It reminds me of a kdrama that reaaly liked. Title is To the beautiful you. Girl liked guy. Guy goes to an all boys school. Girl enrolls to the school as a guy. There was a pageant where the girl that was in disguise as a guy had to dress up as a girl.
Because someone should... it literally has a female, dressing up as a male, who then is asked to pretend to be a female. PRICELESS.