The 30 Most Memorable Fashion Moments of the '90s

RIP platform sneakers.

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You've probably read at least one think-piece about the resurgence of the '90s, particularly in terms of fashion. The decade was a breeding ground for iconic clothing 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, sometimes cringeworthy, sometimes incredible fashion moments of the 1990s and the style stars that made them happen.

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Drew Barrymore (1990)

With her unique flower-child-meets-wild-child look, Barrymore 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. Here she is rocking a fanny pack covered in the word "fuck," because why not.

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Madonna (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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Alicia Silverstone (1990)

Before Clueless took the '90s fashion world by storm, introducing Cher Horowitz-plaid and an obsession with Alaïa, Alicia Silverstone's personal style could best be described by this laid-back look. The actress wore a pair of t-strap Mary Janes with a long skirt and slouchy sweater (because comfort is key, folks).

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Winona Ryder (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. Raven-colored hair and all-black red-carpet ensembles became her signatures.

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Winona Ryder and Johnny Depp (1991)

There's a reason the fashion world is still obsessed with Winona and Johnny's relationship today—the duo were the definition of gothic chic. The couple arrived hand-in-hand at the 48th Annual Golden Globe Awards in 1991 looking like they came straight from the set of a Tim Burton film.

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Courtney Love and Kurt Cobain (1991)

The king and queen of Seattle grunge, Kurt and Courtney were more or less the most influential couple of 1990s fashion. The Nirvana singer arguably started the entire grunge trend, with his mismatched, oversized outfits and shaggy mop of hair. Similarly, the Hole frontwoman was known for her torn, sheer slips, dark makeup, and babydoll dresses.

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Liv Tyler (1992)

Liv Tyler was the ultimate '90s babe—who could forget her role, alongside Alicia Silverstone, in the '93 video for Aerosmith's "Crazy?" In 1992, Tyler's wardrobe was filled-t0-the-brim with edgy dresses (like this one) and long skirts.

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Chloë Sevigny (1995)

Since her breakout role in the controversial cult film Kids, Chloë Sevigny has been 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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Sarah Jessica Parker (1995)

Two words: Carrie Bradshaw. We can't even begin to count how many trends Sarah Jessica Parker's character singlehandedly started in the late '90s, but many of the world's most well-known fashion brands (we're looking at you, Manolo Blahnik) owe her quite a bit of thanks. Here, three years before the premiere of Sex and the City, Parker preluded Bradshaw with this pink, feathery ensemble.

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Jennifer Aniston and Matthew Perry (1995)

It's impossible to conjure an image of the '90s without picturing the cast of Friends (and, in particular, Jennifer Aniston's now-famous Rachel haircut). In 1995, co-stars Aniston and Matthew Perry walked the 47th Annual Primetime Emmy Awards red carpet in ensembles that defined the decade: Aniston opted for a strapless, floor-length gown, complete with a pair of silky gloves, while Perry paired a classically '90s vest with an ill-fitting suit.

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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—body glitter.

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Johnny Depp and Kate Moss (1995)

Post Winona, Johnny took up with Kate Moss—a duo that became arguably as iconic as the gothic exes. In 1995, they arrived at a Los Angeles premiere looking the part of a high-fashion pair.

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Kate Moss and Johnny Depp (1995)

But Moss and Depp also shined style-wise off the red carpet—the couple dressed down in sleek coats and leather boots for the perfect combination of disheveled and chic.

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Sarah Jessica Parker (1995)

SJP arrived at the 49th Annual Tony Awards in 1995 in the '90s outfit of our dreams—a part-silky, part-sheer dress topped off with a pair of strappy, silver sandals.

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Brad Pitt and Gwyneth Paltrow (1996)

As one of the most beloved couples of the '90s, Brad and Gwyneth's relationship was well-documented until the pair parted ways in 1997. 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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Winona Ryder and Claire Danes (1996)

My So Called Life meets Heathers! Winona Ryder and Claire Danes debuted matching pixie cuts and badass dresses at the Los Angeles Fire and Ice Ball in 1996.

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Sarah Jessica Parker (1997)

If one thing is clear about the red carpet events of the '90s, it's that SJP had a knack for arriving in outfits that only she could pull off. Here, Parker wears an early version of "the naked dress" to the VH1 Vogue Fashion Awards.

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Mary-Kate and Ashley Olsen (1997)

Even though they were just a pair of tykes at the time, the Olsen twins were the epitome of '90s fashion. Exhibit A: The twins (epically) walked a red-carpet movie premiere in matching, tiny sunglasses and color-coordinating outfits.

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Nicole Kidman (1997)

The lace! The shawl! The hair! Nicole Kidman looked to be the belle of the ball in an epic ensemble at the American Film Institute Awards in Melbourne.

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Halle Berry (1998)

At the 50th Annual Primetime Emmy Awards in 1998, style icon Halle Berry walked the red carpet in a so-pretty, bejeweled gown and tiny sunglasses. It goes without saying that this outfit has definitely been recreated in recent years.

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Destiny's Child (1998)

It's no secret that the ladies of Destiny's Child had their outfits down. Here, the group posed in matching fabric at the The London Aquarium. If a photo like this doesn't make you want to start a girl group right this very second, you aren't looking close enough.

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Kirsten Dunst (1998)

Even before she owned the box office in the early aughts with classics like Bring It On and Spider-Man, Kirsten Dunst had a way of making an impression at events. In 1998, she attended the Eighth Annual Environmental Media Awards in Los Angeles wearing a strappy black-floral dress and Mary Janes (the shoe that you and the rest of the world owned multiple pairs of in the '90s).

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Jada Pinkett Smith (1998)

A pregnant Jada Pinkett Smith attended the Woo premiere in 1998 wearing the ultimate '90s 'fit: maternity addition. The actress paired an all-black jumpsuit with a sheer, button-down top. And what would a red carpet be without a pair of tiny sunglasses?

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Britney Spears (1999)

The late '90s ushered in an era of bubblegum pop, with Britney Spears leading the pack. Her sexy, belly-baring schoolgirl uniform in the video for "…Baby One More Time" paved the way for the low-slung jeans, navel rings, miniskirts, and bedazzled tank tops that would characterize the end of the decade's style.

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Naomi Campbell and Kate Moss (1999)

Supermodels Naomi Campbell and Kate Moss reigned Queens of the '90s Modeling World. They were spotted, towards the end of the decade, at the Versace Diamonds are Forever show in London wearing the coolest, slinkiest slip dresses.

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TLC (1999)

When TLC hit the scene, the music world went nuts—the drama! The music! The money! The girl gang defined their style with baggy athleisure pants, oversized tees and sweatshirts, and cropped tops. Their coordinating outfits epitomized an era of in-sync girl squads.

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Naomi Campbell (1999)

Towards the end of the decade, Campbell stunned at the UNICEF party in London—the model contrasted her vibrant dress and matching shoes with a bright-white bag.

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Gwen Stefani (1999)

The face of the SoCal ska-punk movement in the 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. Here she is perfecting the art of matching your hair with your shoes.

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Tyra Banks (1999)

At the 1999 ESPY Awards, supermodel and fashion icon Tyra Banks wore an ultra-coordinating look—her rose hair clips matched the floral print on her dress and shoes.

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Cameron Diaz (1999)

Cameron Diaz's outfit at the 56th Annual Golden Globe Awards in 1999 was so freaking '90s it hurts. The actress paired grungy eye makeup and crimped hair with a pant-dress combo and tiny purse.

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