If you spend any time on Who What Wear UK, you’ll know our obsession with the ‘90s runs deep. Between the straight-leg jeans, throwback movies (Clueless, anyone?) and unforgettable shoes, the nostalgia is something we hold close to our hearts. But. if we’re being really honest, it's the street style (the It girls' outfits, if you will) that are the best thing about the decade.

Whether you were into preppy streetwear, thought of yourself as a minimalist, or were loyal to grunge, the decade's most formidable women were unrivalled when it came to outfit inspiration. From Carolyn Bessette-Kennedy delivering daily masterclasses in understated elegance across Manhattan, or Aaliyah single-handedly making tomboy-chic cool again, the era was stacked with icons. And 20-or-so years later, their influence hasn't changed one bit; in fact, it's still defining how we dress today.

With so many great looks to choose from, whittling down a list of the ultimate ‘90s outfits was no small feat. So naturally, I enlisted the help of the chicest team in the business—the Who What Wear UK editors, of course. Beyond spotting the next viral trend and sniffing out expensive-looking finds at affordable prices, these women have an unmatched eye for style with true longevity. But don’t expect a slate of playing-it-safe neutrals: this list celebrates the bold, nostalgic and delightfully expensive side of '90s dressing too.

So if you’re in need of some outfit ‘inspo, or just wanting to take a nosy look into the minds of your favourite Who What Wear UK editors, now's your chance. Scroll to see the 10 best ‘90s outfits of 2026 worth recreating now.

10 It Girl Outfits From the '90s Our Editors Can't Stop Thinking About:

1. Carolyn Bessette-Kennedy

Style Notes: "To me, Carolyn Bessette-Kennedy represents all that was good and chic about '90s style. She never tried too hard (at least, she never let it look like she did), and the pieces she wore, she did so repeatedly. While you could definitely categorise many of her staples under "basics", she also had an eye for items with flair, case in point: her faux fur stole and leather coat. Throw in the perfect pair of blue jeans and a tortoiseshell Alice band and you have one of the '90s most iconic outfits—one that would look just as relevant on the streets of New York today. How many outfits from that decade can you say that about?" —Maxine Eggenberger, editor

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2. Julia Roberts

Style Notes: "Though I could reel off a whole list of '90s icons who have shaped the way I still dress today, there's only one outfit that occupies my mind on a weekly basis. When Julia Roberts stepped out at the Golden Globes in an oversized Armani suit and not an obvious gown, she was ahead of her time in a way that we're only just coming to realise. Where would the Frankie Shop, Toteme or even The Row be without this boxy silhouette? And, as someone who still makes the Saint Laurent spring/summer 2025 collection their entire personality (and has not one, but three ties), I don't think that there's anything cooler than big blazer energy, especially on a confident woman." —Remy Farrell, fashion editor

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3. Kate Moss

Style Notes: "Kate Moss proves that the classics are classic for a reason and can create a perfectly timeless outfit. Her black top taps into the three-quarter sleeve trend we’ve been seeing everywhere and pairs with absolutely everything, whilst the pop of white in the skirt provides the perfect contrast. And don't get me started on the styling hack of a top and shoes in the same colour. It's some of the best sandwich dressing I've seen, and I mean, Kate is a master at it after all." —Kitty Bovaird, social media editor

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4. Halle Berry

Style Notes: "We simply can't talk about the '90s without paying homage to one of the decade's ultimate style icons: Halle Berry. You see, what I adore about her playbook is her ability to master classicism with a clever twist. From her softly structured jeans to a sleek, fitted high-neck top, her intuitive use of texture and tone injects a healthy dose of personality into everyday basics. And when finished with a leopard print coat? Well, it's nothing short of absolute perfection." —Florrie Alexander, shopping editor

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5. Princess Diana

Style Notes: When it comes to iconic 90s outfits, Princess Diana has to get a special mention, but rather than her formal wear, it’s her off-duty, athleisure looks that I love the most. Diana was one of the first to make a trip to the gym look so chic, and the fact that these looks are still being recreated today says it all. Only she could make an oversized sweatshirt, gym shorts, and a designer bag look so cool and so royal."—Natasha Wilson, Videographer

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6. Aaliyah

Style Notes: For me, the ultimate 90s It Girl is Aaliyah (RIP). She was that girl before the internet even knew what it was. Everyone wanted to be her (or date her—Google it) because she was so fly, but also a bit of an enigma. Her '90s style definitely skews more tomboy and Matrix than mine, but she wore sports jerseys out of context just like I do, and I think I’m obsessed because no one else could pull off her proportion play so effortlessly and authentically.

