Gwen! Aaliyah! Cindy! 10 Women Who Became Denim Style Icons Inline
Photo: Getty Images1/20Gwen Stefani
Anyone who grew up in the ’90s and early ’00s can’t forget Stefani’s infamous crop trops (and abs). Twenty years later, that decade feels fresh again—and getting her denim look is as simple as investing in a pair of embellished boyfriend jeans.
Photo: (From left) Courtesy of farfetch.com; Courtesy of modaoperandi.com2/20Tu Es Mon Trésor pearl-embellished boyfriend jeans, $863, farfetch; MSGM paint-splattered jeans, $330, modaoperandi.com
Photo: Getty Images3/20Lauren Hutton
It’s only natural that an all-American beauty would look so good in head-to-toe, true-blue denim. A matching cap would put your slouchy jacket and jeans over the top.
Photo: (All) Courtesy of agjeans.com4/20AG Robyn jacket in 17 Years Folklore, $275, and The Phoebe in 18 Years Oasis, $245, for information: agjeans.com
Photo: Getty Images5/20TLC
It was 1992 when the TLC trio originally pinned condoms to their overalls, and yet we’re still talking about it 23 years later. To pull off this style, we say the baggier, the better.

Photo: Getty Images7/20Cher
If you were Cher in 1988, faded, embroidered jeans looked appropriate even on the American Music Awards red carpet.
Photo: (From left) Courtesy of shopbop.com; Courtesy of Otte NY8/20Paige Denim Jimmy Jimmy skinny jeans, $359, shopbop.com; The Great The Mister Slouch boyfriend jeans, $375, for information: otteny.com
Photo: Getty Images9/20Jane Birkin
Ask any fashion editor to name her style muse and Jane Birkin will likely rank high on her list. Birkin’s super flares and button-up look just as cool and modern today.
Photo: (From left) Courtesy of hudsonjeans.com; Courtesy of mih-jeans.com10/20Hudson Jeans Jodi high-waist flare in slater, $225, for information: hudsonjeans.com; MiH Jeans The Principle super-flare jeans, $255, for information: mih-jeans.com
Photo: Getty Images11/20Destiny's Child
What’s more ’90s than a denim bikini? Destiny’s Child styled theirs with cutoff shorts.
Photo: (All) Courtesy of ellesasson.com12/20Elle Sasson Adelle top, $270, and Belle skirt, $325, for information: ellesasson.com
Photo: Getty Images13/20Cindy Crawford
As one of the most famous models in the country, it was fitting that Cindy Crawford wore her jeans in a classic, all-American way. Paired with a leotard, boot-cut jeans are as simple and chic as it gets.

Photo: Getty Images15/20Aaliyah
While everyone else was going overboard with logos in the ’90s, Aaliyah routinely wore simple, sexy pieces like this denim jumpsuit.
Photo: (From left) Courtesy of Guess16/20Guess jean jumpsuit, price upon request
For information: guess.com
Photo: Getty Images17/20Chloë Sevigny
The ultimate It girl, Chloë Sevigny is making us rethink suspenders—and cuffed blue stovepipes.
Photo: (From left) Courtesy of True Religion18/20True Religion jeans, $228
For information: truereligion.com
Photo: Everett Collection19/20Audrey Hepburn
No one made straight-leg, no-fuss Wranglers look more adorably enticing than Audrey Hepburn, who added a cherry-red sweater and headband to hers.
Photo: (From left) Courtesy of Wrangler20/20Wrangler prewashed cowboy-cut slim-fit jeans, $35