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The 66 Most Memorable Fashion Moments of the '90s

I'd wear Princess Di's off-duty outfit today.

'90s fashion
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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 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.

california, united states   december 15  twin actresses mary kate and ashley olsen at the film premiere of anna and the king  photo by george dabrowskidmithe life picture collection via getty images
George Dabrowski
Mary-Kate and Ashley Olsen

No one did twinning better than these two. The Olsen sisters matched in black cardigans and fringe skirts at the movie premiere of Anna and the King in 1999.

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1997 cable ace awards
Jeff KravitzGetty Images
Angelina Jolie

The singer attended the 1997 Cable ACE Awards. Angie proved then and now that the slip dress is a classic piece to have in your wardrobe. Try styling it with a velvet cape.

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brad pitt and jennifer aniston file photos
Barry KingGetty Images
Jennifer Aniston and Brad Pitt

The only thing more memorable than Aniston's Rachel Green haircut/outfits was who she was dating at the time: Brad Pitt. We'll just leave this here.

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united states   march 18  vivica fox  photo by the life picture collection via getty images
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Vivica A. Fox

The actress hit all the '90s fashion benchmarks in this outfit: the purple bandanna, the see-through matching purple shirt, a skinny chain belt, and slightly flared jeans.

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united states   march 18  christina aguilera  photo by the life picture collection via getty images
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Christina Aguilera

The singer went for a head-to-toe gold look. Personally, we're getting Academy Award statue vibes.

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66th academy awards nominees luncheon
Ron GalellaGetty Images
Angela Bassett

The star and Janet Jackson dressed up in blazers to attend the 66th Academy Awards Nominees Luncheon in 1994. Bassett went with a bold fuchsia color while Jackson kept it classic in all white.

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second annual revlon's unforgettable women contest   winner annoucement
Ron Galella, Ltd.Getty Images
Cindy Crawford

The supermodel attended the Second Annual Revlon's Unforgettable Women Contest in 1990 at the MET in New York City. She wore a striking halter neck red dress nude tights and red heels. We're eyeing the sparkly diamonds on her neck and ears too.

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united states   march 19  melissa joan hart  photo by the life picture collection via getty images
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Melissa Joan Hart

Who grew up watching Sabrina the Teenage Witch? Here's the actress, circa 1990, in a genie-like costume, complete with a long braid.

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united states   march 06  halle berry  photo by the life picture collection via getty images
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Halle Berry

The star was a fan of rocking two pieces on the red carpet. She wore this flashy pink fringe outfit to the MTV Movie Awards in 1990.

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united states   march 18  jada pinkett  photo by the life picture collection via getty images
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Jada Pinkett Smith

Also in 1990, Jada Pinkett Smith debuted this shimmery green skirt and top set. We're getting mermaid vibes.

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brittany daniel, shane mcdermott, and sarah michelle gellar photo by ron galella, ltdron galella collection via getty images
Ron Galella, Ltd.
Sarah Michelle Gellar

We love a '90s matching moment. Here, Brittany Daniel, Shane McDermott, and Sarah Michelle Gellar coordinated outfits in a promotion for Swans Crossing in 1992.

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l r actresses reese witherspoon and selma blair at film premiere for cruel intentions  photo by dave alloccadmithe life picture collection via getty images
Dave Allocca
Reese Witherspoon and Selma Blair

It seemed like everyone owned a lace slip dress back in the '90s. Here, Blair wore one at the premiere of Cruel Intentions in 1999.

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oscar nominees night
Frank TrapperGetty Images
Natasha Richardson

The actress played one of the most stylish moms on TV in The Parent Trap and her fashion sense IRL was equally as good, as this blazer skirt (dress?) set proves.

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united states   march 18  mandy moore  photo by the life picture collection via getty images
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Mandy Moore

The actress and singer showed off a matching graphic set in 1990. We're taking bets on what the print is.

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opening of gianni versace's store linda evangelista
Ron GalellaGetty Images
Linda Evangelista

The '90s supermodel's crop blazer top and high-waisted pants is a look we still love today.

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1998 MTV Video Music Awards
Jim SmealGetty Images
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
Trevor GillespieGetty Images
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
Dave BenettGetty Images
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
Jeffrey MayerGetty Images

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
Marion CurtisGetty Images
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
Ron GalellaGetty Images
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
Ron Galella, Ltd.Getty Images
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
Ron GalellaGetty Images
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
David McGoughGetty Images
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
Ron Galella, Ltd.Getty Images
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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Clothing, Fashion, Crop top, Shirt, Dress, Shoulder, Suit, Formal wear, Event, Haute couture,
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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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Clothing, Dress, Leg, Red carpet, Little black dress, Thigh, Carpet, Fashion, Event, Long hair,
Victor MalafronteGetty Images
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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White, Clothing, Dress, Fashion, Shoulder, Cocktail dress, Beauty, Fashion model, Leg, Event,
Time & Life PicturesGetty Images
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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Fashion, Fashion design, Formal wear, Textile, Headgear, Event, Suit, Black hair, Fashion accessory, Costume,
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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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