’90s Supermodels Had Iconic Street Style — Here’s How To Recreate It

Plus, how to recreate them.

Linda Evangelista. Naomi Campbell. Christy Turlington. Cindy Crawford. This world-famous foursome redefined what it meant to be a model by originating “super” status decades ago. As emblems of pop culture, fashion and celebrity all wrapped into one, the ’90s supermodels transcended industries and even individual identities. And now, an in-depth Apple TV Plus docu-series is revisiting their rise to the top. They were, as the trailer teases, “larger than life.” This makes their street style all the more iconic.

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You see, it was through these documented outings that we got a glimpse of who the legends were as people. Via unexpected pairings and accessorizing accents, there’s a special kind of covert communication embedded in this sartorial self-expression. Here, FASHION breaks down the greatest street style hits of the ’90s supermodels — and how to recreate them.

Linda Evangelista

Thanks to her chameleon-catwalk abilities, Linda Evangelista holds a self-assured legacy in the supermodel sphere. “We don’t wake up for less than $10,000 a day,” she once famously uttered. The above picture — which shows her the Gianni Versace boutique in 1990 — surely explains why. The playful riff on power suiting is both glamorous and laid back, and it oozes know-your-worth confidence.

Uniqlo Pleated Wide Pants

Fitted at the waist with just enough slouch through the legs, these pleated trousers are the coziest way to emulate high-fashion street style. With a high-waisted cut, they can be easily styled with any cropped blouse or blazer. Plus, their elastic waistband is strategically hidden for a breathable wearer experience and a sleek aesthetic finish.

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Veronica Beard Nevis Cropped Jacket

Crafted with high-quality wool, this lightweight structured blazer is a transitional saving grace because of its styling versatility. Keeping with the Linda Evangelista ‘90s ensemble, it offers retro power shoulders and strong, sharp collars. The cropped length adds a cheeky playfulness for the ideal street style nonchalance.

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Ritoper Wide Headband

ICYMI, we’re in a headband renaissance. As luck would have it, Linda Evangelista’s athleisure hair accessory is the ultimate source of inspiration. Follow her lead with this 10-pack of non-slip black bands that are intended for all-day wear and every hair type, from textured curls to straightened strands. Not to mention, they’re crafted not to cause headaches. Because the first step in having a good time is getting your hair out of your face.

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Naomi Campbell

There’s a reason Naomi Campbell lives on basically everyone’s moodboard. From her captivating runway walk to her rumoured fashion feuds, the British model’s presence in the fashion sphere was never lacking personality. Pictured here on her way to an industry party in New York City, the ’90s legend opted for an all-white ensemble with individualized touches via chunky gold jewellery.

Allora Mini Dress

Similar to Campbell’s monochrome moment, the beauty of a crisp white mini dress is the possibilities it brings. Wear it with an unnecessary belt, layer on some fringe à la Naomi or keep it minimal for the Sofia Richie effect. Pro tip: Keep a crisp white button-up on hand to keep the chill off, and also, as an unexpected dupe in lieu of a handbag.

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Jenny Bird Walter Bracelet

As evidenced by Campbell, the chain-link bracelet is a chic outfit final touch. Both industrial and elegant, it elevates a simple ensemble by mixing masculine and feminine finishes. This gold polished piece by Jenny Bird encapsulates that magic. With an easy magnetic closure, the bold bangle sits comfortably on your wrist and can be worn on its own or layered with other statement pieces, like thick rings and pearlescent earrings.

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Christy Turlington

The magic of this look is that it is simultaneously so simple yet so good. Here, Christy Turlington makes the case for relaxed ‘90s cuts, gives a lesson in fall layering and offers inspiration for channelling your inner whimsigoth (the nostalgic TikTok-born aesthetic comprising cardigans, flowy maxi skirts and saturated tones). Seen on her way to a runway show at New York Fashion Week in 1993, her ludicrously capacious bag and glossy boots exude expert street style prowess.

Aritzia Babaton Monocle Shirt

Cut from buttery satin, this long-sleeved button-up blouse is a flowy favourite thanks to its laid-back fit and business-minded collar. Made from recycled materials and available in six colours, it’s a staple for the autumnal days in which you don’t want to think too hard when getting dressed. Take a page from Christy’s book and style it with billowy bottoms for loose and clean-cut silhouette.

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Sundry Long Relaxed Slit Skirt

A cozier take on Christy Turlington’s maxi, this ribbed cotton skirt epitomizes comfort-meets-chic dressing. Sundry specializes in refined weekend wear with a French fashion flare, and this piece is no exception. With its asymmetrical hem and soft side slit, the pull-on piece promises a polished final look.

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Sojos Classic Aviators

Sunglasses add a boost of intentionality to an otherwise low-maintenance outfit. In the above picture, aviators elevate Christy Turlington’s on-the-go ensemble. This vintage-inspired pair by Sojos has metal frames that bring the same retro charm with polarized lenses that help protect against harmful UV rays.

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Cindy Crawford

Putting a cool girl spin on traditional workwear is kind of Cindy Crawford’s calling card. Off the runway, the supermodel was known for her love of oversized leather jackets, worn both with Levi’s high-waisted jeans and mini skirts. In the above picture — taken in the Winter of 1990 — she paired the key piece with a turtleneck, a preppy tube skirt and a pair of sheer tights.

Frame Single-Breasted Leather Blazer

Toughened leather meets refined suiting with this oversized lambskin blazer. The single-breasted garment has a softly cinched waist for a statement silhouette that complements cold-weather outfits without completely concealing them. Wear it open with a skirt-and-shirt combo à la Cindy, or size-up and button it closed for a blazer-dress moment.

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Kotn Fitted Turtle Neck

Crafted from Egyptian cotton, Kotn’s fan-favourite turtleneck is soft and stretchy, thus hugging your curves without feeling restrictive. Wear it on its own on a crisp autumnal day or make like Cindy Crawford and pair it with a durable jacket for extra insulation. With five colours to choose from, it’s a fool-proof piece to add to your wardrobe rotation.

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Staud Annette Skirt

Reminiscent of Crawford’s striped skirt, this pinstripe print adds an air of playful prep to the archetypal mini skirt. With two front buttons and a hidden zip at the back, it puts a cheeky riff on classic corporate attire. Made with a lightweight stretchy fabric, it can be easily layered atop thin sheer hosiery or thicker tights on chillier days.

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