Her boyfriend Hugh Grant was the leading man of the moment, but Elizabeth Hurley stole the spotlight at the 1994 premiere of Four Weddings and a Funeral with her daring, safety-pinned black Versace dress.
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It was the catsuit seen ‘round the world. Jennifer Lopez gyrated in the new year wearing a nude, body-hugging outfit in the middle of Times Square. It left nothing to the imagination—except how the 41-year-old mother of twins is still so toned.
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Cher made an unforgettable appearance at the 1986 Oscars, showing up in a beaded Bob Mackie creation and flowing jet-black headdress.
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Oscar winner Geena Davis wore this see-through number at the 2000 Emmys and secured her place on many Worst Dressed of All-Time lists.
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Two years before she dared to go topless in Brokeback Mountain, Anne Hathaway wore a sheer blouse to the 2003 premiere of School of Rock.
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Alexander McQueen rarely makes a misstep, but his creation for Gwyneth Paltrow—an offshoot from his much-loved fall 2002 collection—was universally loathed by all viewers of the 74th Academy Awards. Her poor posture didn’t help, either.
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Not revealing so much as just plain weird, the Icelandic singer’s 2001 Oscar dress is still the go-to joke for red-carpet commentators every year. Designed by Marjan Pejoski, the swan frock was put to good use and auctioned off to benefit Oxfam four years later.
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The Kill Bill actress wore a gauzy Valentino dress to the 2007 Swarovski Fashion Rocks concert and revealed much more than the film’s famous yellow tracksuit allowed.
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Before Marc Anthony and “Bennifer,” there was P. Diddy—but even the bad-boy artist took a backseat to then-girlfriend Jennifer Lopez at the 2000 Grammy Awards. Ten years later, her oft-recreated jungle-print Versace dress is still one of the decade’s most memorable.
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Gossip Girl’s Serena van der Woodsen often steps out in barely there ensembles, and wore a plunging white blazer to a screening of her latest film The Private Lives of Pippa Lee in November 2009.
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She scooped up the Best Actress award for Funny Girl, and at the age of 26, young Babs walked onstage in playful see-through bellbottoms and a tunic by Scaasi.
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The Nine star nearly had a wardrobe malfunction at last year’s American Music Awards while wearing her short metallic dress.
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John Kerry’s filmmaker daughter turned heads in Cannes when walked the red carpet for Kill Bill 2 in 2004, proving black dresses and flash photography don’t mix.
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There’s a good reason the South Park creators attended the 2000 Academy Awards ceremony in dresses parodying Jennifer Lopez and Gwyneth Paltrow—they were on acid.
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