There are a whole host of movies where female characters wear masculine garb, for a variety of reasons. Sometimes they are hiding their true identity, and sometimes they’re just wearing the pants, so to speak! Here are a few classic ones (and a few lesser known), starting with probably the most famous ever woman-in-a-tux….
Amy Jolly (Marlene Dietrich) in Morocco
Princess Mary Tudor (Glynis Johns) in The Sword and the Rose
Velvet (Elizabeth Taylor) in National Velvet
Annie Hall (Diane Keaton) in Annie Hall
George Sand (Judy Davis) in Impromptu
Natty Gann (Meredith Salenger) in The Journey of Natty Gann
Bob (Gabrielle Glaister) in Blackadder
Snow White (Lily Collins) in Mirror Mirror
(okay, these aren’t really boys’ clothes per se… I mean, that is a corset after all… but it was a change into more masculine, swordsman-style garb after her pouffy dress!)
Snow White (Kristen Stewart) in Snow White and the Huntsman
(as with Mirror Mirror, Snow White’s attire is not technically “boys’ clothes”, but tunic + leggings is certainly on the masculine side compared to a dress – at least for the era they were presumably trying to evoke)
Valerian (Caitlin Clarke) in Dragonslayer
Eowyn (Miranda Otto) in Lord of the Rings
…and the best “reveal” ever….
P.S. Thank you to a commenter (below), for suggesting Lou McCloud from The Young Riders. I’ve never watched it myself, but here’s a great pic: