The 35 Most Memorable Fashion Moments of the '90s

RIP platform sneakers. ūüė•

Design by Katja Cho

You've probably read at least one think-piece about the resurgence of the '90s, and it really does seem like the decade was a breeding ground for iconic fashion styles that won't quit, from grunge-y flannel and cropped tops to slinky slip dresses. Ahead, join us on our trip down memory lane as we recount the most iconic fashion moments of the 1990s and the style stars that made them happen.

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Courtesy of Versace
The Supers (1990)

When the '90s began, the "supermodel" was born. Known as the Big Five, Cindy Crawford, Naomi Campbell, Christy Turlington, Tatjana Patitz, and Linda Evangelista (who famously said that she didn't get out of bed for less than $10,000 a day) ruled the runways and were celebrated for their unique personalities, beyond their otherworldly good looks. The iconic photographs that Peter Lindbergh shot of the supers in the early '90s are still widely used as editorial inspiration, and George Michael's "Freedom! '90" video, which features many of the women, is—in our humble opinion—still one of the greatest music videos ever made.

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Elaine from 'Seinfeld': Style Icon (1990)

The first episodes of Seinfeld aired around 1990 and kicked off a completely different era of television comedy courtesy of masterminds Larry David and Jerry Seinfeld. The show also had a lasting impact on fashion, with oversized floral dresses, fitted blazers, and loafers à la Elaine Benes making the rounds long after the show stopped airing.

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"Frank Micelotta/Hulton Archive"
Madonna's Cone Bra (1990)

Madonna is a fashion icon for the ages, but one of her most memorable (and most copied) signature looks was the cone bra that Jean Paul Gaultier designed for her Blond Ambition Tour in 1990.

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Everett Collection
'Beverly Hills, 90210' (1990)

Girls across America couldn't wait to try out the looks they saw on this '90s drama, which followed a group of stylish rich kids from Southern California who were basically living the teen dream. From Brenda's bangs and floral babydoll dresses to Donna's scrunchies and eccentric ensembles, fans would tune in to find and copy the biggest trends at Beverly Hills High.

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"Everett Collection"
Quirky TV Sweethearts (1991)

A group of spunky, young fashion icons emerged in the early '90s, giving girls everywhere the confidence to be themselves and wear whatever they want. Blossom Russo will forever be remembered for her hats, Clarissa Darling's mixed prints and oversize Keith Haring t-shirts are the stuff of legend, and Kelly Kapowski could pull off a crop top like no other. Other early '90s television style stars we remember fondly are Kelly Bundy of Married With Children and resident rich girl Lisa Turtle of Saved by the Bell.

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Ala√Įa's Fascination with Leopard (1991)

This collection that saw The Supers in head to toe leopard print is still considered one of Ala√Įa's most iconic collections ever. The looks were seductive, body-hugging, and many other staples of the show—off-the-shoulder looks and bondage-inspired pieces—have reared their heads again and again since.

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"Jeff Kravitz/FilmMagic, Inc"
Courtney Love and Kurt Cobain (1991)

The king and queen of Seattle grunge, Kurt and Courtney are arguably the most influential couple in 1990s fashion. The Hole frontwoman was known for her torn, sheer slips, dark makeup, and babydoll dresses, and is credited for popularizing the "kinderwhore" look that had a moment in the early '90s. Similarly, the Nirvana singer arguably started the entire grunge trend, with his mismatched, oversized outfits and shaggy mop of hair. We can't think of anyone in history who could make a flannel look so good, and with so little effort.

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"Ron Galella, Ltd."
Winona Ryder: Style Icon (1991)

Ryder was the ultimate '90s "It" Girl. In the early part of the decade, she scored a number of roles in cult-classic films, including Edward Scissorhands and Reality Bites, and her tomboyish style quickly caught the public's attention. Her raven pixie cut and all-black red-carpet ensembles became her signatures. Plus, it didn't hurt that she had Johnny Depp on her arm for a number of years. Say it with us: Winona forever.

