“I put on pants 50 years ago and declared a sort of middle road,” Katharine Hepburn told Barbara Walters in a 1981 interview. One hundred and nine years after the screen icon was born in Hartford, Connecticut, it’s remarkable how much that decision to wear pants continues to set her apart—not just from her Old Hollywood peers, but from modern stars who still aren’t nearly as daring.

At the age of nine, Hepburn had her head shaved, then ran and put on her older brother’s clothes. “I had a phase as a child when I wished I was a boy because I thought boys had all the fun,” she told biographer Charlotte Chandler, in I Know Where I’m Going: Katharine Hepburn: A Personal Biography. “I did wish I could be a boy, so I decided I wanted people to call me Jimmy. I just liked the name Jimmy. I told my family I wanted to be called Jimmy.” An actress in the making, Hepburn’s cross-dressing alter ego was a part she played. “I created Jimmy for the others,” she emphasized to Chandler. “Inside I never felt like Jimmy.”

When Hepburn hit the silver screen in 1932, shortly after graduating from Bryn Mawr, Hollywood already wasn’t quite sure what to make of her. George Cukor, who directed Hepburn’s first screen performance in A Bill of Divorcement, in 1932, and who went on to be a lifelong friend, said, “The audience had never seen a girl like that—she seemed to bark at them. She didn’t play for sympathy at all. At first, the audience wasn’t quite sure whether it liked her or not.”

Sometimes described as “too masculine” or “too rough,” Hepburn could be difficult to cast opposite the leading men of the day. George Stevens, who directed Hepburn in Alice Adams (1935), had to teach her how to do love scenes, because, he told biographer Charles Higham, “she had always thought that to play a love scene with a man involved standing up straight and talking to him strong, eye to eye.” For Christopher Strong (1933) even lesbian director Dorothy Arzner implored Hepburn to make herself appear more feminine: “Kate wasn’t someone you could mold easily, that you could control,” Arzner told Hepburn biographer Charles Higham in Kate: The Life of Katharine Hepburn. “She was extremely strong-willed. Her tone was all wrong; I had to soften her constantly.”

From Collection Christiophel/Alamy.

While her inexhaustible, aggressive energy defined her screen presence, her fashion, which no doubt was an expression of her androgynous sensibility, raised more than a few eyebrows. In the early 1930s, women’s fashion had not yet been liberated by the practicalities of World War II, when women en masse took positions in businesses and industries while the men were at war. Women could be, and were, arrested if they wore pants in public, detained for “masquerading as men.” It was the decade that saw the publication of Freud’s theories of femininity, female masculinity, and female perversion, whereby the desire to don pants for Freud was conveniently reduced (like most things for women) to penis envy—and a sure sign of lesbianism. Clothing, rather, was still perceived as a manifestation of one’s gender, and “mannish” trousers were feared to reflect a perversity within women. Enter Katharine Hepburn. In 1933 Movie Classic magazine ran the feature “Will It Be Trousers For Women?,” and Hepburn was listed along with Greta Garbo, Marlene Dietrich, Mozelle Britton, and Fay Wray as “among the stars who have lined up on the side of trousers for women.”