Angelina Jolie

Event: 72nd Academy Awards

Year: 2000

Est. Cost: $5,000*

Angelina Jolie’s choice of outfit for the 2000 Oscars raised many eyebrows. The actress opted for a gothic-inspired Versace gown, complete with a floor-length cape and an abundance of black leather. Although Jolie won the Best Supporting Actress award that night, her fashion choice was met with mixed reviews, and the look remains one of the most memorable in Oscars history.