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Baywatch (1991)

Pamela Anderson's strategically cut one-piece was the bathing suit that launched the buxom blonde to mainstream fame (at least, for those who hadn't followed her previous career in the pages of Playboy).

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'The Fresh Prince' Effect (1992)

Vibrant streetwear was an early '90s style staple. Will Smith became a bonafide trendsetter on The Fresh Prince of Bel Air with his colorful tracksuits, Zubaz pants, and impressive collection of Jordans. Hip-hop group TLC followed suit, and often performed in oversized t-shirts and mens' shorts, complete with cartoonish accessories in crazy colors.

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Condé Nast Archive/Corbis
Marc Jacobs for Perry Ellis Grunge Collection (1992)

In a career-defining moment, Jacobs (then the creative director at Perry Ellis) showed a grunge-inspired collection for spring/summer 1993 that promptly got him fired. The layered plaids, cashmere thermals, beanies, and Doc Martens that he sent down the runway were the staples of his generation, and they still resonate today. If you've never seen the show in full (and we really think you should), you can watch it right here.

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Calvin Klein
Kate Moss for Calvin Klein (1993)

In the early '90s, a waifish girl from London entered our lives and changed the fashion world forever. The polar opposite to the supermodels that reigned at the beginning of the decade, the teenage model ushered in the era of "heroin chic," which celebrated androgyny and incredibly slim figures. One of Moss' first campaigns was for Calvin Klein, in which she snuggled up with "Marky Mark," AKA Mark Walhberg, in nothing but her skivvies.

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Riot Grrrls (1993)

Kathleen Hanna's brand of loud feminist punk (via her wildly popular bands Bikini Kill and Le Tigre) became the poster child for the "riotgrrrl" movement of the '90s. Her signature slogan tees, cropped dresses, and combat boots were all part of the larger grunge trend of the era, but her brash, in-your-face attitude inspired a generation of young rebels, too.

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Raver Nation (1993)

The predecessor to the EDM explosion of today was the popular rave culture which migrated from Europe in the early '90s. Wide-leg JNCO jeans, armfuls of multicolored beaded bracelets called Kandi, and all rainbow everything characterized this scene, which still celebrates peace, love, unity, and respect.

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"Time & Life Pictures/ Time & Life Pictures"
Drew Barrymore: Style Icon (1993)

With her unique flower-child-meets-wild-child look, the actress was one of the decade's most badass style stars. She borrowed elements of grunge—dark makeup, choppy hair, tattoos—and mixed them with bohemian staples like daisy chains for a style that was all her own.

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Björk: Style Icon (1994)

Formerly of the Icelandic band The Sugarcubes, there never was ,nor will there ever be anything quite like Björk. Her genre-defying music its singular for its inventive beats and experimental turns, and her oddball style has been something to behold over the years (whether she's wearing a head full of teeny buns, Junya Watanabe or Maison Margiela, and yes, even in that giant swan dress).

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"Mark Seliger"
'My So-Called Life' (1994)

Angela Chase and her misfit friends gave a voice to all of the mid-'90s teens who felt like outsiders. Her oversized flannels and combat boots were characteristic of her unconfident character, and she won our hearts in the very first episode after dyeing her hair Crimson Glow, saying: "When Rayanne Graff told me my hair was holding me back I had to listen, because she wasn't just talking about my hair, she was talking about my life."

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"The Rachel" Haircut (1994)

On the early seasons of Friends, Jennifer Aniston's character Rachel Green became famous for her layered, choppy haircut, created by stylist Chris McMillan. It remains one of the most iconic hairstyles of all time, and was the most requested celebrity cut of the '90s.

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Gwyneth Paltrow and Brad Pitt's Red Carpet Reign (1994)

As one of the most beloved couples of the '90s, Brad and Gwyneth's relationship was well-documented until the pair parted ways. The duo was often photographed on the red carpet in coordinating outfits—and for a short period, matching haircuts—and their looks spanned the spectrum of '90s trends, from stark minimalism to grunge.

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RuPaul's MAC Campaign (1994)

RuPaul's provocative "I am the MAC girl" Viva Glam campaign marked the beginning of a franchise that still carries on today and made RuPaul the first drag supermodel.

