Dress of the Day: Katharine Hepburn in slacks. Today I feature a look rather than a design. The great actress Katharine Hepburn broke the mold in many ways, and sartorially speaking she shocked people by wearing slacks when they weren't considered appropriate public garb for a woman. This 1940s photo shows Kate in jacket, blouse, slacks, and flat shoes. A classic look, in large part thanks to her.