The Most Daring Thing About Katharine Hepburn? Her Pants

“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.”

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