While other celebrities are experimenting with summer 2026 fashion trends such as jelly shoes, extra-baggy jeans, boho sandals, and capri pants, Jennifer Aniston is sticking to what she knows best: minimalism. For decades, she's kept her sartorial blinders on, ignoring fleeting trends—which is exactly why Aniston's '90s outfits look just as chic in 2026 as they did when Friends was still airing.

She wore her newest low-key look to a Los Angeles event promoting her Apple TV series, The Morning Show, to prospective Emmys voters. (Side note: On July 8, when Emmy nominations are revealed, we'll see if her efforts paid off.) She wore a Victoria Beckham Bela Midi Dress ($1350) with simple heeled sandals. If you don't have four figures to spend, may I direct your attention to Zara? The retailer has a bunch of dresses that feature the best detail of Aniston's dress: subtle draping. Scroll down to shop my favorites.

On Jennifer Aniston: Victoria Beckham Bela Midi Dress ($1350)

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If I had to describe Jennifer Aniston's '90s style in one word, it would be iconic. Whether she was off-duty on the streets of L.A. or on-screen as Rachel Green on Friends, she always stayed true to her style. She understood the power of elevated basics long before the word became buzzy, building her wardrobe around timeless, versatile pieces that still feel relevant today. Her staples included knee-length skirts, slip dresses, ribbed white tank tops, leggings, and relaxed jeans. For shoes, she loved simple open-toe heels but most notably white canvas sneakers. You could even make the case that Aniston helped popularize the style, turning a humble tennis shoe into a coveted item still to this day.

White canvas sneakers from brands like Keds, Superga, and Converse have long been classics, but since it's 2026, there's a new pair on the market that's competing for a spot, and in my opinion, it looks the most like Aniston's go-to pair while still looking modern and fresh. COS's Canvas Plimsoll Sneakers are them. The shoes feature three rows of waxed laces, tonal topstitching, and, most importantly, COS's elegant touch. The minimalist white tone allows you to style them similarly to how Aniston did or however your heart desires.

Keep scrolling to shop the COS sneakers as well as more white canvas styles from designers like Polo Ralph Lauren, The Row, and Nili Lotan

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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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At this point, shopping for jeans feels like trying to order from a restaurant serving twelve different types of cuisine. How can you possibly settle on one thing when the options are so varied? There are puddle styles that drag on the ground, rigid straight-leg jeans, polarizing skinnies that are making a comeback, and every possible barrel, flare, and horseshoe silhouette in between. Lately, though, I’ve found myself wanting something less extreme: relaxed but without exaggerated proportions. Enter Jennifer Aniston and her latest denim choice: baggy bootcut jeans that land squarely in that sweet spot.

While attending an event for designer Jenni Kayne's new book, Pacific Natural Everywhere, Aniston styled the denim shape in her signature low-key way with a simple black turtleneck sweater and classic pointed-toe ankle boots. Her jeans are just slouchy enough to feel modern, but the bootcut silhouette keeps them more streamlined than the extra-wide, extra-baggy styles dominating the market right now. They don’t cling to your legs, but they don’t swallow you whole either. Scroll down to see her outfit and shop similar pairs of jeans.

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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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Sometimes, looking back is the best way forward—at least when it comes to fashion. It tends to lean on nostalgia, and the main era it always seems to go back to is the '90s. There’s an essence of timelessness to that time period, especially when it comes to shoe trends. Certain shoe styles never go out of style, even if they are getting all the hype for a moment. This certainly rings true for all the shoe trends Jennifer Aniston wore during the '90s.

Fashion people, editors and influencers included, have been returning to these Jennifer Aniston–approved shoe trends. They somehow feel fresh and modern in 2026. Aniston was quite the fashion icon in the '90s, so it's no surprise that her appeal is lasting. If you love the classic touch '90s-inspired shoes add to an outfit, keep scrolling to shop the shoe trends that Jennifer Aniston wore in the '90s and the current fashion set in 2026 is obsessed with.

Pointed-Toe Pumps

This is as classic as a shoe trend gets. Pointed-toe pumps are my go-to for a night out, and the same can be said for all the cool It girls of 2026. You can wear your pair dressed up as Aniston did on the red carpet or give it a casual spin with jeans and a nice top.

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Strappy Sandals

Another trend Aniston often wore in the '90s was strappy sandals, which is perfect for the upcoming spring weather. I'll be wearing my pair with a flowy skirt and a simple T-shirt, but if you want to emulate Aniston, wear yours with a slinky little black dress.

