6. 1955
Audrey Hepburn's boy cut and boy brows epitomize her sweet signature style — even more so than that updo and tiara from Breakfast at Tiffany's. We loved the Breakfast at Tiffany’s ‘do, of course, but that was a movie persona. This more relaxed, off-duty look is the one we associate more with the iconic star.

Who could forget that scene in Roman Holiday where she chopped all her hair off? She started a trend with that cropped ‘do with baby bangs, and we’re glad that she kept the short style offscreen.