Think oversized streetwear and baggy jeans styled with tiny crop tops that exposed her killer abs and belly bar. But also lashings of leather, silver accents and, like the other big African American stars of that era, lots of Tommy Hilfiger. Beauty-wise, I’ve often recreated her signature lip combo by outlining nude lips with a dark liner but, her eyebrow arches were a bit too high for me. —Felicia Pennant, branded content editor

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7. Jennifer Aniston

Style Notes: If you know anything about my personal style, you’ll know the pared-back minimalism of the ‘90s comes rather near and dear to my heart. And that means that Jennifer Aniston is one of my personal style heroines. Between the delicate sheer top, fitted black trousers and stylish T-bar sandal, this look is my outfit of dreams. The head-to-toe midnight palette keeps it minimal, understated and well within my comfort zone, whilst the sheer top and drop necklace add a subtle grunge vibe that I’m utterly obsessed with—all in all, this look gets 10s all around.—Brittany Davy, junior writer

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8. Winona Ryder

Style Notes: Let's be real; true cool-girl or It girl style isn't about desperately chasing the latest celebrity hype to prove your fashion literacy—it's an attitude, a feeling that comes from within. Which is precisely why my ultimate ‘90s style icon has to be Winona Ryder. Whether she's rocking a graphic tee on the red carpet, slipping into a velvet evening gown, or making a case for a V-neck jumper and midi skirts pairing, her outfits never felt overly forced or contrived. Every look was born out of comfort and nonchalance rather than a desire to dress to impress anyone. —Imani-Nia Francis-Tsolaki, junior fashion editor

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9. Victoria Beckham

Style Notes: "The little Gucci dress, the little Gucci dress or the little Gucci dress?” For a ‘90s girl growing up in the UK, it doesn’t get more iconic than the Spice Girls. Victoria Beckham was my queen (and my dark-brown bob as a kid meant I always got to be her at playtime), and Spice World has remained one of my favourite movies of all time. Posh was a smart, sassy ice princess with a wonderfully British sense of humour, and she didn’t need garish prints, maximalist accessories or brash logos; she just needed a pair of strappy heels and her little Gucci dress. The actual dress in that scene was from Miss Selfridge (it was the ‘90s; no one had any money!), which makes the whole thing even more perfect."—Georgia Seago, copy editor

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10. Cher

Style Notes: "Cher had '90s cool down to a science. Transitioning from her signature gothic-chic to something inherently more futuristic and dance-pop, she always came dripping in Chrome Hearts and looking impeccably stylish. My heart will always beat for you, Cheryl Sarkisian."—Nicole Pereira, junior social media editor

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I find myself going back and forth on whether jeans really work with heels. Sometimes, there’s too fundamental a mismatch between the utilitarian nature of denim and the polish of a heel; other times, the two look like a match made in heaven. In my opinion, the difference comes down to the jeans. Seasonal shifts in styling preferences play a part, too—I can’t see many of us rushing to pair skinny jeans with heels this season. So, which jeans-and-heel combination feels right for autumn/winter 2026 and actually looks great? I’ve done the research, and according to the style set, the answer is puddle jeans and heels.

Cascading past the ankles and grazing the floor, puddle jeans create an elongated silhouette that works particularly well with the sharp point of a heel. And I’m not the only one newly sold on the combination. In fact, I was put onto the pairing after spotting it multiple times on the streets of New York.

Styling the look for a Chanel event in the city, Halle Berry wore her low-rise jeans pooled at the floor, concealing much of her chic Chanel heels underneath. Finished with a single-breasted jacket, the look had me fully reconsidering jeans with heels.

While Halle’s take felt sharp and considered, Riley Keough approached the combination in a more relaxed way, styling her low-rise, baggy jeans with a tonal denim jacket. Worn over a simple white tank, the heels added a touch of elegance to the otherwise laid-back look, creating the kind of comfortable, wearable silhouette I’d gladly borrow.

With celebrity sightings under its belt, I’m now convinced that puddle jeans are one of the chicest denim styles to wear with heels right now. If you’re feeling inspired, read on to shop the puddle jeans and heels I recommend below.

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Yes, you can absolutely still wear jeans with trainers. Whilst the arrival of autumn makes a case for swapping out trainers for sleek leather boots and loafers, I’m not quite prepared to retire this comfortable pairing just yet. The key, to making the pairing feel dresh, as Halle Berry demonstrated this week, is choosing the right denim.

