10 Iconic ’90s Celebrity Outfits to Wear This Winter

’90s style still feels useful because its best outfits were built around a point of view, not a pile of new pieces. Carolyn Bessette-Kennedy made repeated basics look deliberate; Julia Roberts showed the ease of an oversized suit; Aaliyah made sporty proportions feel personal. For winter 2026, those ideas translate into practical combinations of coats, knitwear, denim and accessories, with room for both pared-back dressing and bolder choices.

The decade’s references range from minimalism and preppy polish to grunge and streetwear. The looks below, selected by Who What Wear UK editors, show why they keep resurfacing: each has a simple styling idea that can be adapted to what’s already in your wardrobe.

Polished basics, with one memorable detail

Carolyn Bessette-Kennedy: denim and a leather coat

For editor Maxine Eggenberger, Bessette-Kennedy’s appeal is the balance between an unfussy foundation and a piece with character. Blue jeans, a leather coat and a tortoiseshell headband make a composed combination without looking overworked. The repeat-wear approach is part of the point: familiar pieces gain impact through fit and one considered accessory.

For a winter version, start with H&M’s Leather Coat, a white COS Clean Cut T-Shirt and Saint Laurent Yves Flared Jeans. Massimo Dutti’s Leather Heel Ankle Boot keeps the line sleek, while the JENNIFER BEHR Lydia Tortoiseshell Acetate Headband supplies the finishing detail. A faux-fur stole can add texture, as can a leather coat with a strong shape.

Julia Roberts: borrow the suit

Julia Roberts’s oversized Armani suit at the Golden Globes remains a persuasive alternative to a gown. Fashion editor Remy Farrell sees its boxy proportions echoed in labels such as The Frankie Shop, Toteme and The Row. The look’s staying power comes from its confident mix of tailoring and ease.

Build a winter take with a Massimo Dutti Pinstripe Cool Suit Blazer, matching Pinstripe Cool Wool Blend Suit Trousers and a white With Nothing Underneath The Boyfriend shirt. A purple printed ASOS DESIGN tie makes the reference more playful; Sézane Markus Loafers ground it. For an alternative winter styling, wear the low-waisted trousers with a funnel-neck jumper and ballet flats.

Kate Moss: a sharp black-and-white contrast

Kate Moss makes a strong case for a black top, a white skirt and shoes that repeat the top’s colour. Social media editor Kitty Bovaird calls the effect “sandwich dressing”: matching the top and shoes frames the contrast in the middle. A three-quarter sleeve adds a current note without changing the formula.

Try the black Cou Cou Intimates The French Midi Sleeve Cotton Jersey with the white Geel Aria Skort and pointed Ralph Lauren Londyn Leather Ballet Flat. On a warmer day, the skort can shift to a looser shirt and ballet flats. A Daisy Jewellery Engravable Pinky Signet Ring and Aspinal of London Floating Diamond Solitaire Stud Earrings keep the accessories restrained.

Halle Berry: everyday pieces meet animal print

Shopping editor Florrie Alexander singles out Berry’s combination of softly structured jeans, a fitted high-neck top and varied textures. The leopard-print coat is the pivot: it gives familiar basics a clear focal point without demanding a complicated outfit.

For a cold-weather interpretation, layer a NOUR HAMMOUR Nina Tiger-Print Shearling Coat over a matte-black ZARA Extra-Soft 100% Wool High Neck Jumper and AGOLDE 90’s Mid-Rise Straight-Leg Jeans. M&S Leather Block Heel Square Toe Boots finish the look; the Nere Stori Knit Overnight Duffle Bag adds a practical soft-sided accessory.

Sporty ease and confident proportions

Princess Diana: athleisure beyond the gym

Videographer Natasha Wilson points to Diana’s off-duty formula: oversized sweatshirt, gym shorts and a designer bag. Its appeal lies in taking athletic clothes into everyday styling, with relaxed proportions doing the work. For winter, a sweatshirt can sit over shorts with opaque tights, or the pieces can be worn separately when temperatures call for layers.

