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The 75 Most Daring Dresses Celebrities Have Ever Worn

Christina Aguilera.

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 Showing up for the Blockbuster Entertainment Awards in 2002, it looks like Christina Aguilera took a dress and cut a bunch of slits out of it?

Maybe it snagged on a protruding nail and caused on rip, and Christina had to cut a bunch more rips into it to make it look intentional?

Macy Gray

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How gutsy do you have to be to turn a red carpet walk into an advertisement? I mean, all red carpet walks are kind of advertisements, but back in 2001, Macy Gray decided to be overt about it.

Pink.

via: Getty Images

It looks as though Pink used the 2000 Video Music Awards as an opportunity to wear pants into which she had cut deep plunging… well, not necklines. Hiplines?.

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