Spotted in a pair of cropped barrel-leg jeans, Halle styled hers with classic white trainers threaded with black laces. Not overly casual, the pared-back trainers balanced the volume of the jeans, whilst their bright white finish injected a fresh contrast to the dark denim.

Barrel-leg jeans may have taken something of a back seat this season after dominating this time last year, but their time is far from over. Their curved, voluminous silhouette gives them a more directional feel than your standard straight-leg pair, whilst the cropped hem keeps the overall look feeling polished and intentional. Paired with the contrast of a fresh white trainer and denim feels considered and chic. No need to resort to a heel, and not necessary to step out in a strict pair of loafers; I find that this pairing is as polished as the rest.

Below, I’ve rounded up the barrel-leg jeans and white trainers I’d happily wear together this autumn.

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Between jelly sandals, Carolyn Bessette-Kennedy-inspired fashion and statement cord necklaces, it feels like the ‘90s are officially back. But let’s be honest, this iconic decade has never really left us. But it’s undeniably more evident in 2026. And if there’s one nineties category that made the biggest mark this year, it would certainly have to be beauty. More specifically, '90s makeup looks are making a huge comeback this year, with some of the biggest trends being those we saw dominate almost four decades ago.

Now, we know that makeup trends come and go, especially in the age of TikTok, Instagram and YouTube, but there’s just something about a ‘90s makeup look that feels timeless, fitting right into the current zeitgeist without a second thought. Of course, there are trends that, as a makeup minimalist, would have had me running in the opposite direction: body glitter, bright blue eyeshadow and face gems, to name a few. But luckily for me, the it-girl-approved ‘90s makeup trends making a comeback in 2026 remain chic, timeless and, most importantly, feel extremely wearable.

Below, I’ve rounded up the seven key ‘90s makeup aesthetics that are set to dominate 2026. From playful pops of colour that are perfect for the upcoming summer season to the dark lip-liner trend that’s taken TikTok by storm, keep scrolling to see the ‘90s makeup looks trends that are making a comeback in 2026, plus the best beauty buys available so that you can get the look at home.

1. Statement Red Lip

We can't talk about '90s makeup without talking about a bold red lip. Unlike in the current day and age, when it's often paired with equally eye-catching smoky eyeshadows and statement blushes, in the ‘90s it was all about keeping the rest of the face pared-back and minimal, so as to let the lips do the talking (pun intended).

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2. Colour Pop

Vivid eyes, cheeks and lips were certainly all the rage in the '90s, and I can see why. These playful colour pops take a makeup routine from basic to elevated, and although I’m not ready to go all out with the trend, this pretty pinky-purple look on Naomi Campbell is slowly convincing me to try it out.

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3. Frosted

With “cold-girl makeup,” one of TikTok's latest obsessions, it should come as no surprise that the frosty aesthetic is making a comeback this year. Available in the form of everything from lipsticks to eyeshadows to highlighters, this icy makeup trend perfectly balances feeling cool and classic.

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4. Ultra-Matte

As someone with extremely dry skin, I’ve always been skeptical about recreating the ultra-matte bases that dominated the mid-90s. However, there are now plenty of products that give that blurring effect without sucking out every bit of moisture from the skin. So, I’m ready to give this long-lasting, sophisticated look a try.

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5. Dark Lip Liner

I’m not trying to brag, but I’ve been rocking the dark lip liner trend since I was a young teen. Between ultra matte blacks, cool-toned browns and deep burgundy hues, this is a trend that I can guarantee will never date.

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6. Ultra-Thin Brows

If you have thin eyebrows as I do, then you’ll be pleased to know that the ultra-thin brow trend, championed by the likes of Victoria Beckham, is officially back for 2026.

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7. Smoky Eye

For those more formal occasions, there’s nothing quite like a smokey eye. Although this mesmerising eyeshadow look has technically never stopped trending, I, for one, will be taking a cue from the likes of ‘90s icons such as Cindy Crawford and recreating this more subtle look for summer evenings out.

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I must admit when I think of summer outfits, my mind usually goes straight to floaty dresses, linen trousers, and basically anything else that lets my skin breathe. But here in the UK, where sunshine can switch to showers in a split second, jeans remain an essential part of the summer capsule wardrobe. And while denim might not scream “heatwave attire,” there are many ways to make them work for even the hottest of days.