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Mary Jane Heels

Mary Jane flats have already had a comeback, but Mary Jane heels feel a bit fresher. I love the way Aniston wore them in an episode of Friends with a simple white tee and miniskirt.

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Peep-Toe Heels

Peep-toe heels were popular last year, and I often saw them worn with jeans. This glamorous, effortless outfit Aniston wore inspires me to wear mine with more intention and dress them up.

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Snakeskin Boots

Snakeskin boots had a big moment in the fall, and the trend is still going strong. Aniston wore her snakeskin boots in a casual yet elevated way. Her suede-coat-and-jeans outfit is absolutely something I'd wear from head to toe.

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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's time, people! The 83rd annual Golden Globe Awards are finally here. It's the first award show of the season, and arguably, it's the most exciting. Why? It's simple. From a micro-perspective, it sets the standard for every award show that follows it, including the Grammys, the SAG Awards, and, finally, the Oscars in quick succession. From a macro-perspective, it sets the standard for the biggest beauty trends of the entire year.

Yep, we're about to see celebs like Ariana Grande, Tessa Thompson, Elle Fanning, Jennifer Lawrence, and more demonstrate the very trends that will dominate 2026. Without further ado, keep scrolling to see the best, most elegant beauty looks of the night. These beauty looks absolutely epitomize glamour and elegance.

Ariana Grande's Wicked character, Glinda, would approve of her pink cut crease.

Selena Gomez proves that "vampy" and "elegant" can truly go hand in hand. All it takes is a deep, ink-red lip color and a vintage-inspired bob.

Beauty products used: Chanel Le Vernis in Le Diable en Chanel ($33), Sublimage La Crème Texture Universelle Ultimate Cream ($485), and Sublimage L’Extrait Intensive Repair-Oil Concentrate ($765); Dr. Althea Aqua Marine Deep Serum ($13); Joico Hold Hero High Hold + Shine Boosting Finishing Spray ($23) and Dream Blowout Glass 72hr Frizz Fighter ($28)

Jennifer Lopez paired her signature glowing skin with shimmering purple eye shadow.

The cherry on top of Zoë Kravitz's effortless updo is a simple, chic flower pin.

Beauty products used: Cécred Nourishing Hair Oil ($44) and Hair & Scalp Balm ($44)

Jennifer Lawrence's French-girl bangs and thick black eyeliner deserve their own award.

Beauty products used: Dior Diorshow Liquid Liner in Satin Black and Satin Brown ($39), Backstage Rosy Glow Blush in Rosewood ($42), and Addict Lip Glow in Rosewood ($42)

Jenna Ortega brought her signature Wednesday aesthetic to the red carpet, and we're so here for it.

Beauty products used: Laduora Lumeo SkinLift 4D Current Red Light Therapy Kit ($215); Dior Diorshow Maximizer 4D Lash Primer ($35), Diorshow Overvolume Mascara ($38), and Diorshow 5 Couleurs High Color Eyeshadow Palette in Coral Flame ($70)

Ayo Edebiri's voluminous side part is right in line with the romantic, retro hairstyle trend.

Beauty products used: Olaplex Volumizing Blow Dry Mist ($30) and No.7 Bonding Oil ($30), Chanel Les Beiges Healthy Glow Foundation ($65), Ultra Le Teint Le Correcteur Concealer ($53), Les Beiges Healthy Glow Sun-Kissed Powder in Deep Mauve ($95), and Le Rouge Duo Ultra Tenue Liquid Lip Color in Intense Nude ($95)

Amanda Seyfried embodied Old Hollywood glamour with her architectural updo and eye-defining liner.

Beauty products used: Nuface Trinity+ with Lip & Eye Attachment ($495), Joico Hold Hero High Hold + Shine Boosting Finishing Spray ($23) and Defy Damage KBOND20 Power Masque ($39); GHD Chronos Curve Classic Curling Iron ($207); Parfums de Marly Valaya Eau de Parfum ($250); Vita Liberata Body Blur ($39)

For glowing skin, Kate Hudson is the official blueprint.

Beauty products used: Charlotte Tilbury Airbrush Flawless Foundation ($49), Unreal Lip + Cheek Glow Blush Stick in Peachy Glow ($42), and Beauty Light Wand in Pillow Talk Original ($42); Joico Hold Hero High Hold + Shine Boosting Finishing Spray ($23); Lashify Pre-Mapped Gossamer Lashes ($28), Whisper Light Bond ($26), and Waterproof Lash Sealer ($28)

Miley Cyrus's signature rock-chic aesthetic translates to the red carpet. All it takes is a smoky eye and highly contoured skin. Would you believe it if we said the whole look was created using drugstore products?

