A fiercely private person who avoided press and public events, Katharine Hepburn’s aversion to “glamour” only made her that much more alluring. One of the early female adopters of trousers — she wore hers wide-legged and roomy — the actress liked to dress and live informally. Sporty and casual, she played tennis every morning and preferred to spend her days in menswear-inspired outfits like collared shirts and blazers instead of the tailored dresses popular at the time. Today, she is commonly referenced as a pioneer of the American sportswear aesthetic. Enjoy these highlights from her chic, comfortable wardrobe in our slideshow.