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The 51 Most Memorable Fashion Moments of the '90s

Kate Moss! Princess Diana! The Olsen twins!

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Looking back, the '90s feels like a golden era—the Game Boy! The Spice Girls! The last cell phone-less generation!—but most of all so when it comes to the fashion. Scrunchies, acid-wash jeans, tube tops and capri pants reigned supreme, along with crimped hair, Mary-Kate and Ashley Olsen, and punk rock. It was a glorious time, made only more glorious by the A-listers who blithely wore their '90s finest on the red carpet and out and about, secure in the knowledge that they would never have to look back on these iconic looks and feel anything other than pride. Unfortunately, in the year of our Lord 2020, these looks...hit a little different. So sit back, grab a packet of Pop Rocks, and instead of wondering how 1990 can be as far away from the present day as 205o (!), enjoy these looks, which represent the very best (if "best" is the right word here) of '90s fashion.

1998 MTV Video Music Awards
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Gwen Stefani

The singer was known for adding a little glamour to her punk rock looks in the '90s. Here, Stefani arrived to the 1998 MTV Video Music Awards in a fuzzy blue bikini top that matched her icy blue hair and...face jewels.

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Singer/rapper Lil'' Kim
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Lil' Kim

Always known for pushing the fashion envelope with her style, at 1999 MTV Video Music Awards, Lil' Kim hit the red carpet in an unforgettable boob-baring one-shoulder jumpsuit. The rapper finished off the look with a purple wig.

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London Fashion Week Designer Of The Year Awards At The Museum Of Natural History, Kate Moss, Naomi Campbell
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Kate Moss and Naomi Campbell

This model duo owned the '90s with their fashion. Moss and Campbell were spotted leaving a London Fashion Week event hand-in-hand in 1991, wearing their own renditions of school-girl-chic attire.

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Aaliyah at The Forum
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Aaliyah mastered streetwear long before the term became a fashion phenomenon, as evidenced by her Tommy Hilfiger yellow tracksuit in 1997. The singer was the poster child for the modern-day phrase "chill but still a big deal."

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Donatella Versace;Jennifer Lopez
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Dontalla Versace and Jennifer Lopez

Proof Dontalla Versace and J.Lo go way back. The two posed for the cameras while wearing some glitzy '90s fashion looks of sparkles and metallics.

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AT & T Presents City Kids Foundation Benefit
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Christy Turlington

The model casually out and about while rocking Versace. Iconic! We're getting Cher vibes, except Turlington's sheer top makes the outfit slightly more risqué than Alicia Silverstone's.

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Seventh Annual IFP/West Independent Spirit Awards
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Janet Jackson

This laidback but classic '90s look by the singer and actor can easily be recreated present day. The Poetic Justice star tucked a long-sleeved boatneck tee into a belted pair of mom jeans and wore a newsboy cap over her long box braids.

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Tony Bennet at the 38th Annual Grammy Awards in Los Angeles
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Mary J. Blige

In 1996, Mary J. Blige attended the Grammy Awards wearing a full leopard print ensemble with velvet gloves and dark sunglasses. It's safe to say this print will never go out of style. What a lewk.

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Michael Jackson;Madonna
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Madonna and Michael Jackson

Name a better duo than this King and Queen of Pop. In 1991, Madonna and Michael Jackson arrived to the 63rd Annual Academy Awards in the most glamorous Hollywood outfits. Madonna wore a glittery strapless gown, a fur stole, and Harry Winston jewelry while Michael went for a sequin cream blazer paired with his iconic gloves.

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47th Annual Golden Globe Awards - Arrivals
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Julia Roberts

That time Julia Roberts stunned in a suit and tie at the 1990 Golden Globe Awards. The actress had stunned in a variety of dresses in Pretty Woman (released in 1990!) but we love her in this oversize masculine suit just as much.

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Toni Braxton

It's hard to miss the singer's toned abs in this glittery two-piece ensemble in 1990. In fact, this classic-yet-sexy attire has been reworked over the years and celebrities are still loving two-piece skin-baring looks (exhibits A and B).

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Mariah Carey

Singer Mariah Carey stole the show at the 1997 MTV Video Music Awards by baring her abs in a bandeau top and showing off her legs in a high-slit skirt. Mimi's glamorous bombshell style has continued to serve as style inspo for decades to come.

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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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Tia and Tamera Mowry

If we were to name a more iconic duo than Mary-Kate and Ashley Olsen that would be Tia and Tamera Mowry. 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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Lisa Bonet

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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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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Frank Micelotta/Hulton ArchiveGetty Images

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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