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The X-Girl Fashion Show (1994)

Kim Gordon of Sonic Youth was one of downtown New York's coolest chicks in the '90s. In 1994, she and her partner staged a guerrilla fashion show for their streetwear label X-Girl on street during Fashion Week, around the corner from where their friend Marc Jacobs had just shown his collection. In attendance were some of the decade's biggest trendsetters, like Chloe Sevigny, Spike Jonze, and Sofia Coppola, who also launched her cult line of baby tees and dresses called Milkfed in the mid-'90s.

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"Time & Life Pictures"
The Spice Girls (1995)

A mid-'90s British invasion came in the form of five bubbly ladies in some seriously flashy outfits. The Spice Girls celebrated girl power and individuality: Scary, Baby, Ginger, Sporty, and Posh each contributed unique looks that young women all over the world admired. We can credit the Spice Girls with the popularity of platform shoes, pigtail buns, and—of course—lots of body glitter.

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"Tim Mosenfelder/Hulton Archive"
Gwen Stefani: Style Icon (1995)

The face of the SoCal ska-punk movement in the mid-'90s happened to be a bleached blonde ball of energy by the name of Gwen Stefani. The No Doubt frontwoman was known for her athletic build and style, often performing in nothing but cargo pants and a cropped beater, topped off with a bindi and a head full of tiny buns. Nearly two decades later, Stefani still has the best abs in the biz.

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Tom Ford's Gucci Revival (1995)

In 1994, Tom Ford became the creative director at Gucci after many years designing for the brand. He debuted a sexed-up, jet set-inspired collection for fall 1995, complete with a provocative ad campaign styled by Carine Roitfeld. This collection is credited with saving Gucci from imminent collapse—in the year after Ford's show, sales at Gucci increased by a whopping 90%.

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Alexander McQueen Highland Rape (1995)

McQueen's controversial Fall '95 show catapulted him to the heights of the fashion world and cemented his reputation as the industry's enfant terrible. "Highland Rape" featured disheveled models, violently torn clothing, screeching music, plus dirt and leaves strewn on the runway. While critics labeled this show, and many of his future shows, as degrading to women, McQueen maintained that it was a statement on Britain's cultural rape of Scotland in the 18th and 19th centuries.

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"Archive Pictures"
'Clueless' (1995)

Cher Horowitz, who singlehandedly taught the world the importance of Ala√Įa, will forever be one of the most celebrated style icons in film. Her revolving closet was something to aspire to, and many tried to replicate her preppy, matchy-matchy skirt suits and knee socks.

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"Warner Bros/Courtesy Everett Collection"
'Empire Records' (1995)

Liv Tyler was the ultimate '90s babe—who could forget her role, alongside Alicia Silverstone, in the '93 video for Aerosmith's "Crazy"?—and her look as Corey in this classic flick made her an instant icon. The cropped fuzzy sweater, plaid schoolgirl skirt, and lace-up combat boots that she made famous are now all wardrobe classics.

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Chlo√ę Sevigny : Style Icon (1995)

Since her breakout role in the controversial cult film Kids, Chlo√ę Sevigny became a "cool girl" beyond typical grunge queens and bubblegum pop girls. Known for her obsession with vintage and her playful take on fashion (she's considered one of the first true street style stars), she became the ingenue every designer wanted as their date at awards shows.

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"Columbia Pictures/courtesy Everett Co / Everett Collection"
'The Craft' (1996)

Fairuza Balk's character Nancy Downs was the poster child for the mid-'90s goth girl, with her black lipstick, witchy black dresses, crucifixes, and studded chokers. For those who didn't subscribe to the Cher Horowitz school of fashion, the ladies of The Craft provided an offbeat alternative. As Nancy proclaims in the movie, "We are the weirdos, mister."

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CANOVAS Alvaro/Contributor
Gianni Versace's Final Couture Show (1997)

Versace was one of the most influential fashion designers of his day, and he staged his final couture show—which many still consider one of his best—at the Ritz in Paris, barely a week before he was tragically murdered at his Miami home.

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