Cross Dressing Movies

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

After becoming a licensed engineer abroad, Lucyna comes back to Poland and looks for a job. Because her wealthy father thinks it's inappropriate for...

Charley Wyckham and Jack Chesney pressure fellow student Fancourt Babberly to pose as Charley's Brazilian Aunt Donna Lucia. Their purpose is to have...

Shakespeare's comedy of gender confusion, in which a girl disguises herself as a man to be near the count she adores, only to be pursued by the woman...

Chaos ensues when two brothers, Dhananjay and Shantanu, force two friends to pose as their wives as their landlady allows only married couples as...

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 hot young hustler finds himself in uncharted waters when he spends the night with a client who's far from the "johns" he's used to servicing.

A poet, who works as a waiter to make ends meet, postures as a female singer to end a blood feud between two families.

"Lucky" Davis, a ladies-man and a devil-may-care U. S. Marine Sergeant, is leading a Marine-squadron on an expedition through a Phillipine jungle...

Baroness Marika von Korossy dresses up as a man, in order to compete in a horse race. Her victorious horse, Satan, will only allow her to ride him...

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

Old Mother Riley loses her laundry job and then battles her ex-boss in a parliamentary election.

A young woman who disguises herself as a man to go gold prospecting after her father and brother forbid her from joining them.

A lady manager of newly formed record house places his administrator, disguised as a cleaning lady, in competing record house. She needs to get the...

In Prohibition-era Chicago, musicians Joe and Jerry witness a mob hit, and flee the state in an all-female band disguised as Josephine and Daphne,...

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...

The stooges are singing comedic waiters, enlisted by two doctors to try and cheer up a depressed little girl, whose banker-father has gone missing...

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

Two guys found a treasure map. They decided to make a plan to approach and figure out the truth behind it. One had to disguise as a woman and other...

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