It’s hard to believe, but the granddaddy of all red carpet events – THE ACADEMY AWARDS! – is only two days away. Can you tell we’re excited? Really, we are. Obviously, our favorite part of the entire evening is the arrivals: Who’s there, and more importantly, who they’re wearing. Above all, we want to see who’s bold enough to take the fashion risks – because those are the dresses we’ll be talking about the next morning. And those who really make a mark could end up on a list like this one in twenty years time!

Behold, our choices for the fifteen riskiest red carpet Oscar looks of all time. Some are great, some… not so much. But the best ones are an amazing combination of both. Read on as we take a look back at some of the most fashionably daring dames on Hollywood’s biggest night.

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