best: halle berry
To find a gown as beautiful as Halle Berry is a tall order. The actress won the Best Actress trophy at the 2002 Academy Awards for Monster's Ball in a wine-colored, discreetly nude, hand-painted and embroidered Elie Saab gown. Berry was so pleased by it that she chose to wear another dress from the Lebanese couturier to the Oscars the following year.
worst: lady gaga
It's not every day that someone would upstage a Jean Paul Gaultier dress with a gold-and-black feathered neck brace, but Lady Gaga proved she wasn't just anyone at the 2009 MTV Video Music Awards. Even her red carpet companion, Kermit the Frog, got whiplash from her fashion choices. "I'm just happy that it's not made out of someone I know," he quipped on MTV's pre-show.
worst: britney spears & justin timberlake
It was clear their romance was doomed when dating former Mickey Mouse Club stars Britney Spears and Justin Timberlake turned up for the 2001 American Music Awards in coordinated denim outfits. "They have things custom-made in denim with denim studs, denim tie-dye, dazzle denim," stylist Rachel Zoe revealed to People. Yes, and even country stars were laughing at them.
worst: tara reid
Don't you hate when this happens to you? When the strap of Tara Reid's dress slipped down on the red carpet of Sean "Diddy" Combs' birthday bash in New York City in 2004, her entire left breast was exposed to ecstatic photographers for a full 10 seconds while the oblivious party girl smiled. "I swear to you, I had no idea that had happened," she later told Access Hollywood.
best: julia roberts
Even if Julia Roberts (with then-boyfriend Benjamin Bratt) hadn't won the Best Actress Oscar for Erin Brockovich in 2001, she looked every bit the winner in the 1982 vintage Valentino black velvet gown she wore for the high-wattage Oscars ceremony. Roberts didn't employ a fashion stylist for the big night, but instead sought fashion advice of her then-10-year-old nieceEmma Roberts, who approved the dress.
worst: bjork
Quirky Icelandic singer and actress Bjork didn't mind ruffling a few feathers when she wore designer Marjan Pejoski's swan dress to the 2001 Academy Awards. Though most fashion critics hated the look, Bjork made the most of the attention by auctioning off the dress for charity
best: michelle williams
In a sea of the usual dark dresses at the 2006 Academy Awards, Best Supporting Actress nominee (for Brokeback Mountain) Michelle Williams stood out in her canary-yellow Vera Wang gown with a long train. The unusual color set off her luminous beauty, proved her star power and made everyone forget that she began her career on TV's Dawson's Creek.
worst: lara flynn boyle
Her ballerina costume not only offended the fashion police, but it emphasized just how scary-skinny actress Lara Flynn Boyle had become when she wore it to the Golden Globe Awards ceremony in 2003. "I eat pizza, I eat cookies. I'm fine," Lara insisted to People, defending her weight. "Everyone's a critic!"
worst: rose mcgowan
Future Charmed star Rose McGowan wore a see-through dress and a thong as she accompanied her then-fiancé Marilyn Manson to the 1998 MTV Video Music Awards. "I wore it to cause an uproar," she later admitted to Maxim magazine. "But I'll confess that I did change into another dress after walking up the red carpet. Those little strands in the back would have given me griddle butt if I'd sat down."
best: hilary swank
The lush midnight-blue color, high neck and deeply dipped back of Hilary Swank's Guy Laroche gown for the 2005 Academy Awards was elegant but boasted serious sex appeal. In an auditorium filled with strapless gowns, the Best Actress winner for Million Dollar Baby looked like a million bucks. "I thought it was really beautiful," she told the Associated Press about her flowing frock.
worst: celine dion
In 1999, the jaunty fedora and wacky reversed Dior suit Celine Dion wore to the Academy Awards landed her on several worst dressed lists. "In her backward tuxedo there's no way of knowing whether Diva Dion is coming or going: a profusion of confusion," the late fashion maven Mr. Blackwell sniped. But the singer took it in stride. "At the Oscars this year, I wanted to play a trick and wear the same suit forward," she told W magazine cheekily in 2007. "I did not."
worst: cher
When Cher wasn't nominated for her breakthrough performance in Mask, Cher took her revenge by asking designer Bob Mackie to create the skimpiest, most scandalous, Mohawk-inspired costume he could imagine for the 1986 ceremony, complete with a giant feathered headdress. "As you can see, I did receive my Academy Award booklet on how to dress like a serious actress," she teased when she took the stage as a presenter. Two years later, she won the Best Actress trophy for Moonstruck.
best: nicole kidman
Red-haired, porcelain-skinned actress Nicole Kidman finally moved out of her then-husband Tom Cruise's shadow when she wore a chartreuse John Galliano for Dior, Asian-inspired gown to the 1997 Oscars. The dress, along with her elegant hairstyle and understated makeup, established the future Oscar winner as an elegant fashion force to be reckoned with.
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