Cross Dressing Movies

A cross-dressing Adolf Hitler sings tasteless, but humorous musical numbers.

Lillian dresses as a man to gain access to a boy's school. (from Performing Queer Female Identity on Screen: A Critical Analysis of Five Recent Films)

A girl posing as a knight's male valet is vamped by his fiancée

A student is pressured into pretending to be a classmate's Aunt so he can act as a false chaperone.

To conquer his beautiful mother without insospettirne, Polidor dresses for women and can thus safely visit the house, but was immediately made...

Muggs' rich Uncle Pete is coming to visit. Unfortunately, Muggs' late father had bragged that he had seven kids, so Muggs recruits the members of the...

Based on the stage musical of the same name, this is the tale of a princess who grew up loving fairy tales and finds herself thrust into one where...

A young woman poses as a boy to ingratiate herself better with her strict aristocratic grandfather and to get him to better accept the new freer ways...

A Robust Romeo is a 1914 movie starring Roscoe Arbuckle and Emma Bell Clifton.

Low budget softcore farce where two men cross-dress to go into a women's prison.

A company of soldiers is visiting a small village. The mayor (?) locks away his daughter because she is very adventurous...

This film evolves around a mother and a son and their day on May 17, 2013. The story starts in the morning when a woman discovers her son wearing her...

Superman's pal Jimmy Olsen gets his own story. Boy meets girl. Boy loses girl. Boy meets boy!

A very old lady has lost her way in a city and a distinguished gentleman decides to follow her home.

Marta has found a dress that is not hers in her boyfriend Fer's room, all the trust she has placed in him over years of relationship is shaken.

Robinet disguises himself as a woman to get away from his girlfriend’s husband, and discovers the unexpected pleasures of public drag amidst...

Parental fears reach an early boil when five-year-old Saúl announces that he wants to dress up as a little Siren for the school's fancy dress...

A young woman must pretend to be a man to visit her grandfather, and gets into some romantic scrapes in the process.

Billy and His Pal, released on February 16, 1911, is about a cowboy, Jim (Francis Ford), who is idolised by young Billy (actress Edith Storey in...