Cher

Event: 60th Academy Awards

Year: 1988

Est. Cost: $20,000*

Cher has always been known for her bold and avant-garde fashion choices, but her outfit at the 1988 Oscars took things to a whole new level. Wearing a Bob Mackie creation, Cher’s outfit consisted of a black sequined two-piece set with a huge feathered headdress. While the ensemble was a perfect representation of Cher’s eclectic style, it was widely considered a fashion fail and too outlandish for the Oscars.