One of the places I like to look to for inspiration is celebrity street style. Unlike the flashy red-carpet gowns and haute couture we often see them in, most celebrities' off-duty outfits are comfortable, chic, and, most importantly, easy to style. Think relaxed t-shirts, pretty blouses and lightweight but sophisticated tailoring- all clever but straightforward styling tricks that will make summer jeans outfits feel elevated and cool (in every sense of the word). Below, I’ve rounded up seven chic but wearable jeans-based outfits that I’ve spotted on stylish celebs this summer season.

From light-wash baggy jeans paired with halter-neck tops to seventies-inspired flares styled with trending boho blouses, keep scrolling for some summer jeans outfit inspiration.

8 Celebrity Jeans Outfits to Copy for Summer 2025:

1. T-Shirt + Turn-Up Jeans + Leather Flats

Style Notes: The white t-shirt and wide-leg jeans combo is a classic you can't go wrong with. To make it just that little more elevated, take a cue from Kendall Jenner, and opt for a pair of turn-up hem jeans and a shoulder bag in luxe fabrication such as suede.

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2. Halter Top + Straight Jeans + Flip-Flops

Style Notes: If this celebs have taught me anything, it's that the jeans-and-a-nice-top combo will never fail. So many stylish celebs have been spotted wearing this chic combo, but I especially love how Laura Harrier has incorporated a more structured top and contrasted it against the looser-fit straight jeans and pared-back flip-flops.

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3. Double Denim + Tank Top + Animal-Print Shoes

Style Notes: When in doubt, double denim will always be my go-to and I love the simplicity of Lori Harvey's Canadian Tuxedo paired with a plain white tank. To make this combo feel more '2025', follow her lead with a pair of snake-print boots. There's just something about animal print that feels so elevated but still remains within minimalists', like myself, comfort zones.

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4. Blazer + Ripped Jeans + Sandals

Style Notes: A plain tee and ripped jeans can feel a little casual, so opt for a tailored linen blazer to dress the combo up. Add a pair of sleek leather slides like Halle Berry has for an outfit that you can wear for a chilly summer day in town.

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5. Relaxed T-Shirt + Grey Jeans + Strappy Sandals

Style Notes: You can always count on Sienna Miller to take a classic outfit and make it edgy. The timeless t-shirt and baggy jeans pairing is actually from 2008, but remains relevant to this day.

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6. Cropped Tee + Wide-Leg Jeans + Slides

Style Notes: When the weather gets too hot, a cropped silhouette will serve you well. Keep things comfy like Jennifer Lawrence and opt for a flowy pair of wide-leg jeans with some easy slip-on Birkenstock slides.

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7. Suede Blazer + Bodysuit + Light-Wash Jeans

Style Notes: On those cold summer days, a soft suede blazer, as Dakota Johnson has opted for, will offset the rigidity of the denim and leather in this look. Add a simple bodysuit and let the luxe fabrications do the talking, not to mention it's a comfy but stylish base layer in case it gets too hot for the blazer.

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8. Lightweight Jacket + Flare-Kick Jeans + Wedges

Style Notes: Jeans and a flowy blouse is a timeless summer formula that works every time. To play even more into the boho feel, go for a pair of flared jeans and some wedges, like Jennifer Lopez has, to keep hems off the floor.

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How do you keep a blazer from looking too formal or worse, a little stiff?

Halle Berry has the answer—and it’s nothing short of alluring. Stepping out in New York, the actor gave a classic navy blazer a fresh, spring 2025 spin by styling it with one of the season's most talked-about trends: an elegant lace skirt.

Berry didn’t just opt for any blazer—she chose a sharply tailored, double-breasted style with smart pinstripe detailing, tapping into the pinstripe trend that’s been permeating style crowds while providing her outfit with a structured base. Contrasting the formal energy of her sleek outer layer, Berry wove a delicate energy into her evening outfit by way of her chic lace skirt.

Keeping her styling sleek with black pointed-toe heels and minimal jewellery, Berry let the sultry outfit take centre stage. Both strong and powerful yet very romantic, this clever combination creates a captivating ensemble that looks incredibly polished, despite being surprisingly easy to put together. It's not just her either—fashion insiders are backing lace skirts and dresses with full force this season. Styling them with wool coats, knee-high boots and fuzzy jumpers as we wait out the winter months, this trend will also prove to be a key silhouette throughout the spring season.

Obsessed with Berry's striking ensemble, below, I've curated an edit of the best pinstripe blazers and lace skirts. Read on to discover my selects.

SHOP PINSTRIPE BLAZERS AND LACE SKIRTS:

It's official: The stacked bob is back—but not in the way that you might know it. Google the hair trend and you'll be met with images of the "dated" style, which has exaggerated long layers at the front that ascend into heavily layered shorter pieces towards the back of the head, and this does give off 2010 vibes. However, I'm here to inform you that the stacked bob has had a modern update for 2024. Scroll down for the proof.

