Diane Keaton – 2004 Academy Awards
You’ve probably seen this one before. In 2004, legendary Hollywood actress Diane Keaton showed up at the Oscars wearing a classic Ralph Lauren suit that was (we assume) initially designed to be used by men. The backlash was intense at the time, with Keaton making it to virtually all of the worst-dressed lists.
Looking back, though, it’s hard to pinpoint exactly why. If you ignore the fact most female celebs don’t wear suits on the red carpet, Keaton actually looks pretty good. And in a day and age where gender norms are becoming obsolete, it’s fair to say this is a look that was ahead of its time.