It was Marlene Detrich who flipped the sartorial script and began borrowing from the boys in the '30s. The German actress and singer took a shine to tuxedos and began performing in the bespoke style, topping the look off with a top hat. Suffice it say, it was controversial for the time.
Katharine Hepburn always had a sweet spot for menswear. At a time where androgynous dressing was widely unorthodox, she boldly refused to wear dresses in favor of trousers, which many thought to be morally wrong. Her menswear-inspired looks also happened to be as effortless as they were intrepid.