Charlize Theron

Event: 82nd Academy Awards

Year: 2010

Est. Cost: $8,000

Charlize Theron is known for her impeccable fashion sense, but the 2010 Oscars saw an unfortunate slip. She donned a custom-made gown by John Galliano, which many critics called a mess. Though the dress was estimated to cost around $8,000, it failed to impress.