Beauty products used: Maybelline Lifter Plump & Glow Foundation ($16), Color Tattoo Longwear Multi-Use Eyeshadow Stix in I Am Determined ($12), Lash Sensational Sky High Mascara ($14), and Serum Lipstick in 008 Scuse Me ($8).

Emma Stone amplified her already sunny aura with glowing skin and glossy strands.

Beauty products used: Rōz Air Thickening Spray ($39), Milk Hair Serum ($52), and Evergreen Style Cream ($32)

Hailee Steinfeld debuted her baby bump for the first time on the Golden Globes red carpet. She was glowing with softly smoked-out eye shadow and Old Hollywood–inspired waves.

Beauty products used: GHD Duet Blowdry Hair Dryer Brush ($343) and Chronos Curve Classic Curling Iron ($207)

Tessa Thompson looked ethereal and mermaid-esque with long waves cascading down her back and glowy, glassy skin.

Beauty products used: SheaMoisture Silk Press Prep Cream ($14) and Bonding Amla Oil ($10); Sisley Paris Phyto-Teint Ultra Eclat N°2 Soft Beige ($120) and Phyto-Eye Palette 2 Bois de Rose ($125)

Meanwhile, Alison Brie debuted new Birkin bangs. We can't help but think this is how a French woman, specifically Jane Birkin, would do the Golden Globes red carpet. C'est très chic.

Beauty products used: Milkshake Blow Dry Primer ($28), Incredible Milk ($30), and Incredible Oil ($36)

Mia Goth's thick, winged liner and plump nude lips are understated yet impactful.

Beauty products used: L'Oréal Elvive Glycolic + Gloss High Shine Leave-In Serum ($8) and Elnett Satin Extra Strong Hold Hairspray ($14); Dior Forever Skin Perfect Foundation Stick ($57), Forever Skin Correct Full-Coverage Concealer ($42), and Diorshow Liquid Liner ($39)

Laufey's shiny, sleek ponytail is proof that vintage hairstyles are *it* for 2026.

No one does sculpted '90s-esque glamour like Lori Harvey.

Brittany Snow's lush lashes, rosy lips, and "champagne blonde" are a sophisticated formula.

Beauty products used: Kérastase Gloss Absolu Glaze Milk ($50) and Gloss Absolu Glaze Drops ($39)

We're putting Priyanka Chopra's hair on our 2026 beauty mood boards. Her feathered layers have so much body and dimension.

Beauty products used: Danucera D22 Tonic ($95), and Mega Serum ($165)

Emily Blunt looked elegant with rosy-brown makeup and a simple, slicked-back hairstyle. The real star of her look, though, was her glowing complexion. Her skin prep was completed by celebrity facialist Lord Gavin McLeod- Valentine using Augustinus Bader products.

Beauty products used: Augustinus Bader The Elixir ($550), The Face Oil ($250), and The Rich Cream ($315), Charlotte Tilbury Airbrush Flawless Foundation ($49), Beautiful Skin Sun-Kissed Glow Bronzer ($58), and Cheek to Chic Blush in Pillow Talk Intense ($42); Hair Rituel by Sisley The Cream 230 ($125) and Precious Hair Oil ($130)

Li Jun Li's stunning Golden Globes look is centered on three key elements: a bright pop of perfect red lipstick, fluttery lashes, and a wash of sheer pink blush to pull it all together.

Lisa proves glass skin and glossy lips won't go away in 2026.

Teyana Taylor is the ultimate cool girl with her shimmery eye shadow and vinyl-like lips.

Beauty products used: SheaMoisture Coconut & Hibiscus + Flaxseed Defining Styling Hair Gel ($9) and Coconut and Hibiscus Smoothing Oil ($10); Initio Parfums Privés Atomic Rose Hair Perfume ($100); Charlotte Tilbury Airbrush Flawless Foundation ($49) and Big Lip Plumpgasm in Nudegasm Diamonds ($35)

If you look closely, you'll see Amelia Gray's cool lavender eye shadow. We love a subtle pop of color on the red carpet.

Beauty products used: YSL Hyper Luminize Powder Highlighter in Lavender Lust ($55) on eyes and skin, and Loveshine Plumping Lip Oil Gloss in Thunder Stealer ($40)

Please excuse us while we find our mousse and texturizing spray to re-create Julia Roberts's voluminous waves.

Beauty products used: Lancôme Teint Idole Ultra Wear Care and Glow Foundation ($53), Teint Idôle Ultra Wear All Over Concealer ($32), Lash Idôle Flutter Extension Lengthening Mascara ($30), and L'Absolu Rouge Intimatte Buildable Soft Matte Lipstick in First Kiss ($35)

Pamela Anderson didn't wear a speck of makeup on the red carpet. Instead, she let her glowing skin shine—courtesy of her go-to Sonsie skincare products.

