27 Iconic Outfits From The ’90s That Will Go Down In Fashion History

The ’90s can be a breeding ground for some divisive looks: whale tails, butterfly clips, and capri pants. But it was also a golden age of fashion, IMHO.

Icons of the decade – like Jennifer Aniston, Halle Berry and Winona Ryder – all had major style moments on the red carpet, rocking minimalist, glam and goth chic looks, respectively. A young Kate Moss was photographed in a nude dress that changed the trajectory of sheer ‘fit’ forever and helped make it one of today’s most enduring trends.

Perhaps most iconic of all was Princess Diana, whose style legacy is as celebrated as her life – even today. When she debuted her “Revenge Dress” in 1997, she not only got her enduring nickname — I’d argue it’s now officially part of the stages of grief — denial, anger, bargaining, depression, acceptance, and revenge. Dress .

I’m not alone in yearning for the ‘fit of the last decade’. Some of today’s most stylish celebs are dipping into the fashion archives on a frequent (if not daily) basis for vintage dresses. Dua Lipa recently rocked a 1992 Chanel creation at the Met Gala, while Zendaya often looks to the ’90s Prada archives for her red-carpet appearances. Even Kendall Jenner and Kim Kardashian, among their other stylish siblings, are rocking items from the vaults, wearing vintage Jean Paul Gaultier.

If you too want to take a walk down the memory lane and remember the fits who graced the era, read on. I have 25 for you.

Britney Spears

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In 1999, before Britney Spears was dubbed the “Princess of Pop,” she first appeared at the Teen Choice Awards wearing a baby pink tank and matching pants, accessorized with metallic pink plates. Q: “I’m not a girl, not a woman yet.”

Jennifer Lopez

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on the heels of his film selena (pre-“Jenny From The Block”), Jennifer Lopez wore a cowl-neck chainmail crop top and a leather maxi to the 1998 MTV Movie Awards – her most ‘fitted’ yet.

Princess Diana

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This Princess Di dress from 1997 was iconic for two major reasons: One, it’s capital-S stunning. More importantly, she wore this too-funny outfit for the royals very same The night now-King Charles publicly confessed his infidelity, marking the official origin of the “Revenge Dress”.

lil’ kim

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One of the most iconic fashion moments of the 1990s, Lil’ Kim’s mermaid-inspired, one-shoulder look (complete with shell-shaped nipple paste) is still going tough — even in 2023.

Kate Moss

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Julia Roberts

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Julia Roberts has been known to rock an oversized pantsuit on the red carpet, yes. But the skirt suit she wore to the 1992 Golden Globes was especially chic. Paired with her perfectly messy bob, and gold hoops, she looked every bit the star.

Jada Pinkett Smith

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TBH, I could see just about any style star wearing Jada Pinkett Smith’s shimmery, chainmail crop top and maxi skirt at the 1997 Oscars after party. It’s a look worth copying for sure.

drew barrymore

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micro bangs are already difficult to remove And A chevron print (the one now frowned upon in “Cheugy” purgatory)—together, and so much more. But it ‘fits Drew Barrymore Work,

Angelina Jolie

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before that infamous leg pop at the oscars, there was This Standout moment at a different award show: A spicy halter dress studded with crystals at the 1999 Golden Globes. She won the Best Performance by an Actress award, BTW.

destiny’s Child

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Just your regularly scheduled reminder that Beyoncé can do no wrong – in the fashion department or otherwise. She, Michelle Williams and Kelly Rowland served up all leather cut-outs in 1998. It was just one of many incredible (coordinating!) looks they’d serve up during their tenure.

Gwyneth Paltrow

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Gwyneth Paltrow definitely had a winner at the 1999 Oscars — as the recipient of the Best Actress award for her turn Shakespeare in Love (And for rocking the red carpet in this blush pink ball gown).

sarah jessica parker

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Sarah Jessica Parker didn’t just take a page out of Carrie Bradshaw’s playbook, she pulled an entire dress out of her wardrobe. There was an uproar after she wore a “naked outfit” with Mr. Big on Season 1 of satcParker wore a mini slip IRL to attend VH1 the trend Fashion Awards in 1997.

Spice Girls

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Let’s be real: The Spice Girls defined a style era in the ’90s. But her appearance at the 1997 MTV VMAs — complete with platform sneakers, leopard print, and athleisure staples to boot — was total group slaying.

Jennifer Aniston

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There were almost too many Jennifer Aniston options to choose from, since she’s basically the IRL version of her stylish on-screen persona, Rachel Green. But Friend The star may have been most radiant in this sculpted brown number at the 1999 Emmy Awards. Shiny embellished top, sleek skirt, messy hair? Before Vibes, Vibes was called ‘Vibes’.

diane keaton

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Diane Keaton has been a style icon for decades, constantly rocking her suit. But this all-white ‘fit at the 1997 Academy Awards went way beyond your usual purview of chic. With her styling touches – glasses, choker, gloves and platform boots – she also completely nailed the look His,

Audrey Hepburn

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Before barbicore, there was Audrey Hepburn. I have no words for this one-shoulder vibrant pink number the actress wore to the 1992 Oscars. Just wow


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Aaliyah Had the Best Street Style Game, But No ‘Fit’ Ever Eclipsed This White-Hot Look Anastasia Premiere in 1997. With white sneaks, a faux fur coat, and her signature crop top, she looked wintry cool.

Cindy Crawford

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Cindy Crawford was a style icon of the 1990s and this saucy gown — for her Oscars date with Richard Gere, no less — is unquestionably one of her best looks of the decade. just fire

Winona Ryder

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Winona Ryder was all about grunge glam in the ’90s. But she traded in her all-black ‘fit for an ivory, beaded, flapper-style number to attend the Academy Awards in 1994. With those pointy pumps? How good.

mariah carey and whitney houston

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Diva history was made when Mariah Carey and Whitney Houston linked up at the 1998 MTV Video Music Awards. In fact, it was so iconic Dua Lipa and Meghan The Stallion pay tribute through this Too Seen at last year’s Grammys wearing matching Versace.

Halle Berry

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Let’s get this straight: Halle Berry can do no wrong with an outfit. But this boudoir-inspired slip dress with sheer lace panels was perhaps her best effortlessly spicy look.

britney spears (again)

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OK, but this metallic pink bandeau top and white pants Britney Spears fit to perform at a 1999 concert is part of the Spears fashion canon.

Kate Hudson

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The white and gold number that Kate Hudson wore to attend the 1999 MTV Movie Awards was equal parts angelic and daring — and totally ’90s.

Kate Winslet

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TitanicK ran everyday so Kate Winslet could run. She attended the 1998 Academy Awards in this regal gown, complete with intricate embroidery reminiscent of her on-screen character’s elaborate wardrobe.

mother of jesus

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In 1991, Madonna channeled Marilyn Monroe In a sparkly strapless number and fur stole. He Wearing $20 million worth of Harry Winston bling, for a look that will be recreated for decades to come.

meg ryan

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There’s something about Meg Ryan walking the red carpet in a fur-trimmed, zesty lime green coat that makes me wish I had a time machine…

cameron diaz

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Cameron Diaz Served Up the ’90s—Donning Everything From Minimalist Slips preppy’ fits, The flutter sleeves and lone clip’s saccharine vibes perfectly capture her then-current status as a rom-com darling.

Nicole Kidman

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In case you needed proof that Nicole Kidman has always been a must-watch on the red carpet, here’s a gorgeously embroidered chartreuse beauty that’s swaying. Paired with a beaded bag, drop earrings, and edgy sky-blue slingback, the look was a gem.

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