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

(Image credit: Getty Images)

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

Shop the Look:

H&M Leather Coat

So '90s.

COS Clean Cut T-Shirt

A bestseller.

YSL Yves Flared Jeans

These jeans have been everywhere this year.

Massimo Dutti Leather Heel Ankle Boot

Carolyn-coded.

JENNIFER BEHR Lydia Tortoiseshell Acetate Headband

A timeless accessory.

2. Julia Roberts

(Image credit: Getty Images)

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

Shop the Look:

Massimo Dutti Pinstripe Cool Suit Blazer

Almost Julia's blazer, with a 2026 update.

With Nothing Underneath The Boyfriend:

A timeless design.

Massimo Dutti Pinstripe Cool Wool Blend Suit Trousers

I love how these low-waisted trousers would look styled with a funnel-neck jumper and ballet flats.

ASOS DESIGN Tie in Polka Dot

Any purple printed tie will do.

Sezane Markus Loafers

Not a want, but a need.

3. Kate Moss

(Image credit: Getty Images)

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

Shop Her Look:

Cou Cou Intimates The French Midi Sleeve Cotton Jersey

London-based brand Cou Cou Intimates are known for their '90s-inspired silhouettes.

Geel Aria Skort

You could also style this skirt with a loose shirt and ballet flats on a warmer day.

Ralph Lauren Londyn Leather Ballet Flat

The perfect pointed-toe flat.

Daisy Jewellery Engravable Pinky Signet Ring

The perfect finishing touch.

Aspinal of London Floating Diamond Solitaire Stud Earrings

Can you ever go wrong with a pair of diamond studs?

4. Halle Berry

(Image credit: Getty Images)

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

Shop the Look:

NOUR HAMMOUR Nina Tiger-Print Shearling Coat

For a 2026 update, why not try a leopard print coat with a sumptuous fur trim.

ZARA Extra-Soft 100% Wool High Neck Jumper

I'll be swapping Halle's velvet high-neck top for a matte black iteration instead.

AGOLDE 90's Mid-Rise Straight-Leg Jeans

A fashion person's favourite style.

M&S Leather Block Heel Square Toe Boots

M&S make some of the comfiest boots on the market.

Nere Stori Knit Overnight Duffle Bag

All we need now is a trip to a balmy destination.

5. Princess Diana

(Image credit: Getty Images)

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

Shop her Look:

Sporty & Rich Usa Knitted Sweater

Size up for a looser fit.

lululemon Align™ High-Rise Short 6"

A style you can take from the gym to the streets.

Reebok Club C 85 Vintage Trainers

Whilst her iconic Reebok trainers may still be discontinued, the Club C shape has a similar energy.

M&S Leather Bowler Bag

A timeless design.

Le Specs Outta Love

You can never go wrong with a pair of winter sunnies.

6. Aaliyah

(Image credit: Getty Images)

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

Shop the Look:

H&M Denim Shirt

Its not time to pack away your white denim just yet.

Guess Lucy

I love how a distressed brown vest adds depth to her denim shirt.

COS Chord Straight-Leg Jeans

I have it on god authority the COS's chord jeans are some of the very best.

Jimmy Fairly The Emmy

A classic.

Cartier D'amour Pendant, Brilliant-Cut Diamond

Diamonds are a girls best friend after all.

7. Jennifer Aniston

(Image credit: Getty Images)

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

Shop the Look:

SARA CRISTINA Nerea Embellished Crochet-Knit Cotton Top

A smart way to style your summer crochet.

Victorias Secret Black Unlined Balcony Lace Bra

Every day can feel like a fashion show with the Victoria's Secret Balcony Lace Bra.