great black dress and the flip-flops you’ve probably had at the back of your wardrobe for years. That said, scroll on to shop my edit of both below, in case you fancy a refresh in either department.

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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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Even though I don't travel as much as I'd like to, I still have a healthy number of stamps on my passport. My most frequent international destination? Copenhagen, where I've been attending the city's biannual fashion week for many years. Whenever I find myself people-watching at terminals in Los Angeles, Copenhagen, or any other airport around the world, there's one denim trend I see on scores of stylish people: baggy wide-leg jeans.

Jennifer Aniston clearly got the memo because she was recently photographed breezing through LAX in the comfiest, coolest pair of baggy jeans, and I can't help but think this is further proof that travellers everywhere are ditching skinny jeans in favour of looser silhouettes. Aniston paired her roomy denim with a fedora, a classic white tank top, and the shoe trend she's been wearing consistently since the '90s: flip-flops.

Her travel outfit makes total sense: When you're hopping on a long-haul flight or navigating a crowded security line, comfort is non-negotiable—and baggy jeans deliver. Think of them as the airport equivalent of a first-class upgrade for your legs. Stiff, tight jeans, on the other hand? Wearing those is like being stuck next to the bathroom in the back row. Scroll on to see Aniston's full travel look and shop similar styles.

Re-Create Jennifer Aniston's Airport Outfit

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I'll admit it—the trend cycle moves fast. But I’ll stand by this: not every trend that comes "in" is destined to be dragged "out" again. Case in point? The enduring jeans-and-sandals pairing Jennifer Aniston has been wearing since 2004.

Transcending fleeting fashion moments, Aniston has long understood the lasting appeal of a flip-flop-and-jeans combo. Styling the effortless look just this week, she stepped out in baggy mid-wash jeans, a sleeveless checked top, an elegant tan hat and, of course, a relaxed pair of flip-flops.

This certainly isn’t the first time we’ve seen her lean into the throw-on formula. In fact, the moment I spotted the new image this morning, I couldn’t help but recall a strikingly similar look from November 2004. Same relaxed blue jeans, same easy thong sandals—proof that some outfits really do stand the test of time.

The enduring appeal of this classic combination lies in its simplicity: denim—a wardrobe hero that, although styles and cuts may ebb and flow in popularity, will never leave our repertoire—meets the effortless appeal of a slip-on flip-flop. The gold-star standard in easy-going, chic styling, this tried-and-true combination will continue to deliver year after year.

Read on to shop my edit of the best jeans and flip-flops below.

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I never used to think of Jennifer Aniston as a style inspiration outside of her iconic Rachel Green looks from Friends, but lately, she's been making waves in L.A. with some effortlessly cool outfits that have caught my eye. What’s striking about them is their simplicity—nothing too over-the-top, but that’s what makes them so easy to re-create or draw inspiration from. Take her recent look, for example.

Last week, while leaving an appointment in Beverly Hills, Aniston stepped out in what could only be described as the perfect summer outfit. She wore a black ribbed tank top, olive-green cropped trousers, and black flip-flops. Thanks to the trousers, the look struck the perfect balance between mature, elegant, and fresh. The olive-green colour gave them a sophisticated yet modern vibe, while the cropped cut added just the right amount of cool, laid-back energy. Furthermore, the trousers were a refreshing departure from the blue jeans we typically see on Aniston and other stylish A-listers. Plus, they're timeless and ageless, something I, a 20-year-old, would wear.

On Jennifer Aniston: AGCF Mayfair Bag

Inspired to add a pair to your rotation for summer 2025? Keep scrolling to shop the best olive-green trousers on the market.

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I love a '90s revival as much as the next person. Baggy jeans? I’m on board. Tiny sunglasses? Still into them. But my favourite comeback of all is one that’s been noticeably absent from the trend cycle—until now. After a few years out of the zeitgeist, the platform flip-flop trend is finally re-emerging and 2025 is shaping up to be the summer it makes its rightful return.

