Oscar Gowns: The 10 Most Iconic Dresses Ever!

1
Michelle Williams
Michelle Williams
Kate Durbin (Commentary)/ Hollywood.com
Who could forget this year’s My Week With Marilyn nominee, Michelle Williams, in a marigold dress by Vera Wang at the 2006 Oscars? Those red lips just may be why Michelle was cast to play Hollywood’s greatest icon, Marilyn Monroe.
2
Angelina Jolie
Angelina Jolie
Kate Durbin (Commentary)/ Hollywood.com
Angelina Jolie has worn many stunning Oscar gowns over the years, but we will never forget when she stunned us by showing up in all-black, Catwoman-like Versace at the 2000 Oscars. This was the same night she infamously kissed her brother on the lips.
3
Bjork
Bjork
Kate Durbin (Commentary)/ Hollywood.com
Bjork’s infamous Marjan Pejoski swan dress would look normal on today’s red carpet, what with Lady Gaga’s meat dress and Nicki Minaj’s pope accessory. In 2001, however, it was a truly avant garde statement—and a whole lot of (controversial) fun.
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4
Audrey Hepburn
Audrey Hepburn
Kate Durbin (Commentary)/ Hollywood.com
Audrey Hepburn’s graceful style has become worldwide iconic at this point, but in 1954 she wore an innocent yet beguiling floral Givenchy dress to pick up her Best Actress Oscar for Roman Holiday—and her fashion destiny was sealed.
5
Sharon Stone
Sharon Stone
Kate Durbin (Commentary)/ Hollywood.com
Sharon Stone used her basic fashion instincts to pair a sexy, unbuttoned white shirt with a blue silk secretary skirt at the 1996 Oscars. Her outfit was both irreverent and classic—just like Sharon.
6
Charlize Theron
Charlize Theron
Kate Durbin (Commentary)/ Hollywood.com
Charlize Theron wore a color and cut only she could dazzle in at the 2000 Oscars, in an opaque Orange Vera Wang gown with a plunging back.
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7
Gwyneth Paltrow
Gwyneth Paltrow
Kate Durbin (Commentary)/ Hollywood.com
In 1999 the world fell in love with Gwyneth Paltrow’s beautiful, romantic pink Ralph Lauren gown, which resembled the film she’d been nominated for, 'Shakespeare in Love.'
8
Halle Berry
Halle Berry
Kate Durbin (Commentary)/ Hollywood.com
Not only was Halle Berry the first African American actress to win an Oscar, in 2003 she trail-blazed the "naked dress" trend in her flower-grazed Elie Saab gown at the awards show.
9
Nicole Kidman
Nicole Kidman
Kate Durbin (Commentary)/ Hollywood.com
Nicole Kidman was a statuesque China doll in an green, oriental-printed Dior gown designed by John Galliano at the 1997 Oscars. With Tom Cruise by her side, she looked every bit the glamorous movie star.
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10
Matt Stone and Trey Parker
Matt Stone and Trey Parker
Kate Durbin (Commentary)/ Hollywood.com
South Park creators Matt Stone and Trey Parker dressed in drag at the 2000 Oscars. Matt’s gown looked similar to Gwyneth Paltrow’s pink Shakespeare in Love dress, while Parker’s resembled Jennifer Lopez's sexy green Versace gown. The two proved that no matter how seriously some might take the red carpet, the best fashion is all in good fun.

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