Diane Keaton

Event: 76th Academy Awards

Year: 2004

Est. Cost: $12,000*

Diane Keaton’s Ralph Lauren outfit at the 2004 Oscars was a departure from the glamorous gowns usually seen on the red carpet. The menswear-inspired ensemble consisted of a tuxedo, a bowler hat, and gloves. While the outfit was true to Keaton’s signature style, it was deemed inappropriate for the occasion and considered a red carpet fail.