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The 75 Most Daring Dresses Celebrities Have Ever Worn

Grace Jones.

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Back in 1989, actress Grace Jones decided that clothes were a cage and went out semi-nude in this outfit, which… strongly resembles a cage.

Christina Aguilera (again).

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Man, the “Xtina” period of Christina Aguilera’s career lead the singer to some wild outfits, including this one from 2002 where she seemingly just grabbed a sheer cloth and wrapped it around her chest real quick.

Lara Flynn Boyle

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If you don’t think Lara Flynn Boyle is daring to come right from a ballet lesson to the Golden Globes, you’ve never showed up to a fancy party in sweatpants because no one told you it was formal attire.

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