Unlike the minimal flat flip-flops we’ve seen dominate in recent years, this throwback style brings something new (and nostalgic) to the table: a bit of height. Though they fell out of favour for a spell as the trend cycle shifted, looks became more glamorous and the sandals were deemed "ugly" in comparison, now fashion people have seen potential in them once more.

Retaining all the comfort and ease of the classic beach sandal, the platform version adds a subtle lift that gives the shoes a sleeker energy. Beyond the comfort and added height, however, there's something inherently laid-back and cool about them. They evoke that carefree ‘90s energy we’re all still a little obsessed with—think Carrie Bradshaw in capris or Jennifer Aniston in cropped trousers. And fittingly, that’s exactly how we’re seeing them styled again in 2025. Fashion is, after all, cyclical, and these sandals are just the latest proof that some trends are well worth repeating.

Jennifer Aniston wears a pair of black platform flip-flops with cropped red trousers and a black tank top in 1999.

I’m clearly not the only one who's noticed their comeback. From high street heroes like Zara to high-fashion favourites like Coperni and The Row, brands across the board are serving up platform flip flops this summer. Whether reimagined in sculptural shapes, elevated materials or just sticking to the classic rubber sole, there are plenty of options to suit your preference.

Scroll on to shop our edit of the best platform flip-flops to wear this summer.

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When it comes to adjusting my wardrobe for a new season, I always catch myself thinking that I require a complete overhaul in order to make my existing pieces look fresh and relevant. It’s daft to assume that the answer to transforming my outfits throughout the months is to simply replace them when, really, all it requires is a simple but effective styling hack. Well, that is at least the case when it comes to summer jeans.

Forget about rushing to the high street to invest in the latest cut or wash. (But if you are in the market for a new pair, the trendiest jeans styles for 2025 are baggier and low-rise styles rendered in light indigo and white hues, in case you’re already on the hunt.) Indeed, if you need to rejuvenate a pair of Levi 501s or Khaite Danielles, you really only need to inject an additional element into your ensemble. Alexa Chung already proved the power of tying a scarf around your waist like a pseudo belt. But, if you’ve been paying attention to the latest style offerings from celebrities across London, Los Angeles and Cannes, you’ll know the latest trick is to actually overly cuff your jeans.

I know what you’re thinking—really, you’re suggesting cuff jeans as the solution to my outfit woes? And I completely understand your hesitation. The technique isn’t a recent development by any means. In fact, many an iconic ‘90s fashion paparazzi shot taken of the likes of Jennifer Aniston proves that celebrities have relied on this practice for decades.

But there’s something to say about how turning the hem up can improve a pair of trousers. This mode first piqued my interest when I saw Lila Moss wearing upturned jeans while out and about in New York City. At first, I wrote it off as a Gen Z fad, similar to how they roll down the band of their jeans. Then, I spotted Kendall Jenner out in West Hollywood utilising the same polished strategy.

Now, Emily Ratajkowski has stepped out during the Cannes Film Festival wearing her jeans the same way, making a hat trick of model off-duty moments using cuffed jeans and cementing this folding method as a certified trend to watch.

These outings may have just saved me from splurging on new denim, but it’s also a great reminder that if you feel like you need to breathe new life into trusty staples, you really only need to explore ways of bringing contrast or dimension into your look.

Don’t be surprised when you catch me wandering around town in a simple white t-shirt, cuffed baggy jeans and sweet ballet flats this season. If these looks have inspired you to give it a try, too, I’ve rounded up the essentials to replicate the cuffed jean trend at home. Discover them all, ahead.

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It’s a truth widely acknowledged that not all jeans and shoe combinations are created equal.

Jeans and heels can look amazing—if you find the right pairing. Trainers are a little more forgiving, but even they don’t work with every denim cut. Then there are shoes that I perceive to be tailor-made for jeans, and top of my list is Birkenstock’s iconic Boston clog.

Putting my theory to the test, Jennifer Aniston recently stepped out in the exact jeans-and-shoe pairing I genuinely think everyone could benefit from. Wearing a suede pair of Birkenstock Bostons, she styled the cult-favourite mules with slim-fitting, mid-wash jeans—neatly cuffed at the hem—a crisp white tee and a classic cross-body leather bag—creating an early-summer outfit that I can't find fault with.

