The Iconic '90s Celeb Outfits Our Editors Would Wear This Winter

If you spend any time on Who What Wear UK, you’ll know our obsession with the ‘90s runs deep. Between our school days (for the millennials amongst us), the throwback movies (Clueless, anyone?) and, of course, the unforgettable fashion, we hold the nostalgia close to our hearts. But what it really comes down to is the decade's street style.

Whether you were into the preppy look, thought of yourself a minimalist or were loyal to grunge, the decade's most stylish women were unrivalled when it came to outfit inspiration. From Carolyn Bessette-Kennedy delivering daily masterclasses in understated elegance across Manhattan to Aaliyah single-handedly making "tomboy-chic" cool, 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 the ultimate ‘90s celebrity 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, cool and delightfully fun side of '90s dressing too.

Scroll to see our favourite '90s It-girl outfits and how to re-create them in winter 2026.

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 wore repeatedly. Whilst 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 headband, 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 constantly occupies my mind. When Julia Roberts stepped out at the Golden Globes in an oversized Armani suit—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 from the skirt provides the perfect contrast. It's one of the best examples of "sandwich dressing" (top and shoes in the same colour) 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 the 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 instead of her formalwear, it’s her off-duty athleisure looks I love the most. Diana was one of the first to make a trip to the gym look so chic, and the fact that this look is still being re-created 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, Aaliyah was the ultimate '90s It girl. She was that girl before the internet turned it into a thing. Everyone wanted to be her (or date her—Google it) because she was so fly, but also a bit of an enigma. Her style definitely skewed more tomboy and Matrix than mine, but she wore sports jerseys out of context just like I do, and 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 re-created her signature lip combo by outlining nude lips with a dark liner." —Felicia Pennant, branded content editor

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7. Jennifer Aniston

Style Notes: "The pared-back minimalism of the ‘90s is very close 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 sandals, 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 slouched necklace add a subtle grunge vibe that I’m utterly obsessed with—all in all, this look gets 10s all around from me." —Brittany Davy, junior writer

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8. Winona Ryder

Style Notes: "Let's be real: true It-girl style isn't about desperately chasing the latest celebrity hype to prove your fashion literacy—it's an attitude. This 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-skirt pairing, her outfits never felt overly forced or contrived. Every look was born out of comfort and nonchalance rather than a desire 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 didn't get more iconic than the Spice Girls. Victoria Beckham was my queen, 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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