1An Red Carpet Updo on Gwyneth Paltrow
Evan Agostini//Getty ImagesTaken just a few years before actress Gwyneth Paltrow won an Oscar for Shakespeare in Love, but she was already ruling the red carpet. The updo feels unfussy in the best way possible—face-framing tendrils, imperfect bun—and can easily be recreated on your own.
2Cindy Crawford's Signature Red Carpet Curls
Ron Galella, Ltd.//Getty ImagesSupermodel Cindy Crawford’s signature look—big, blown-out hair—doesn’t actually scream ‘90s—instead, it feels timeless. But Marjan reminds us this is the “iconic blowout” of the era. You can easily DIY with hot rollers.
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3Jennifer Lopez’s Messy Bun
Jeff Kravitz//Getty ImagesBack then, she was just Jenny from the Block. And her messy bun, finished off by some hair clips. If you don’t have the hair texture to get this look on your own, may we suggest another icon of the ’90s, a crimper?
4A Flipped Out Lob on Tyra Banks
Daniel Simon//Getty ImagesBefore she was the host and lead judge of “America’s Next Top Model,” Tyra Banksruledg the runways. Her flipped-out long bob is teased at the crown for extra volume.
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5Bold Buns on Gwen Stefani
Jim Smeal//Getty ImagesWhen No Doubt dropped their first album, “Tragic Kingdom,” in 1995, it started a beauty revolution. Lead singer Gwen Stefani’s blue raspberry bob and penchant for complex hairstyles (braids and buns, wet sets) set a mood. Modern admirers know to skip the culturally appropriative bindi.
6Naomi Campbell’s Voluminous Blowout
Gene Shaw//Getty ImagesA simple, voluminous blowout was supermodel Naomi Campbell’s signature look through the ’90s. The look is actually easier to get than you’d think, and we have details here.
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7Winona Ryder’s Delicate Pixie and Baby Bangs
Ron Galella, Ltd.//Getty ImagesThe’90s were Winona’s world and we were just living in it. This pixie was chopped by mononym hairstyling legend Garren, who gave her delicate baby bangs to match the short chop.
8Kirsten Dunst’s Butterfly Clips and Updo
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9Linda Evangelista’s Flipped Out Bob
Pool ARNAL/PAT//Getty ImagesSupermodel and hair chameleon Linda Evangelista tried it all in the ’90s—baby bangs, bleach blonde pixie, fire engine red bob—and her natural brown hue in a flipped-out bob.
10Brandy’s Gorgeous Braids
Michael Ochs Archives//Getty ImagesOur patron saint of box braids. Brandy got her start in the ’90s with a huge television career and a popular eponymous pop-R&B album.
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11Kate Moss’s Signature Beauty Look
Jim Smeal//Getty ImagesPerhaps the biggest It Girl of the ’90s, Kate Moss’s signature look of golden hair and long layers is still going strong over 30 years later.
12Undone Waves on Penelope Cruz
Jim Smeal//Getty ImagesTo get Penelope Cruz’s undone waves, try a salt spray or sleep with it braided.
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13Brittany Murphy’s Flippy Bob
Ron Galella, Ltd.//Getty ImagesTo get the late Brittany Murphy’s signature look of the era (which is also very Mary J. Blige), you need piecey layers and a good roll of the wrist.
14Christina Aguilera’s Crimped Curls
Chris Walter//Getty ImagesA crimper again?! You know it. To get all the volume at your roots just like Christina Aguilera, position the crimper as close to your scalp as possible.
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15Drew Barrymore’s Bleached Daisy 'Do
Steve.Granitz//Getty Images 16Demi Moore’s Short Curls and Beret
Kypros//Getty ImagesBefore she shaved her head for 1997’s G.I. Jane, actress Demi Moore kept her dark hair short and accessorized with pieces like this burgundy beret.
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17Alicia Silverstone’s Cher Hairstyles
CBS Photo Archive//Getty ImagesValley Girl blonde took over America after Alicia Silverstone starred in 1995’s Clueless.
18Julia Roberts’ Natural Texture
Barry King//Getty ImagesJulia Roberts’ smile isn’t the only thing she’s known for... just look at those curls. Her signature red and natural texture made her eternally red carpet-ready.
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19Tatyana Ali’s Bucket Hat
Michael Ochs Archives//Getty ImagesKnown for her role as Will Smith’s youngest cousin Ashley Banks on Fresh Prince of Bel Air, Tatyana Ali’s bucket hat was an accessory of the moment.
20Uma Thurman’s Easy Breezy Signature Look
Ron Galella//Getty ImagesUma Thurman’s look was simple—below the chin layers and a slightly off-center part—but perfection.
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