A perennial two-piece look that fashion people return to once the sun starts to show, I’ve seen this combo on repeat during my London commute, but it’s also an L.A. staple, and I've seen this outfit on the streets of Amsterdam, too. No matter the city, the appeal is the same: easy, timeless style.

With your jeans and shoes sorted, building the rest of your outfit becomes a breeze. Take the style set's favourite route and keep it clean with a white tee, or lean into the trend and double up on the denim for a simple but striking look.

Shop our edit of the best jeans and Birkenstock Boston clogs now.

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As a fashion writer, I’ve built up a reliable roster of style muses who keep my inspiration levels high, but if I had to pick a forever favourite, it would be '90s-era Jennifer Aniston. Her approach to fashion during that decade was the blueprint for easy chicness: clean lines and unfussy staples that still feel incredibly modern today.

With summer pretty much in full swing, I’ve found myself revisiting her warm-weather looks in particular, specifically, the sandals she reached for time and again. As I build out my own seasonal wardrobe, I was delighted to discover that many of Aniston’s go-to ‘90s sandals are making a triumphant return for summer 2025.

If you’re looking to refresh your footwear game with pieces that are as timeless as they are trending, these are the '90s sandal trends worth copying from Jennifer Aniston this season.

3 SANDALS TRENDS JENNIFER ANISTON WORE IN THE '90S THAT STILL FEEL RELEVANT

1. FLIP FLOPS

Style Notes: Bringing an effortlessly cool edge to off-duty dressing, flip flops remain just as relevant now as they were across the '90s. Endlessly versatile: a classic black pair works as well with floaty dresses as it does straight-leg denim, and lends a relaxed polish to cut-off shorts and an oversized knit—just ask Aniston.

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2. FLATFORM SANDALS

Style Notes: As a fashion writer who regularly racks up a serious step count, my worlds often collide when I’m searching for sandals that feel elevated, both stylistically and literally, without inviting the inevitable blisters that come with them. Thankfully, the flatform trend is making a major comeback this season. Ushered in by the wider shift towards wedges, this ultra-comfortable silhouette offers a welcome boost of height without compromising on comfort.

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3. CHUNKY STRAP SANDALS

Style Notes: I’ll always have a soft spot for dainty strappy sandals, but this season it’s the bolder, thicker-strapped styles that are truly turning my head. Offering structure and support, these timeless sandals ground breezy summer outfits. This summer, I’ll be taking cues from Aniston and pairing mine with the floaty, romantic dresses already hanging in my wardrobe.

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As a fashion writer born in the '90s, my admiration for Jennifer Aniston feels almost inevitable.

She was the poster girl for effortless minimalism back then, and decades later, her style remains just as aspirational. From her era-defining Friends wardrobe to her polished off-duty looks, Aniston has always had an uncanny ability to make simple pieces feel iconic.

Having followed her style evolution for years, I can confidently say that whilst trends come and go, Aniston’s wardrobe is built on an unshakable foundation of timeless essentials. She flirts with fashion’s shifting tides but never strays too far from her signature aesthetic—refined, elegant and always effortlessly cool. And if there’s one thing I’ve learned from studying her looks? When Jennifer Aniston commits to a piece, it’s because it deserves a place in your wardrobe. Case in point: bootcut jeans.

No matter how many denim trends have cycled through—skinny, straight-leg, wide-leg, barrel—Aniston has remained unwavering in her love for this particular silhouette. And honestly? She’s onto something. As relevant now in 2025 as they were in 1995, bootcut jeans hug the hips and thighs before subtly flaring out past the knee, creating a beautifully balanced shape that elongates the legs and adds effortless movement to an outfit.

