Restart slideshow

Hollywood's Most Daring Vintage Fashion Moments

Prev 18 of 29 Next
18. Bette Davis' Rebellion
In 1936, Bette Davis didn't believe she would win the Best Actress award she was nominated for, so she wore an old costume designed by Orry-Kelly to the ceremony as a protest. (For reference, he worked on films like Casablanca and Some Like It Hot.)

According to Vogue, she specifically chose a dress that looked like something the "hired help" might wear in protest of the contract she had with Warner Bros. that she wanted to be freed from. While she wasn't able to break her contract until 1939, her Oscar win that year became the first of five consecutive years that she would receive a nomination.

Months later, when she was asked by The Courier-Journal what she was doing with all of her statuettes, and she cheekily said she used them as door stoppers. "That's what Helen Hayes does with hers," she answered. "Keeps a door open with it. She's certainly solved the problem for me!"