Charlie Chaplin played a woman in 3 of his films. This was a common thing with comedians in early cinema.
A Busy Day - Keystone 1914 (Here he played an actual woman)
The Masquerader - Keystone 1914 He plays an actor who gets fired, comes and fools all of the men. I think he looked the prettiest in this film with kiss curl & beauty mark.
A Woman - Essanay 1915 - His sweethearts father (who is a big flirt) hates him, he dresses as a woman and has him and his friend coming on to him. Charlie gets found out and tossed.