Though this denim hero has floated in and out of fashion over the years, the style set has officially declared a bootcut renaissance for this season. A shift toward boho-inspired dressing has propelled them back onto the runway, and culturally, they’re having a moment. Case in point: Kendrick Lamar’s Super Bowl halftime performance. With 133.5 million viewers watching, he casually reignited interest in the once-forgotten trend by styling a pair of Celine bootcut jeans—cue the internet frenzy. Fashion technology platform LTK has since reported a 350% increase in searches for bootcut jeans this week alone. It looks like Aniston’s long-standing love affair with bootcuts is finally getting the recognition it deserves.

Another group that has remained devoted to the retro denim trend? French women, of course. Effortlessly chic as always, they’ve been styling bootcut jeans for decades, pairing them with everything from slouchy tees and cosy knits to romantic blouses and sleek blazers.

With a mainstream revival now firmly underway, it’s the perfect time to embrace the silhouette that’s equal parts classic and cool. Read on for our edit of the best bootcut jeans to buy now.

SHOP BOOTCUT JEANS:

Fact: Rachel Green was the resident fashion girl of Friends throughout the series’ 10 season run. Sure, Monica had great taste in boots (despite not being able to walk in them), and we respect Phoebe’s charmingly eccentric ensembles, but Rachel had a penchant for wearing the most au courant trends of the times (the late ’90s and early ’00s). She also worked in the fashion industry for Bloomingdale’s and Ralph Lauren and is still our inspiration for styling overalls to this day.

It’s no surprise then that Rachel Green outfits are as relevant as ever. Ahead, we’ve outlined ensembles that show how Rachel became a style icon in the first place, and why she’s still deserving of the title. Keep scrolling for some of the hits from Friends’ own fashion girl, and then shop her key pieces.

Rachel Green Outfits We'd Happily Wear in 2025

!. Slip Dress

Style Notes: Slip dresses were essential for apartment parties as well as retail therapy.

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2. Black + Brown

Style Notes: Unafraid of a fashion faux pas, Rachel mixed black and brown into outfits without a care.

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3. High Neck Top + Check Shirt

Style Notes: Rachel Green in her namesake colour.

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4. LBD

Style Notes: Rachel didn't just do the LBD—she opted for an elegant qipao-inspired design.

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5. Cardigan + Plaid Trousers

Style Notes: Fortunately, we already have plaid trousers and a simple cardigan in our closets.

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6. Colour-Blocked Turtleneck + Mini Skirt

Style Notes: Colour-blocked turtlenecks are proof that Rachel has our winter wardrobe on lock.

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7. Denim Playsuit + Trainers

Style Notes: A playsuit and a blazer are unlikely bedfellows, but doesn’t it totally work?

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8. Gingham Dress

Style Notes: Gingham remains a spring/summer staple to this very day..

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9. White Tee + Jeans

Style Notes: No one rocks light-wash jeans and a white tee quite like Rachel.

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10. Skirt Co-Ord + Ankle Boots

Style Notes: A matching shirt and midi skirt is very 2025 (not to mention the black leather boots).

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11. White Top + Mini Skirt + Mary Jeans

Style Notes: The black miniskirt, t-bar Mary-Jane heels, and tucked-in top was a Rachel classic.

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12. Sleeveless Denim Vest

Style Notes: Even while working at Central Perk, she customised her uniform often, such as with this cool denim vest.

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13. Athleisure

Style Notes: Athleisure, ’90s style.

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14. Hawaiian-Inspired Shirt

Style Notes: She was even on board with the Hawaiian-shirt trend.

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This article was originally published at an earlier date and has been updated.

As someone who has watched the entirety of the Friends series more times than I would like to admit, it's safe to say that I have a soft spot for both '90s fashion and Jennifer Aniston. So, you can imagine my excitement when I came across an Aniston outfit that looked like it could have been plucked straight from the wardrobe of Rachel Green circa '96.

With a form-fitting silhouette and spaghetti-strap design, Aniston's '90s-inspired Reformation dress is in a dark burgundy hue and features a toned-down floral print throughout. Wearing the midi dress with a very Rachel Green-style shoe, Aniston selected strappy, pointed-toe heels in a matching colour to ground her look. Keeping her accessories simple and relaxed, the actor opted for a single pendant necklace in a ruby shade and wore two gold bangles stacked on her wrist.

