1Daryl Hannah
Darlene Hammond//Getty ImagesIn 1990, Hannah showed up to the Academy Awards wearing a fitted gold gown with an exaggerated mermaid hem, a white fur stole, elbow-length gloves, and a pair of matching glasses.
2Madonna
Ron Galella//Getty ImagesThe singer walked the 1991 Academy Awards red carpet dressed in a Bob Mackie-designed ensemble. Mackie custom-made the outfit for the songstress after they collaborated on a Vanity Fair cover.
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3Daryl Hannah
William Nation//Getty ImagesThe award-winning actor turned heads at the 1991 Academy Awards once again when she waltzed in wearing a sky-blue gown paired with a white scarf, blue-toned jewelry, and a pair of silver shades.
4Cindy Crawford
Ron Galella, Ltd.//Getty ImagesCrawford wore a striking black and white outfit, complete with a beret, to the 1992 Emmy Awards.
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5Geena Davis
Miranda Shen//Getty ImagesDavis’s red carpet fashion was truly something else in the ’90s. Case in point: the 1992 Academy Awards, where she wore a ruffled white dress that featured an asymmetrical hem.
6Drew Barrymore
Ron Galella, Ltd.//Getty ImagesThe tinted sunglasses, the Mickey Mouse bag, the jean jacket with contrast stitching—what's not to love about Barrymore’s laid back look? This outfit was for the 1993 premiere of the thriller Silver.
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7Claudia Schiffer
Ron Galella//Getty ImagesSchiffer looked pretty in pink while at the 1994 Academy Awards. Here, she’s seen posing next to her then-fiancée, the magician David Copperfield.
8Tyra Banks
Rose Hartman//Getty ImagesBanks wore a stunning silvery-blue spaghetti strap gown to the 1994 CFDA Awards.
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9Elizabeth Hurley
Dave Benett//Getty ImagesHurley wore a striking black Versace gown punctuated with oversized gold safety pins to the premiere of Four Weddings and a Funeral. Decades later, the dress remains one of the most talked-about red carpet looks.
10Naomi Campbell
Ron Galella//Getty ImagesCampbell, pictured here walking next to fellow supermodel Christy Turlington, rocked a white crochet mini-dress to attend the New York City red carpet premiere of Wolf.
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11Liv Tyler
Jeff Kravitz//Getty ImagesTyler chose a black dress with see-through sleeves for the 1995 MTV VMAs red carpet.
12Kate Moss
Kevin.Mazur//Getty ImagesMoss looked cool in all-black suiting while posing for the cameras at the 1995 VH1 Fashion and Music Awards.
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13Nicole Kidman
Steve Granitz//Getty ImagesKidman wore a sparkly silver dress to the 1995 premiere of Batman Forever.
14Drew Barrymore
Steve.Granitz//Getty ImagesBarrymore stunned in a silky baby blue minidress with a daisy hair clip at the Batman Forever red carpet. The young actor played Sugar in the Joel Schumacher-directed movie.
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15Halle Berry
Jim Smeal//Getty ImagesBerry wore a simple yet striking silver-blue gown to the 1995 People’s Choice Awards.
16Sharon Stone
Mitchell Gerber//Getty ImagesStone wore a gorgeous Vera Wang look (with pockets!) to attend the premiere of her movie Last Dance.
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17Oprah Winfrey
Barry King//Getty ImagesWinfrey was glowing at the 1995 Academy Awards dressed in a silky coffee-colored getup with a gold clutch and plenty of diamond accessories.
18Uma Thurman
Steve Granitz//Getty ImagesThurman kept it casual at the French Kiss premiere in a beige-colored suit with black accessories.
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19Mary J. Blige
Steve Granitz//Getty ImagesWho could forget Blige’s all-leopard print look that she wore at the Grammys?
20Kate Winslet
James Aylott//Getty ImagesWinslet sported a gorgeous pink Vivienne Westwood gown with a diamond necklace while attending the 1996 Oscars. She was nominated that year for Best Supporting Actress for her role in Sense and Sensibility.
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