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Hollywood's Most Daring Vintage Fashion Moments

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26. Demi Moore's Bike Shorts
Demi Moore liked to take fashion risks, and nothing proved that more true than her 1989 Academy Awards dress, which came complete with bicycle shorts and a long train.

She actually made the gown herself, creating the DIY out of spandex bike shorts, a corset, and metallic fabric. Even though Moore loved her creation, fashion pundits landed her on every worst dressed list for years after. But now that it has been over 30 years, people are starting to recognize its appeal.