With the dress composed of a breezy chiffon fabric, Aniston's outfit retained the effortlessly cool energy that her former character was renowned for.

To shop the high-street dress with Aniston's stamp of approval, read on to discover the Reformation Kourtney dress below, along with an edit of our other favourite Reformation dresses.

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We can all agree Jennifer Aniston has been serving Pinterest-worthy looks since the '90s. Now in her 50s, Aniston has cemented her signature style as unfussy, chic, and—thankfully for us—totally copyable. Although I'm in my 20s, I find myself looking to Aniston's paparazzi photos for fashion inspiration. Most recently, she's been seen in some especially easy-to-copy looks, inspiring this story. The stunning asymmetric Bottega Veneta midi dress she wore on The Tonight Show Starring Jimmy Fallon paired with strappy Saint Laurent heels is one ensemble I'd like to steal for myself. It's the epitome of how to perfect the little-black-dress look. In addition to press appearances, she has proven that her street style is also attention-worthy. The Murder Mystery 2 actress recently wore an effortless white tee and jeans that made for the perfect casual daytime outfit. Ahead, I re-created some of her standout looks with accessible brands we all know and love. 

See My Favourite Jennifer Aniston Looks:

1. An All-Black Ensemble

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2. An Easy One-Piece

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3. A Tonal Quiet-Luxury Look

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4. The Perfect LBD

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5. A Casual Jeans and Tee Combo

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Anyone that knows me knows that I absolutely love Friends. I must have seen each season about five times now, but there's something so comforting about the popular '90s show. Although I'm a big fan of each and every cast member, if I had to pick a favourite, it would definitely be Rachel. In fact, growing up, I was desperate to be just like her.

Whenever people ask me why, I give them a number of reasons. Not only did the character work in fashion, but she had the best wardrobe I'd ever seen, not to mention the best hair. It seems I'm not the only one obsessed with her choppy, layered locks, as Jennifer Aniston's haircut on the show was coined "the Rachel" a long while back, and it's currently having a major revival.

As you can see above, this cut usually sits at about shoulder length and contains lots of choppy layers that add volume to the hair. You can also incorporate face-framing layers or curtain bangs for the ultimate '90s look. Aniston famously added caramel and honey-coloured highlights to her hair back when she was filming the show, and I love how it lightens the layers and adds even more dimension.

Although the haircut was super popular when Friends first aired, I've been seeing lots of people re-create the look in recent years, and my TikTok feed is currently filled with people sporting the Rachel cut. In fact, the hashtag #rachelgreenhaircut has a whopping 12.9 million views. That and Rachel Green herself, Jennifer Aniston, just revived the layered style for her look at the 2024 Golden Globes, creating a viral moment in the process. With a longer finish and glossier colour, I'd go as far as to say her latest iteration of the style is even better than the OG. 

What I love about this style is that there are so many different ways to wear it, and everyone is giving it their own modern spin. From the butterfly haircut to the shaggy bob, there are lots of variations to try this autumn.

However, if you want to stick to Rachel's classic cut, keep on scrolling for some updated throwback inspo.

Rachel Haircut Inspiration

This haircut is giving me all of the '90s vibes, and it's safe to say that I'm obsessed.

For those who don't want to cut their hair to shoulder length or shorter, take a leaf out of Emily Ratajkowski's book and go for long, voluminous layers.

The Rachel cut works so well on curly hair, as you can see here. 

For seriously retro vibes, add some flicky layers into the hair.

A Rachel cut and a fringe? Sign me up.

So chic.

Jennifer Aniston has remained loyal to the look, revisiting it ad-hoc over the years. 

Zendaya is definitely channeling her inner Rachel as of late.

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Next Up: I'm Calling It—the "Hush Cut" Will Be Autumn's Coolest Hair Trend

There haven't been any new episodes of Friends in, well, ages, but the grip that Jennifer Aniston still holds over our collective style sensibilities remains strong. The actress was spotted in NYC promoting her latest project, Murder Mystery 2, wearing a head-to-toe cream-coloured outfit. Her gorgeous ankle-length beige overcoat made a statement while also showing off her barely-there nude Aquazzura stiletto sandals. 

