The 75 Most Daring Dresses Celebrities Have Ever Worn

CeeLo green.

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Again, another dress that does not show off skin, but does show off the deep, inner psyche of the person wearing it.

Matt Stone and Trey Parker.

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South Park creators Matt Stone and Trey Parker donned Jennifer Lopez’s and Gwyneth Paltrow’s most famous dresses for the 2000 Oscars. And damn if they don’t pull them off.

Angelina Jolie.

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 This is it — the famous slit from the 2012 Oscars. Although, after some of the dresses we’ve seen here today, a single leg doesn’t seem so revealing. Why is this dress so famous?

I wonder if Angelina was pushing boundaries here that we couldn’t see. Maybe she had a vial of Billy Bob Thorton’s blood tucked into her dress too.

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