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.
She’s the Man (2006)
The Look: A short haircut, baggy sportswear, and, well, not much else are what Bynes employs to secure herself a place on the boy’s soccer team.
Did She Pass? Bynes’s chipmunk vocals did little to convince us of her boyhood, especially next to Channing Tatum.
Albert Nobbs (2011)
The Look: The film highlights the actress’s handsome bone structure and hides her slim frame with dowdy manservant garb.
Did She Pass? The 19th-century thought so, but Close’s frailness and strange asexuality raised a few eyebrows.
Just One of the Guys (1985)
The Look: A varsity jacket and slick black curls helped Terry break into the high school newspaper.
Did She Pass? Absolutely not. Aside from her angelic face, Hyser’s figure created odd shapes beneath her button-downs.
The Look: Babs used a pageboy coif and Orthodox vestments as a woman trying to “get her learn on” in a man’s world.
Did She Pass? Nope, but Streisand’s grand persona often overshadows the roles she plays, despite gender.
The Look: Once made into “Count Victor Grazinski,” Andrews had a Euro-chic look that was debonair enough to play onscreen.
Did She Pass? Well, Andrews showed that a man could fall for a man playing a female impersonator—played by a woman. So that seems like a pretty clear win.
I’m Not There (2007)
The Look: Wayfarers, ratty hair, and a constant cigarette were mere accessories to this jittery copy.
Did She Pass? She? Blanchett must’ve hired an exorcist to recover from her perfect channeling of the ’60s-era legend.