Charlie Chaplin: A woman (1915)

A Woman was Charlie Chaplin's ninth film for Essanay Films. It was made in Los Angeles at the Majestic Studio and released in 1915. Chaplin's character is dressed as a woman when he meets in a part Edna (Edna Purviance) and her mother (Marta Golden) and father {Charles Insley}. It is the third and final time that Chaplin played the role of a woman on film. He played a woman in two Keystone films: The Masquerader and A Busy Day.
https://en.wikipedia.org/wiki/A_Woman