Women in film have been pushing gender boundaries with their outfits since the silent era, often breaking antiquated fashion rules. The pantsuit was introduced in the 1920s but wasn’t popularized until Marlene Dietrich wore one in her 1930 film Morocco. Greta Garbo sported a military-style trench coat in the 1928 film A Woman of Affairs, a look that endures to this day. These women set the stage for stars like Katharine Hepburn and Diane Keaton, who translated their personal styles onto the big screen and into our culture. These cinematic trailblazers continue to redefine and question the fashion rules.