Faith Hill

Event: 74th Academy Awards

Year: 2002

Est. Cost: $9,000*

Country singer Faith Hill’s rainbow-colored dress at the 2002 Oscars raised eyebrows. The Versace gown, which featured layers of bright pastel chiffon, was criticized for looking more like a prom dress than a red carpet-ensemble. The overly fluffy skirt and the ill-fitting bodice made it a fashion fail.