Katharine Hepburn
The multiple-Academy-Award-winning actress Katharine Hepburn was raised by progressive parents in Connecticut — her mother was a suffragette — and they gave her more than her signature New England mode of speech. Their tomboyish daughter, who got her start on the stage while in college at Bryn Mawr, was always an independent thinker. The modernity she embodied in real life eventually made its way into the characters she portrayed onstage and onscreen. But it wasn't just independence that made Hepburn modern: there were also the clothes. The famously feisty star showed the world that a woman could care about her looks and still look like herself. For a large portion of the 20th century, she stuck by wide-leg trousers, menswear-inspired shirts and comfortable shoes, even as girlier styles came in and out of fashion. The classic Katharine Hepburn look made masculine fashion chic. Throughout her life, she wore the pants.