Katharine Hepburn dressed as a boy in the movie Sylvia Scarlett. (AFP/Getty Images)
There has been a lot of speculation regarding Katharine Hepburn's orientation and gender experience, and though she was rumored to have affairs with some women, if she was queer, she was not out. There is a biography that says she had a boy alter-ego named Jimmy when she was a kid and that she had several affairs with women, and that she and Spencer Tracy were basically beards for each other. But there is a lot of refutation of the things said in that biography and I can't put my hands on the source material.
Anyway, here she is being adorable and letting some girl put an eyeliner mustache on her.