Like Friends, the naked shoe trend continues to hold a place in our hearts. It's simultaneously timeless yet trendy and can be worn with just about any outfit. Plus, whether you choose to match a hue to your skin tone, or opt for the latest see-through vinyl versions, there's definitely a naked shoe out there that is bound to be a perfect fit. 

And, if you love the monochrome look but aren't super into beige, don't worry: neutral heels are invisible enough to wear with any colour and are guaranteed to make your legs look longer, even in jeans. So, channel your inner Aniston and prepare to step into this timeless trend.

Keep scrolling for 13 pairs of "naked" shoes that can be worn with anything (or nothing)—whatever suits your fancy. 

On Jennifer Aniston: Aquazzura So Nude Sandals (£525)

Shop Jennifer Aniston's Naked Shoes

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Next, Selena Gomez Wore a Fairytale-Worthy Wedding Dress While Filming in NYC

Just in time for autumn, Jennifer Aniston has exercised her influence to bring *the* denim trend for boot season back from the depths of fashion purgatory. While shooting The Morning Show in downtown Manhattan, the Friends alum was spotted wearing none other than a pair of bootcut jeans, a style that has gone largely unworn since the 2010s. The silhouette, which is fitted to the knee and flares out in order to encase a pair of boots, was replaced by skinny jeans at first and later by the vintage-inspired straight- and wide-leg jeans that reign today. But with a fan in Aniston, bootcut jeans could easily become the next big thing in the world of denim. 

With her dark-wash jeans, the actress wore a pair of point-toe black boots, a cropped blazer with gold buttons, and a fitted turtleneck, thus providing us with just as much outfit inspiration as her Friends character Rachel Green once did every Friday night on Channel 4. And with autumn arriving any day now, this autumnal ensemble couldn't have come at a better time. Below, shop Aniston's exact pair of bootcut jeans. Trust me—you won't be the only one. 

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Next Up: A Brow Pro Just Schooled Me on the Eyebrow Shape Mistakes for Every Age

This story originally appeared on Who What Wear US. 

Because A-list celebrities have access to the most expensive and exclusive skincare, makeup and fragrances, it's easy to assume that they use these expensive beauty products exclusively. And while they most likely have an impressive collection of eye-wateringly expensive fragrances, you might be surprised to hear that some of their favourite perfumes can be found in your local Boots. Yes, really. It turns out that celebrities such as Kate Moss and Gigi Hadid love an affordable fragrance just as much as we do.

After all, not everyone can drop £200 on a new fragrance, but affordable fragrances on the other hand allow you to build a fragrance wardrobe over time. So you can have an everyday signature scent for the daytime and then opt for something a little more exciting for the evening. And of course, you might want to wear a different scent for the summer months or bring out winter fragrances once the seasons change.

Zendaya is a fan of Lancôme's Idôle fragrance.

Sure, famous faces might have associations with a fragrance if they are the face of the brand's latest fragrance, however, there are plenty of celebrities who have spilt their favourite perfumes, and they're not paid to talk about them either. It seems it doesn't have to cost you a small fortune to smell like Zendaya or Hailey Bieber, after all. 

Ahead, we've found affordable fragrances that celebrities can't get enough of, and they are all available at Boots for under £90. Get prepared to add these celebrity favourites straight into your basket, and let the "What fragrance are you wearing?" compliments roll in. Because who wouldn't want to smell like a celebrity?

The Best Boots Fragrances That Are Loved By Celebrities 

1. Kate Moss: Clarins Eau Dynamisante

Kate Moss is a fan of Clarins Eau Dynamisante.

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2. Gigi Hadid: Giorgio Armani Acqua di Gioia

Gigi Hadid loves Giorgio Armani Acqua Di Gioia Eau De Parfum.

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3. Chrissy Teigan: Dior Hypnotic Poison

Chrissy Tiegan has previously shared that she is a fan of Dior Hypnotic Posion.

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4. Zendaya: Lancôme Idôle

Zendaya is the face of Lancôme's Idôle fragrance.

