8 Historical Crossdressers: Women in a Man’s World is an article by Miss Cellania featured in Mental Floss where she introduces eight famous women who crossdressed in history. Here are # 4 and #7:
#4 Frances Clayton :
There are quite a few stories of women serving in the Civil War disguised as men. Estimates range from 150 to 400 such soldiers! Many distinguished themselves, and were even honored for their service after the war. One such hero was Frances L. Clayton, who wore men’s clothing to enlist in the Union Army with her husband. She was wounded three times in battle, and was even taken prisoner by the Confederacy. After her husband was killed, she confided her sex to her commanding officer and was granted an honorable discharge.
#7 Billy Tipton:
Billy Tipton was a jazz musician who played piano and saxophone. Born in 1914 as Dorothy Lucille Tipton, she was denied a spot in her high school band because she was a girl. Billy was already a professional musician when she began dressing as a man to better blend in with the other musicians, and by 1940 presented herself as a man both publicly and privately. While playing with various bands, she had long-term relationships with several women who never knew her true sex. Although Billy never legally married, she adopted three sons with stripper Kitty Oakes. Neither Oakes nor their sons knew Tipton’s sex until her death in 1989, at age 74.