Demi Moore

In 1989, Demi Moore tried her hand at designing her own outfit for the 61st Academy Awards and let's just say she should've left it up to the pros. The top wasn't too bad with a fitted velvet bodice but the bottom half left people scratching their heads. It was a floor-length skirt but only covering the back. In the front, she sported cycling shorts, which stood out even more against the floral pattern on the inside of the skirt piece. Fortunately, her then-husband Bruce Willis kind of made up for it with his classic black tux. Photo: ©D.Hammond/Pictural Parade /KEYSTONE Canada

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