The '90s Offer All the Outfit Inspiration You Need Right Now (2024)

Big Ol' Baggy Jeans

Pooling, wide-leg jeans—the kind gloriously offbeat dressers like Justin Bieber and Pete Davidson swear by today—remain a calling card of Y2K-era fashion, but the cut first took off in the decade that preceded it.

Rev Run-Approved Tracksuits

‘70s-indebted tracksuits—crisp, understated, best paired with a thicket of unkempt chest hair—might be all the rage right now, but the ones we’re talking about here are cut from a different cloth entirely. Comfortable, crinkly, and usually made from a lightweight nylon blend, they hearken back to a time when hip-hop luminaries like Run-D.M.C were on the cusp of becoming the world’s biggest influencers—Adidas shell-toes, swishy pants, and all.

MTV-Ready Flannel Shirts

Flannel shirts weren’t invented in the ‘90s, but their association with the era’s grunge scene forever lends them an aura of counter-cultural cool. Layer one over a hoodie or a long-sleeve T-shirt and accent with a healthy dose of stick-it-to-the-man ‘tude.

Red Carpet-Worthy Bucket Hats

The ‘90s were a downright wild time. ‘90s fashion? Even wilder. How else to explain the mind-boggling array of bucket hats on display, perched precariously on the heads of A-listers (with very relaxed notion of conventional dress codes) step-and-repeating their way through a decade's worth of premieres? Turns out, all those newly-heralded style icons were onto something.

This-Is-How-You-Win Leather Blazers

Leather was everywhere in the ‘90s—on vests, pants, knee-length trenches—but no supple cowhide piece looks cooler today than the leather blazer. Throw one on with aturtleneck and tinted shades to kick the sleaze factor up a notch—and imbue your ‘90s-inspired get-ups with a little stylistic verve borrowed from the decades before it.

Spotlight-Stealing Necklaces

Take it from Tommy Lee: Nothing transforms a plain Jane tank top and blue jeans into a rockstar-level look more efficiently than neckful of chunky-as-hell jewelry.

Shredded Cardigans

When Nirvana showed up to perform onMTV Unplugged in 1993, they probably didn’t know it would be one of their last performances with the late, great Kurt Cobain at the helm—or that his outfit would make menswear history in the process. Cobain’s shaggy cardigan became so indelibly lodged in the pop culture consciousness that it sold for over $300,000 dollars at auction just a few years ago, solidifying its status as a defining emblem of ‘90s style. Almost three decades later, the Nirvana frontman's entire look still feels fresh—start with a punkish sweater, layer on a graphic tee, and finish with light wash jeans.

Slick Black Derbies

Sneakers became bona fide status symbols in the ‘90s—thanks, in part, to the dominance of Michael Jordan—but chunky derbies were the alternative shoe of choice for everyone from prepsters to punks. Today, the derby’s spectrum-spanning appeal hasn’t lost an ounce of its luster. (Naturally, they also tend to look killer with some '90s-inspired jeans.) The trick is to treat them like anything but a precious grail: buy 'em in black, and don’t be afraid to beat those sturdy soles into the ground.

Y2K-Adjacent Shades

Classic aviators are cool and all, but the sporty wraparound frames favored by ‘90 badasses fictional (Christopher Moltisanti) and not (Dennis Rodman) speak to a time when a bright new future was on everyone's mind. Whether you're nostalgic for the days before Twitter or simply looking to channel one of the decade's stylish rebels, shades like these are an easy way to switch up your entire vibe with one move.