Beauty products used: Sonsie Super Serum ($64), Adapt Cream ($58), Multi Moisture Cream ($48), and Basic Balm ($22)

If it's not broken, don't fix it. Ana de Armas stuck to her signature look—soft makeup and voluminous hair.

Beauty products used: Estée Lauder Re-Nutriv Ultra Radiance Liquid Foundation ($140) and Futurist Blushmaker Dewy Cheek Tint Liquid Blush in Stolen Glance ($32); Kristin Ess Blow Dry Mist ($15), Dry Finish Heat Protectant Spray ($15), Dry Finish Working Texture Spray ($15), and Ultra Fine Workable Hairspray ($15)

Dakota Fanning's fresh-faced complexion was the star of her look.

Her sister, Elle Fanning, donned a similar petal-pink makeup look.

Beauty products used: L'Oréal True Match Super-Blendable Foundation ($10), Voluminous Panorama Mascara ($13), and Colour Riche Satin Lipstick in Peony Pink ($12)

Leighton Meester's fresh-faced complexion and wavy hair never miss.

Beauty products used: Bubble Cosmic Silk Hydrating Milky Toner ($16), Slam Dunk Moisturizer ($16), BondiBoost Everlast Airstyler System ($219); Beauty Pie Triple Beauty Luminizing Highlighter Wand ($25), Wondercolour Longwear Cream Eyeshadow Stick in Miracoli ($25), Supercheek Cream Blush in Fresh Faced ($25), and Velvety Matte Lip Crayon in Rummy Pink ($13)

Olandria Carthen's bold blush is so striking.

Makeup artist Mary Wiles let Sarah Snook's natural beauty shine by focusing on her glowing complexion rather than using bold makeup.

Beauty products used: G.M. Collin Biocellulose Face Mask ($115), Bota-Peptide Eye Contour ($92), Ceramide Comfort Serum ($125), Repair Lip Balm ($36), and Sensiderm Soothing Mist ($48)

Sometimes, it can take a while to figure out a new denim trend. We get so stuck in our jeans comfort zone, sticking only with straight-leg or barrel, not because we love them but because we know them—which brands make the best ones, which shoes look best with the shape, etc. So when an unfamiliar type—like cigarette jeans, for example—starts to garner popularity, it's easy to feel intimidated. Fortunately, Jennifer Aniston just wore a pair of the controversial denim trend and in doing so provided any newcomers with the key to styling them for everyday, casual wear.

It's all about styling cigarette jeans with pointed-toe boots. Simple, I know, but unlike ballet flats or loafers, pointed-toe boots help to elongate your legs, making you look like you shop in the tall department even if you're under 5'5". Cigarette jeans are already designed to give the illusion that you're taller, so combining them with pointed-toe boots only adds to the effect.

WHO: Jennifer Aniston

Aniston, specifically, wore a mid-wash pair with subtle distressing, styling them with a marled green sweater, an olive-green puffer coat, and a black hobo bag. She finished off the ensemble with pointed-toe black boots with a subtle Western look to them. The outfit was casual and cool yet put-together, making her look ready for any daytime occasion. She happened to be attending an event at Godmothers bookstore in Summerland, California, that was hosted by her boyfriend, Jim Curtis.

She's not the only person who's figured out how perfectly this denim-and-boot combination pairs together. From New York City to Rome, this sartorial duo is popping up everywhere, showing up on Who What Wear editor in residence Coco Schiffer, Emili Sindlev, and more. The trick is to find a pair of jeans that perfectly balances skinny and straight, with a slim fit that's just a touch long. That way, the denim sits on the foot of your boots in a cool, effortless way without puddling at all.

Scroll down to see how It girls are wearing cigarette jeans with pointed-toe boots, shop Aniston's outfit, and more.

Get the look: Contrast-collar barn jacket + Black sweater + Cigarette jeans + Pointed-toe black boots

Get the look: Colorful beanie + Barn jacket + Striped sweater + Cigarette jeans + Two-tone pointed-toe boots

Get the look: Black sweater + Dark-wash cigarette jeans + Black pointed-toe boots + Brown bag

Get Aniston's Look

Shop Cigarette Jeans

Shop Pointed-Toe Boots

Jennifer Aniston has had so many fashion eras she could have a stadium tour worthy of Taylor Swift's. Whether she was partaking in '90s layering during Friends, leaning fully into business chic several years later, or softening things up with a romantic floral Reformation dress just recently, Aniston has always looked polished, fresh, and impeccably dressed. It's not particularly surprising that any of us would aspire to own her entire closet.