5. Ashley Graham: Chloé Eau de Parfum for Her

Model Ashley Graham reportedly loves Chloé Eau de Parfum for Her.

6. Hailey Bieber: Ariana Grande Perfume

Hailey Bieber has mentioned that she loves Ariana Grande's perfumes.

7. Dua Lipa: YSL Libre 

Dua Lipa is the fact of YSL's recently launched Libre fragrance.

8. Zoë Kravitz: YSL Black Opium Extreme

Zoë Kravitz is the face of YSL's iconic scent, Black Opium, but one of her favourites is the Extreme version.

Next: I Wore a Different Perfume Every Day for a Month—These 7 Earned Me Compliments

I wouldn't say that Jennifer Aniston and Jennifer Lopez have similar personal styles. The latter's tends to be much more bold and experimental. But here they are wearing identical outfit formulas in the same week in the same city. Who would have thought? They were both photographed in Los Angeles wearing black turtleneck sweaters, flared jeans and top-handle bags. Are you taking notes yet?

Flared jeans happen to be one of my favourite denim trends right now—one that I'm willing to swap out my beloved skinny jeans for. In my opinion, they're so much dressier than skinnies and help you look instantly polished. Scroll down to see how both well-dressed women style the same outfit combo and to shop similar pieces for yourself. 

On Jennifer Lopez: Hermès Birkin bag

Jen and Ben are still going strong. 

On Jennifer Aniston: Oliver Peoples Nisen Glasses (£279); Wolford turtleneck; Nili Lotan Oakland Jeans; Gucci Diana Bag (£2990)

Shop the Outfit Formula

1. Black Turtleneck 

2. Flared Jeans

3. Top-Handle Bag

Next Up: The 9 New-In Pieces I'm Adding to My Wish List This Week 

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

Ah, the '90s. An era defined by MTV, halter-neck tops, and more boy bands than we care to count. Some of our absolute favorite pop culture moments were born out of this decade, and when we think back on it, we can't help but relish in the wonderfully wild '90s hairstyles. And with the boom of the Y2K trend that we've seen over the last few months, it seems we're not the only ones who are feeling a little nostalgic.

From messy buns to a broad selection of fringes, and, of course, butterfly clips galore, there was something special about the hair trends from this time. The It girls of the era, such as Britney Spears, Janet Jackson, and Gwen Stefani, were serving up enough inspiration to carry us right into the following decade.

If you're as nostalgic as we are, then you'll love this roundup of the 20 most quintessentially '90s hairstyles we would low-key wear today. We might get some strange looks, but hey, we'll never shy away from an adventurous beauty look. Keep reading for our favourites.

20 of the Best '90s Hairstyles

1. Tiny Twists

The only thing that could make this style more '90s is a mini clip placed at the end of these tiny twists. This half-rolled hairstyle, also dubbed "picture-day hair" by the primary school set, ruled the decade.

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2. The Winona Pixie

The subtle layers and laid-back styling made this pixie cut an instant hit when Winona Ryder debuted it in the late '90s.

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3. Micro Braids

No one rocked micro braids quite like Brandy Norwood. This was her signature hairstyle on her hit TV show Moesha as well as in her real life.

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4. Bumped Bob

The soft curl added to this classic bob adds an interesting element to the hairstyle. Shown here on an angelic-looking Angelina Jolie, this spin on the bob would make us do a double take if we saw it walking down the street today.

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5. Feathered Fringes

There was a period of time when it seemed like every TV character was sporting these voluminous, feathered fringes. From D.J. Tanner to Kelly Bundy and, of course, Tiffani Thiessen's Saved by the Bell character, Kelly Kapowski, these bangs were the mark of a cool girl.

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6. Claw Bangs

On the other end of the fringe spectrum were these claw bangs, defined by face-framing, peekaboo pieces.

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7. Teeny Double Dutch Pigtails

This easy hairstyle screams '90s. Britney Spears fashioned her short haircut into two messy plaits fastened on the ends with elastics and just enough hair peeking out of the bottoms for a playful 'do.

