5 ’90s Trouser Trends to Supercharge Your Wardrobe in 2026

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We’ve always loved the ’90s–but, in 2026, we really love the ’90s. Blame Ryan Murphy’s Love Story for introducing a new generation to Carolyn Bessette Kennedy, or simply an even more fervent nostalgia for an era of no smart phones and more affordable apartments. And, as ever, it’s affecting the way we dress. From the clean-lined silhouettes that defined peak ’90s minimalism, to a fresh affection for the era’s accessories–like headbands, silk scarves, and plain hoops – fashion’s most low-key yet copycatted decade is back at the forefront of the conversation.

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The Capri
The Park Allison Capri pants
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The Cigarette Jean
Levi's 501 90s jeans
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The Bootcut Trouser
Banana Republic ponte ankle pants
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The Cargo Pant
Leset Kyoto pants
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High Sport Kick cropped flared pants
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You’ve got a pair of strappy heels or block boots–but what else to wear on your bottom half? Below, five ’90s-inspired trouser trends we’ll be wearing in rotation this year.

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Capri Pants

Capri pants, which had a moment in the 1950s and ’60s, and then again in the late ’90s and early 2000s, are one of those weird garments that shouldn’t work but somehow just do–especially with a little low-rise heel and a spaghetti strap top. They were all over the spring/summer 2026 runways (see: Versace, Ralph Lauren and Isabel Marant), and are beloved by the likes of Kendall Jenner and Bella Hadid, too.

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The Park

Allison Capri pants

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Leset

Rio capri pants

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Cropped Trousers

Often, the secret to a flawless ’90s look isn’t in the item of clothing, per se, but the cut. Case in point: the beautifully tailored cropped trousers worn by the likes of CBK, Gwyneth Paltrow and Winona Ryder back in the day. Most often worn with a blocky boot or minimal loafers, cropped trousers are the business-casual option that can do it all.

Leset

Rio cropped flared pants

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High Sport

Kick cropped flared pants

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Cigarette Jeans

I may have written about cigarette jeans roughly one thousand times during my time at British Vogue, but I don’t intend to stop today. That’s because they’re the perfect jeans for 2026–pared-back, minimal and more polished than their baggier counterparts. If you want to fully lean into the decade, à la Cindy Crawford and Courteney Cox, then style them with ’90s boots and shades.

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Re/Done

90s straight leg jeans

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Levi's

501 90s jeans

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Bootcut Trousers

There’s something distinctly satisfying about the type of bootcut trousers Cameron Diaz and co. wore throughout the ’90s: almost straight leg, but with a subtle kick flare. The secret to making them feel ’90s as opposed to Noughties is in the waist–the celebs of the era were all about that mid-rise fit.

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Vince

tailored bootcut pants

Banana Republic

ponte ankle pants

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Jennifer Aniston and Brad Pitt shopping in Los Angeles, CA.November 23, 1999Bauer-Griffin

Cargo Pants

Go too sporty with your cargo pants and you run the risk of looking like a member of a Y2K girl band about to break into a choreographed dance routine. Instead, I like to look to Jennifer Aniston –and even her then boyfriend Brad Pitt–for pointers on how to do it the late ’90s way, with muted colors, laid-back tanks, and flip-flops (save the trainers for the gym).

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Citizens of Humanity

Marcelle cargo pants