Choose the Sporty & Rich USA Knitted Sweater in a looser fit, lululemon Align High-Rise Short 6" and Reebok Club C 85 Vintage Trainers. The Reebok Club C has similar energy to Diana’s discontinued trainers. A M&S Leather Bowler Bag and Le Specs Outta Love sunglasses bring the street styling into focus.

Aaliyah: streetwear with proportion play

Branded content editor Felicia Pennant remembers Aaliyah for oversized streetwear, baggy jeans and small tops, styled with leather, silver accents and plenty of Tommy Hilfiger. Sports jerseys worn outside their usual setting were part of the attitude. The styling still works because volume and close-fitting pieces give each other definition; choose the balance that feels comfortable to wear.

A white H&M Denim Shirt, brown Guess Lucy Waistcoat and white COS Chord Straight-Leg Jeans offer a layered take on the look. Add Jimmy Fairly The Emmy glasses and a Cartier D’amour Pendant, Brilliant-Cut Diamond. Pennant’s beauty reference is equally specific: nude lips outlined with a darker liner.

Minimalism, nonchalance and evening polish

Jennifer Aniston: midnight tones with a sheer layer

Junior writer Brittany Davy’s Aniston reference pairs a delicate sheer top with fitted black trousers and T-bar sandals. A near-monochrome palette keeps the silhouette quiet, while a slouched necklace introduces a subtle grunge edge. For winter, keep the dark foundation and use a layer underneath the sheer fabric for warmth and coverage.

Try the SARA CRISTINA Nerea Embellished Crochet-Knit Cotton Top over the Victoria’s Secret Black Unlined Balcony Lace Bra, with Massimo Dutti Skinny Flare Fit Pants and a Lovisa Gold Plated Y-Necklace. Steve Madden Mizuna Black Heeled Sandals carry the evening feel; the velvet trousers also work with a fringed top and heels.

Winona Ryder: clothes that look lived in

Junior fashion editor Imani-Nia Francis-Tsolaki describes Ryder’s style as instinctive rather than calculated. A graphic tee, velvet gown or V-neck jumper with a midi skirt could each feel like her, because comfort and nonchalance came first. That makes this one of the easiest references to adapt for cold weather.

Start with a Massimo Dutti Wool Blend Knit V-Neck Sweater and Gap Herringbone Knee-Length Skirt. ZARA Studded Heel Sandals sharpen the pairing, while the Saint Laurent Mombasa Medium adds texture. For everyday wear, a graphic tee can replace the knit when the weather allows.

Victoria Beckham: the little black dress

Copy editor Georgia Seago’s memory of Victoria Beckham is tied to the Spice Girls and the little Gucci dress in Spice World. The actual dress in that scene was from Miss Selfridge, a detail that gives the reference its own down-to-earth charm. The styling is still legible: a simple mini dress, strappy heels and very little embellishment.

A Norma Kamali Ruched Stretch-Jersey Mini Dress and Topshop Wren Peep Toe High Heel Sandal keep the silhouette streamlined. Add the Pandora Shimmering Black Cord Bracelet for a small glint of gold. In winter, layer with a coat and opaque tights while letting the dress remain the focus.

Cher: gothic detail meets futuristic shine

Cher’s ’90s style moved from gothic-chic toward a more futuristic, dance-pop mood, with Chrome Hearts among the reference points. Junior social media editor Nicole Pereira’s outfit picks translate that mix through leather, paisley, a crystal choker and a compact bag. It’s the boldest formula in this edit, and its pieces can be dialled up or down individually.

Layer a white ZARA Ribbed Sleeveless Top under the paisley DESTREE Amoako Devoré Blazer, then add AGOLDE Nate Leather-Blend Tapered Pants. A JENNIFER BEHR Sophia Crystal-Embellished Velvet Choker and Miu Miu Leather Mini-Bag finish the look. The useful winter takeaway across all ten references is simple: pick one signature element, then let the rest of the outfit support it.