Gwyneth Paltrow

Event: 74th Academy Awards

Year: 2002

Est. Cost: $7,000*

Gwyneth Paltrow made her bold fashion statements at the 2002 Oscars in an Alexander McQueen gown that left many critics puzzled. The sheer black top paired with a full, multi-colored skirt was considered an unusual and unflattering combination. Although Paltrow is known for her impeccable fashion sense, this look remains a rare misstep in her red carpet history.