In that spirit, I've gathered eight of Jennifer Aniston's best outfits from the '90s to now, each of which revolves around one specific wardrobe staple. For each category, I've found a handful of lovely clothing items and accessories that look very much like the original. Together, these eight items will create your very own Jennifer Aniston capsule wardrobe. It's as simple as that.

Oatmeal-Colored Coat

An oatmeal-colored coat is literally never a bad idea (except if it's 100° out, I guess). This color looks so effortlessly elegant and pretty much goes with every other hue, from brown and cream to royal blue and Barbie pink.

Brown Mock-Neck Sweater

I like a mock-neck because, as well as looking cute, it's less restrictive than a full-on turtleneck, which Aniston agrees with. Brown is lovely in the colder months too.

Black Wide-Leg Trousers

Wide-leg black pants are essential to a well-rounded wardrobe. Yes, they make ideal workwear, but they can also very much be a fashion item depending on how you style them. Aniston went for the all-black look here.

Floral Midi Dress

Reformation has the best floral midi dresses, as Aniston knows well, but I've found a great one from Zara too.

Leopard Bag

We all know leopard is a neutral, but it's also very handy for jazzing up an otherwise monotone outfit. It really pops against Aniston's navy coat here.

White Tank Top

I love a good white tank top. It's wild how something so basic can make your whole look as long as you pick the right neckline, straps, and fit.

Silver Sparkly Minidress

Though Aniston likes to stick to neutrals, she's definitely not above a little sparkle moment. The silver glitter on this frock is thoroughly party ready, and the long sleeves make it a tad more conservative. For variety, I've found both long-sleeved and sleeveless options for you to choose from.

Tan Trench Coat

The humble tan trench coat is hardly a revolutionary wardrobe item, yet it's one stylish women like Aniston come back to again and again. It's simple, it goes with everything, and it's perfect for in-between seasons.

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.

Shop the Outfit:

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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At Who What Wear UK, fashion is our speciality. Our editors have years of industry experience, from reporting on seasonal fashion trends seen at international fashion weeks to working with some of the most recognisable names in fashion. Every item we recommend is carefully selected based on current trends, quality and real-world wearability.

We regularly try on pieces ourselves—everything from best-selling jeans to designer shoes—and speak to external experts and fashion insiders, staying closely connected to what our readers are searching for. Our advice is grounded in expertise, and each and every buy we feature has to meet our exceptional taste standards—so you can feel confident in every recommendation.

Sneaker trends come and go. Slim, low-profile pairs and sporty retro styles are currently vying for the number one spot in the popularity charts, and chunky silhouettes, which were once all anyone wanted, are officially on the outs with fashion people. But there's one sneaker style that's immune to the trend cycle, making it a foolproof buy if you want to avoid the possibility that the comfortable shoes you wear multiple times a week will suddenly get moved to the "dated" pile one day. I'm, of course, talking about white sneakers, the timeless, versatile, and sleek-looking trainers that celebrities, athletes, models, and more have been wearing regularly for decades.

One such A-lister is Jennifer Aniston, who was spotted in New York City over the holiday weekend wearing a pair of white sneakers in a classic way. She styled the anti-trend sneakers with wide-leg jeans, a black tailored coat, and a leather flap bag from The Row. (Specifically, she was carrying the Nuance Hobo Bag, $2990.)

On Jennifer Aniston: The Row Nuance Hobo Bag ($2990)

Though I can't confirm which sneakers Aniston wore, photos of the actress show her in an all-white pair with a subtle platform. The lifted style allowed her to wear looser jeans without risking them dragging on the streets of Manhattan. Similar styles include Converse's Chuck Taylor All Star Move Canvas Platforms ($70) and Common Projects' Tournament Super Classic Sneakers ($470), a sneaker style she's been spotted in previously. Both are great choices if you, like Aniston, want your sneakers to provide an extra inch of height. If that's not a concern, you're still in luck. There's genuinely an endless supply of white sneakers for you to choose from, all of which have successfully beaten the trend cycle, ensuring that they'll never be considered "out."

Find your perfect pair of white sneakers below.

Get the Look

Shop White Sneakers

If you follow Jennifer Aniston's street style, you likely know that she has a penchant for denim. Whether she's arriving on set, heading to an appointment, or going out to dinner, she's most often wearing jeans. This fall, her favorite styles have included khaki cropped jeans, medium-blue straight-leg jeans, and slim-fitting cuffed jeans—a silhouette she wore this weekend paired with white sneakers.

