1. Grace Kelly, 1955
It may not seem much by today’s standards, but the aquamarine silk column dress worn by Grace Kelly to accept her Best Actress gong at the 1955 ceremony set the bar for expensive Oscar dresses. Designed by Edith Head, Grace had actually already worn the simple gown a year earlier at the New York premiere of The Country Girl. It goes down as one of the most-loved Oscar looks in history.