Tyra Banks

Event: 72nd Academy Awards

Year: 2000

Est. Cost: $12,000*

Supermodel Tyra Banks’s appearance at the 2000 Oscars left many fashion critics puzzled. The lilac gown with a voluminous skirt, designed by Vera Wang, was criticized for its excessive ruffles and unflattering proportions. The overly frilly design and the too-puffy skirt made it a red carpet fail to remember.