The 39 Most Memorable Fashion Moments of the '90s

Kate Moss! Princess Diana! The Olsen twins!

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You've probably read at least one think-piece about the resurgence of the '90s, particularly in terms of its 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.

Fran Drescher
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Fran Drescher

If you've never seen The Nanny, I don't know you. Fran Drescher's outfits on the show, which included teeny-tiny sweaters and body-hugging miniskirts, were iconic looks. Drescher's real life style was a little more toned-down glamorous, like this white halter-neck dress though she did find ways to jazz things up (see: her floral head piece).

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Mandy Moore
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Mandy Moore

Before her A Walk to Remember Days, Mandy Moore was an established singer (remember "Candy?") and definitely a '90s gal. Her style was defined by simple tank tops and bottoms with a thin chain belt running across. This photo is peak '90s.

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Tia and Tamara Mowrey

If we were to name a more iconic duo than Mary-Kate and Ashley Olsen that would be Tia and Tamara Mowrey. The twins were the stars of Sister, Sister and their closets (both on the show and off) were amazingly good. Think everything from covetable denim overalls and bucket hats to these mini shift dresses with the scarves (!!). Someone bring back these exact looks on the runway, please.

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Let this photo of Lisa Bonet in the '90s be proof that her daughter Zoë Kravitz is the spitting image of her. In addition to being a sought-after actress during that time, Bonet was known for her free-spirited, bohemian style. Her outfits, like the one on the left, were an expression of her artistic perspective.

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Tom Cruise and Nicole Kidman Sighting in Los Angeles in 1990
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Nicole Kidman and Tom Cruise

The two took couple matching to the next level when they were spotted in Los Angeles wearing white button-down shirts and jeans.

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Drew Barrymore

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

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

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 as laid-back. 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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Chloë Sevigny

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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Winona Ryder

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

Yes, Ryder was a style star on her own. But 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

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

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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Diana At Serpentine
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Princess Diana

Princess Di wore this daring LBD the same night Prince Charles' tell-all interview about their life came out. It was dubbed the "revenge dress" because the princess didn't let anyone, or anything, hold her down from shining that night. The off-the-shoulder design and asymmetrical hemline made a major style statement and is one of the most iconic looks of British royalty to date.

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Grant And Hurley
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Elizabeth Hurley and Hugh Grant

The couple arrived to the post-premiere party of Grant's film, Four Weddings and a Funeral in London. Hurley left her style mark that night in this iconic Versace pin dress. Since then many celebrities have tried this look, including Irina Shayk at the 2018 Cannes Film Festival.

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In memory of Diana, Princess of Wales, who was killed in an automobile accident in Paris, France on August 31, 1997.
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Princess Diana

Another iconic look from Princess Di. (Hailey Bieber even recreated this casual outfit for British Vogue). She was ahead of her time in adopting the biker shorts and oversized pullover trend, which has just now taken over the fashion world.

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The 47th Annual Emmy Awards - Press Room
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Katie Holmes and James Van Der Beek

Dawson's Creek fans will love this throwback moment from its two cast members at the 47th Annual Emmy Awards. Van Der Beek looked dapper in a suit while Holmes rocked that square neckline gown (that style is now back in fashion) with a ball-shaped floral bag (also back in fashion).

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Sarah Jessica Parker

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

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

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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Halle Berry

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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Johnny Depp and Kate Moss

Post-Winona, Depp 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

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

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

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 to preppy chic.

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Winona Ryder and Claire Danes

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

If one thing is clear about 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

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 monochromatic outfits.

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Nicole Kidman

The lace! The shawl! The hair! Nicole Kidman looked to be the belle of the ball in an epic '90s look at the American Film Institute Awards in Melbourne.

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Destiny's Child

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

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 8th 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 probably owned multiple pairs of in the '90s).

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Jada Pinkett Smith

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

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

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

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

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

The face of the SoCal ska-punk movement happened to be a 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

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

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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