Celine Dion

Event: Academy Awards

Year: 1999

Est. Cost: $25,000*

Celine Dion is known for her powerful voice and glamorous style, but her outfit at the 1999 Oscars was a miss. The singer wore a white Dior suit backward, with a fedora and sunglasses. Critics didn’t love the look, and it’s often cited as one of the most bizarre red carpet outfits of all time.