Whoopi Goldberg

Event: 74th Academy Awards

Year: 2002

Est. Cost: $15,000*

Whoopi Goldberg’s choice of a lime green satin pantsuit for the 2002 Oscars raised many eyebrows. The outfit, designed by Chloé, was an odd choice for the red carpet and did not complement Whoopi’s figure or skin tone. The outfit’s fit and fabric made it one of the most expensive red carpet fails in history.