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Taylor Swift’s 5 Most OUTRAGEOUS Looks

Far from "Shake It Off," Tay's most daring fashion has been under our noses this whole time!

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- Aug 21, 2014

The internet's been alight with discussion since Taylor Swift released her new video "Shake It Off," in which the pop star wears hip-hop inspired outfits and surrounds herself with twerking dancers. Two words: Total. Breakthrough. She's let go of her rep as a lily white pop star and given herself a bit of edge. She's showing us new sides of herself and her adorkable image. "Shaking it up," if you will!

She's the kind of artist who's never afraid to step outside the box, to be a little edgy, to give show people new sides of herself and her image. To "shake it up," if you will!

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Something that's gotten lost in all this, though, are all the occasions when Swift has literally worn blackface. It's become something of a hallmark through every stage of her career, from country upstart to chart-topping sensation. We've assembled some of T. Swift's wildest moments with this wild look; check it out below!

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"We Are Never Ever Getting Back Together." Unless "We" is Taylor and a can of black shoe polish!

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A timeless romance like the one in "Mine" can only be strengthened by daring fashion decisions.

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Her get-up wasn't limited to videos: here she is out on the town with former flame and One Direction-er Harry Styles. Do you think her controversial look contributed to their breakup? Or did it bring them together?

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How did everyone miss this? It's in the video that just came out!

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Yeah, you know what? This is actually kind of weird.

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