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8. The Flip

From the pencil-thin eyebrows to the dark lipstick and the leopard-print collar, this photo of our queen Drew Barrymore is like a time capsule into the '90s. Her flipped hair (and those enamel hair clips) is another huge clue as to which decade we're looking at.

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9. Bedazzled Bandanas

Okay, so in all fairness, this photo was taken in the year 2000. But it's important to call out here because it exemplifies the influence that '90s hip-hop had on style and culture well into the decade that followed. J.Lo's bedazzled bandana accentuating her braided hairstyle is proof.

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10. Jumbo Box Braids

Janet Jackson's braids circa Poetic Justice were (and still are) a legendary look. The addition of this newsboy cap solidifies it as one of our favourite looks of hers.

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11. Butterfly Clips

Stefani wasn't afraid to push the envelope when it came to hair. But here, we see her adopting a trend that took hold of just about every '90s girl: the infamous butterfly clip. It was such a thing.

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12. Shortest Possible Platinum Pixie

Jada Pinkett Smith showed us plenty of short haircuts in the '90s, but this bleach-blonde, barely there cut was one of our faves.

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13. The Hilary Banks

Everything about The Fresh Prince of Bel-Air is a perfect representation of '90s life, but nothing compares to Hilary Banks's perfectly coiled coif, which she'd often top with a statement hat or oversize bow to tie her ensemble together.

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14. Messy Bun + Wispy Tendrils 

Don't be fooled by the name: The messy bun could be a super-chic look. Paltrow proved this point on a '90s red carpet, where she kept with the undone theme by letting some face-framing curls hang loose.

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15. The Rachel

Do we even need to explain? Didn't think so.

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16. The Sky-High Pony

Leave it to supermodel Tyra Banks to claim even more height with this sleek high pony. The flipped curl and swooshed bang add that much more '90s flair.

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17. Antennae

Nineties girls were all about an undone look, as evidenced by the trend of leaving just two straight strands of hair out in the front of an otherwise polished style.

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18. Two Braids

In an era marked by plenty of grungier looks, this almost childlike style really stood out. Note the clipped bangs as well.

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19. Chunky Highlights

Apparently subtlety just wasn't in style in the '90s. Kelly Rowland's highlights, coupled with her choppy cut, were clearly meant to stand out.

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20. Scrunchies

Scrunchie madness was such a defining trend of the '90s. They were perfect for securing any kind of ponytail or even just wearing around one's wrist like a bracelet. You know, just in case.

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This story was originally posted on Who What Wear US and has since been updated.

Call me a millennial cliché, but I’ve been a Friends fan for just about as long as I can remember. I’ve watched Ross and Rachel break up and make up and break up again, and I’ve hummed along to Phoebe’s "Smelly Cat” more times than anyone should. I don’t consider myself an expert on many things in life, but when it comes to Friends (and, of course, fashion), I can confidently say I know my stuff. So you can only imagine the sheer delight I experience when those two subjects collide. This week has provided a moment of exactly that.

Those who have seen the series umpteen times, like me, will remember "The One Where No One’s Ready.” And those who are fashion inclined will recall the stunning mint green dress Rachel wears in the episode. It is a quintessential example of ’90s minimalism done right, featuring a square neckline, thick shoulder straps and a side split that hits just above the knee.

Each time I watch the episode, I think about just how perfect this dress would be for a wedding or more formal occasion, and it seems like someone at the Whistles head office might have been thinking the same thing. The brand has recently launched a bridesmaid dress that is practically an exact replica of the iconic outfit. I’m not the only one who noticed. Author Dolly Alderton similarly spotted the resemblance…

Whistles’ iteration has the same fit as the dress Jennifer Aniston originally wore in 1996 and features a crossover detail at the back as well as an on-trend side split. While the label has marketed the maxi as a bridesmaid’s dress, it could definitely be worn for any other formal occasion you have coming up or as a wedding guest dress. I know where I’ll be getting my next outfit from. Keep scrolling to see the chic Rachel Green–inspired number and then shop more green dresses below.

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