Anne Hathaway

Event: 85th Academy Awards

Year: 2013

Est. Cost: $10,000*

Anne Hathaway’s 2013 Oscars dress became one of the most talked-about fashion moments of the year for all the wrong reasons. The blush pink Prada gown, while elegant in its simplicity, drew criticism for the awkwardly placed seams at the bust. Despite the controversy, Hathaway still managed to take home the Oscar for Best Supporting Actress.