While heading to dinner in L.A. with her boyfriend Jim Curtis, Aniston was spotted wearing a black sweater, a long black wool coat, low-waisted cuffed straight-leg jeans, and white sneakers. Staying true to her casual, low-key look, she skipped accessories and carried only an umbrella to keep dry in the rain.

A jeans-and-sneaker outfit isn't groundbreaking, but it is worth noting Aniston's pairing. For starters, cuffed jeans, especially a slim-fitting pair, are considered dated, as they were very popular during the '90s, often worn by Aniston. However, the way she styled them with crisp white sneakers, rather than the platform sandals and boots they were frequently paired with, made the jeans feel current and very 2025.

If you're inspired to replicate Aniston's casual yet elevated dinner outfit, keep scrolling. We've rounded up the chicest cuffed jeans and white sneakers for women.

Shop Cuffed Jeans and White Sneakers

In the late ’90s, no one mastered effortless style quite like Jennifer Aniston. One of her airport outfits from 1999, in particular, is still inspiring the chicest flyers in 2025. The look was disarmingly simple—a crisp white tee, a long gray cardigan, classic chino pants, and black clogs—but that’s exactly what made it timeless. I’ve always believed the best travel outfits strike the balance between cozy and pulled together, and Aniston’s formula still nails it decades later. Maybe it’s nostalgia or perhaps it’s the fact that most of us want to look presentable when we’re speed-walking to our gate, but this outfit continues to resonate. Every time I see a traveler wearing some version of it at airports in Los Angeles, Copenhagen, Paris, and New York, I can’t help but think Jen was ahead of her time.

That’s the energy I wanted to capture with this story: unfussy pieces that feel as current today as they did when Friends was still on the air. The renewed popularity of clogs certainly helps. And a long cardigan? It’s essentially a wearable blanket that also makes you look like you have your life together. When you combine those elements with chinos and a white tee, you get a travel uniform that works in any decade. Below, I’ve rounded up updated versions of each piece so you can channel Aniston’s iconic airport aesthetic.

Re-Create Jennifer Aniston's Best '90s Airport Outfit

If you’re a denim devotee, then you know exactly which brand we’re talking about. Levi's has dominated celebrity street style for decades. Its A-List fan base includes stars like Jennifer Aniston, Cindy Crawford, Hailey Bieber, and Kendall Jenner.

Lately, denim trends have favored ’90s styles (think baggy and slim-wide fits), confirming Levi 501s as the cult favorite once again. The Cinch Barrel, 94 Baggy, and Ribcage Straight Full Length Jeans styles also achieve that effortlessly cool, celeb off-duty look that fashion people love.

Luckily, for us, we can shop Hollywood’s favorite Levi’s at a massive discount this week during Amazon’s October Prime Day. Today is the last day Prime members can shop the best denim during Amazon Prime Big Deal Days 2025.

Hailey Bieber–Approved Levi's

Hailey Bieber goes ’90s with her vintage light-wash Levi 501s, striped polo sweater (a top sweater trend of fall 2025), and oversize leather bomber. The relaxed denim and preppy polo perfectly capture Bieber’s effortlessly cool style. Scroll on for the best on-sale Levi’s from Amazon Prime Big Deal Days 2025 to channel your inner Bieber.

What Do You Need to Know About Amazon Prime Big Deal Days 2025?

Prime members can start shopping for deals today. The two-day savings event ends today, October 8. Don’t have a Prime account? You can sign up for a 30-day trial before the sales begin.

While our editors are shopping the best beauty, home, and fashion steals of the season, I’m shopping the best denim deals. Here are the celebrity-loved Levi jeans starting at just $33.

The Best Levi's on Sale for Amazon Prime Big Deal Days 2025

Style Notes: Dakota Johnson pairs her Levi’s 501 ’90s with a red button-down shirt and leather loafers. She finished the look with circle-rimmed sunglasses—a great use of basics.

Style Notes: While out in L.A., Jenner paired her dark-rinse straight-leg Levi's with a cropped red tee, flip-flops, and an oversize tote. Shop a similar pair on Amazon.

Style Notes: Actress and model Kaia Gerber wears her high-waisted jeans with a black square-neck top, an open green button-down, pointed-toe heels, and orange sunglasses.

Shop More Jeans on Sale During Amazon Prime Big Deal Days Day 2025

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

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.

