Young women would often disguise themselves as a man in Western movies so they could go ride the range instead of having to stay home in the Scrubbery. Hats were a big help in the old days of course........
Ellie May always wanted to be equal to a man but she didn't feel the need to pretend.
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Barbara Windsor in Carry on Dick
Steve
Judy Loe as Chief Petty Officer Russell in Ripping Yarns: The Curse of the Claw
Samntha Eggar in the 1962 film Dr. Crippen, playing the real life role of Ethel Le Neve who masqueraded as a certain Master Robinson aboard the SS Montrose.
Joan Marshall was very convincing as a man in Homicidal - so much so, I actually thought that was a real guy who portrayed the Warren character. She used the name Jean Arless for that role. It is available on DVD and worth watching