How He Is She?

Orlando (1992)

The Look: An androgynous ginger dressed in big flouncy boy blouses to portray an Elizabethan Age nobleman.

Did She Pass? As the eponymous Orlando, Swinton changes sex midway through the film, but for many years she was considered a luminous gender-bender in her everyday life. She's currently saying she will play Auntie Mame in a remake of the classic.