Shop Belts and Jeans:

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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If anyone has mastered the art of putting together a chic, '90s-inspired outfit, it's Jennifer Aniston, one of the many well-dressed women who inspired the easily-recognizable aesthetic back in her Friends days. While the '90s are long over, Aniston hasn't forgotten how to make simple pieces look elegant and elevated in that '90s way. She proved so on Tuesday night when she attended an after-party for the premiere of The Morning Show's new season at the Metropolitan Club in Manhattan, wearing an ensemble straight out of the era. Actually, all throughout the press tour for the show, she has utilized a specific '90s outfit combination for her looks, and yes, it's just as effective now as it was back then. Her styling trick? Pairing black dresses with barely-there strappy sandals.

What makes the duo so effective is how simple and timeless it is. Any black dress style will do, whether it's a strapless gown like the Rick Owens one she wore to the show's actual premiere or the V-neck, knee-length alt she changed into afterward. By going for super-clean heeled sandals (a custom Jimmy Choo pair with one toe strap and another slingback strap), she maintained an air of stress-free, effortless sophistication that perfectly describes street style from the decade.

On Jennifer Aniston: custom Jimmy Choo shoes

Aniston isn't the only one who knows how foolproof a black dress and strappy black sandals are. On the same night, Rosie Huntington-Whiteley was spotted outside Brasserie Zédel in London wearing a similarly '90s-esque look to the Elle Style Awards. For the occasion, the model chose a black Burberry minidress with a square neckline and V-shaped hem from the brand's F/W 25 collection. With it, she carried Burberry's Bridle Clutch, wore a selection of jewelry items from Tiffany & Co., and completed the night-out look perfectly with a pair of Aquazzura strappy black sandals.

On Rosie Huntington-Whiteley: Burberry dress and Bridle Clutch ($1995); Aquazzura shoes; Tiffany & Co. jewelry

Clearly, the combo is foolproof if a '90s look is what you're going for, whether you're heading to a red carpet event, a night out, or a dinner date. Whatever black dress you choose, your outfit will fall into place when paired with black strappy sandals. Trust me—it works every time.

When it comes to her style, Jennifer Aniston is nothing if not consistent. Whether she's on the red carpet in New York City or out to lunch in Los Angeles, she tends to rely on simple, all-black outfits (with a few neutrals like tan and gray thrown in for good measure). That's why I was surprised to see her wearing one of the boldest color trends of the year: royal purple. She allowed her vivid dress to take center stage by pairing it with understated pieces, including a black jacket and minimalist strappy heels.

Aniston's purple dress is reminiscent of an amethyst and is incredibly chic and memorable. And yes, it's worthy of a royal, too! According to History.com, "The color purple’s ties to kings and queens date back to the ancient world, where it was prized for its bold hues and often reserved for the upper crust."

Scroll down to see how Aniston switched up her style playbook for a press appearance promoting the newest season of The Morning Show in New York City today.

Shop the Color Trend

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

Isn't it nice when you invest in a shoe trend for one season, only to find out you can enjoy it and wear it again in the next? It saves you money and space in your closet. Plus, it makes you feel like a true fashion person—aka someone who knows what trends lie ahead. This is the case with a summer shoe trend that will continue into the fall: flip-flops.

This flat-shoe trend dominated in the summer, being worn by celebrities and fashion people in NYC, Copenhagen, L.A., Paris, and London with everything from denim to minidresses and midi skirts. Now, as the weather cools down and fall approaches, this casual yet elegant shoe style remains just as popular. But instead of skin-baring dresses and skirts, flip-flops are now being paired with jeans—straight-leg, wide-leg, barrel-leg, or whatever style you prefer.

On Jennifer Aniston: Tkees Liners Flip-Flops ($65)

One style muse who recently donned the look was Jennifer Aniston. This weekend, while heading to dinner with her boyfriend, Jim Curtis, in NYC, Aniston was spotted wearing light-wash straight-leg jeans with black Tkees flip-flops. On the top? A white T-shirt and a short beige jacket. While her look was simple, it stayed timeless and sophisticated as it relied on elevated wardrobe staples. With that said, keep scrolling to shop Aniston's sandals and chic jeans to pair with them.

Shop Aniston's Flip-Flops

Shop Straight-Leg Jeans and Flip-Flops

Nineties fashion hits different in the fall—it's a master class in textured suede fabrics, funky animal prints, light-wash denim, and all-black turtlenecks. Think Julia Roberts at LAX in her oversize blazer and light-wash jeans or Courteney Cox at a Hollywood premiere in a simple white button-down and slim trousers. The ultimate goal of '90s fall fashion was to achieve a casual elegance.