So how exactly is this type of bob haircut different this time around? Firstly, we're seeing a far softer graduation in those long-to-short layers, and this style is cropping up in a whole range of hair lengths. Chloë Grace Moretz's shoulder-skimming bob above has longer face-framing pieces, whilst Sabrina Elba has elegantly tucked those longer layers behind her ears in the cropped hairstyle below. You might also see this cut described as the graduated bob or micro bob, as hairstylist Tom Smith coins it.

"Shrinking normal bob lengths up close to the nape of the neck, the 'micro bob' is a great option for those willing to push the limits of the bob," he says. He explains that the hair is cut right up to the lowest part of the hairline and often styled in a head-hugging, sleek way. "This bob is a very high-fashion yet extremely practical option for those with straight to wavy hair," he says.

"Often styled with the hair tucked behind one or both ears, this is the natural progression of the 'contour bob' we saw a lot of during the spring, which encourages the shadows of a lifted cheekbone," says Smith. "It’s likely the micro bob will keep shrinking over the season, so those who typically wear a bob will enjoy the practicality of less hair to worry about over the summer." Stylish and practical? Yes please.

Ready to embrace the stacked bob? Scroll ahead for more haircut inspiration.

Stacked Bob Haircut Ideas

A full visor fringe looks so chic paired with those short, stacked layers towards the back of the neck.

Locs look great in this graduated bob, which compliments the jawline.

Proof that the side parting is timeless, Ciara's stacked bob has plenty of volume and bounce.

Halle Berry's stacked bob beautifully lets those curls shine.

Those longer sections at the front can be swept back behind the ears for an elegant look (and to show off statement earrings).

This graduated bob on Emma Willis has been styled for a rounded, concave effect.

Sabrina Elba has also sported a variation of the stacked bob with a choppy fringe, and we're into it.

The stacked bob also works with a swooping side fringe and flicky layers.

The Best Products to Style The Stacked Bob Hair Trend:

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

What do Nicole Kidman and Halle Berry have in common? They both just wore a thigh-high slit on the Oscars red carpet. Coincidence? We think not.

Risqué thigh-high slits have been a trend this year on both the runway and the people. Fashion brands such as Alexander McQueen and ACNE Studios exemplified in their recent collections that they are backing this trend. Seeing it on a red carpet as elegant as that of the Oscars truly cemented it into our minds. If you're bored of switching between micro minis and denim maxis, try a leg slit for change.

While we're talking about trends, another one to note that's popping up everywhere is the 3D floral motif that we refer to as a rosette here at Who What Wear. After seeing Zendaya strut a red carpet in this trend at the SAG Awards, we were 100% sold, so seeing it on both Kidman and Berry is music to our ears. 

On Nicole Kidman: Armani Privé dress

On Halle Berry: Tamara Ralph dress

Up Next: Florence Pugh Just Wore Short Shorts With a Flowing Train at the Oscars

This post originally appeared on Who What Wear US. 

Even though it was 18 years ago, it's hard to forget Halle Berry's turn as Bond girl Jinx in 2002's Die Another Day (which happens to be the same year she won her Oscar for Monster's Ball). And one of the most unforgettable scenes was the one in the orange bikini. You know the one—Berry walked down the beach in a string bikini and holster and everyone lost their minds. If "breaking the internet" was a thing back then, she would've. 

So why are we bringing this up nearly two decades later? Well, Berry just graced our Instagram feeds with a very similar photo of her walking down the beach in a very similar belted orange bikini. And just like that, we want an orange bikini of our own. If that's the case for you too, keep scrolling to shop our favorite orange bikinis and to see how amazing Halle Berry today and 18 years ago in the style.

2002

2020

Shop Our Favorite Orange Bikinis

Next up, see our guide to the key trends for spring summer 2020.

The Vogue September issue is always one of the most anticipated issues of the year, and now the publication just added a little more excitement. According to Fashionista, you can now pre-order the September issue on Amazon ($6) if you are a Prime member. It will arrive in your home on August 14, five days prior to the newsstand release date of August 19. Not only that, but it will come in a custom, limited-edition Vogue box, and you can even have it gift-wrapped if you like. Now we just have to find out who's on the cover…

Scroll down to see past Vogue September issue covers!

Shop the Vogue September Issue on Amazon!

Who do you hope to see on the cover of Vogue's September issue? Tell us below!