Every day, I wake up, look at my closet, and wonder how I can achieve that effortlessly cool '90s celebrity fall fashion look. I'm talking Jennifer Aniston, Halle Berry, Iman, Cindy Crawford, Elle Macpherson… The list goes on. Minimalism and clean lines defined the decade, with not a logo in sight, just elevated basics styled to look rich. That's precisely why each one feels so timeless and easy to replicate because chances are you already own a similar piece.

I can't get these 10 '90s celebrity fall fashion looks out of my head, so I've decided to re-create them with modern finds from Nordstrom (my go-to for all my fall shopping). Scroll down to discover the timeless '90s inspiration and how to wear it this fall.

10 '90s Fall Outfits to Re-Create This Season

Jennifer Aniston

Style Notes: '90s icon Jennifer Aniston is spotted in a blue miniskirt, black turtleneck and a long black overcoat.

Halle Berry

Style Notes: Actress Halle Berry wears an animal-print coat with a pair of light-wash denim and a velvet turtleneck.

Elle Macpherson

Style Notes: Australian model Elle Macpherson was potted at LAX in 1997 in a belted brown jacket, a classic black turtleneck, and kick-flare trousers. She grounds the look with a timeless pair of loafers.

Courteney Cox

Style Notes: Friends star Courteney Cox casually ties her sweater around her waist at a Hollywood premiere.

Tyra Banks

Style Notes: Tyra Banks wears a Canadian tuxedo paired with black leather Western boots and a backward cap.

Gwyneth Paltrow

Style Notes: Gwyneth Paltrow poses in a pair of leather pants and a fitted black turtleneck.

Kate Moss

Style Notes: Posing in a Saks Fifth Avenue store, supermodel Kate Moss sports a '60s silhouette. Her white miniskirt contrasts with her elegant black crewneck long-sleeve and pointed-toe ballet flat.

Iman

Style Notes: Iman wears an all-white ensemble at a premiere in NYC. The turtleneck underneath the ivory blazer elongates the chic look.

Cindy Crawford

Style Notes: Model Cindy Crawford arrived at LAX in 1991 sporting a leather blazer, straight-leg jeans, and a fitted black turtleneck.

Julia Roberts

Style Notes: Julia Roberts spotted at LAX in a very '90s 'fit. The oversize blazer complements the relaxed fit of the jeans.

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.

Shop the Best Khaki Jeans:

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 fall 2025 is khaki denim, and brands like Agolde, Citizens of Humanity, and Still Here 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.

On Jennifer Aniston: Tkees Flip-Flop ($60)

The denim color 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 color. 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 for styling ideas and pairs to buy now.

How to style: white T-shirt + khaki jeans + black sweater

How to style: black tank top + low-rise khaki jeans + flip-flops

How to style: black blazer + white tank top + khaki jeans + top-handle bag

How to style: leather bomber jacket + cropped khaki jeans + ballet flats

How to style: black tank top + cropped khaki jeans + strappy sandals

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.

Shop Simple Slip Dresses and Flip-Flops:

Jennifer Aniston, who starred in one of the most successful TV sitcoms of all time and popularized an iconic haircut in the '90s, has a self-confessed weakness for Instagram beauty recommendations. (Celebrities really are just like us!) That's according to a recent interview in which she shared her current skincare staples—two face creams that she discovered via social media.

While Aniston admitted that she doesn't use the same skincare products all the time ("My facialist told me it's important to rotate products. It's like muscle confusion for your skin," she said in an interview), I'll try anything that has the potential to make my 30-year-old complexion look as smooth, plump, and glowing as hers does at 56. Keep scrolling to see her two current skincare staples.

1. OneSkin's OS-01 Face Topical Supplement Essential Moisturizer

2. U Beauty's Super Tinted Hydrator

Shop 5 More Jennifer Aniston–Approved Products

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 love to see other people wear the sheer pants trend but have been hesitant to try it myself. While they can be cool and elegant, sheer bottoms can also be just plain scary to wear in public. Well, Jennifer Lawrence was just spotted in New York City utilizing a sheer-pants styling trick that I wish I'd thought of earlier. With just a month left of summer, I’m going to wear the sheer bottoms trend unabashedly now thanks to J.Law.

Lawrence layered a dress over her sheer pants and a relaxed, loose T-shirt over her dress. Layering may sound counterintuitive in the heat, but the breeziness of each piece makes up for it. Sheer bottoms and the skirt-or-dress-over-pants trend both had major moments last year and now are back in new ways for heat-wave season. Lawrence is also a loyalist of The Row, so it’s no surprise that her one pop of color came courtesy of a green Bourse Bag that she used as a clutch. For her shoes, she sported strappy Prada sandals.