SIDESHOW X-DRESSERS
Strictly speaking, cross-dressing is the act of wearing the clothing of another gender for any reason.  In American show business female impersonation dates back at least to the 1840's. So one should expect to find cross-dressers in the world of the Ten-in-One since this was, after all, a distinct branch of popular entertainment. Sometimes men would dress as women in the sideshow because a female ____ (fill in the blank) was always a bigger draw. Sometimes there were gender identity issues which I'm sure was the case with some "bearded ladies".  And sometimes ......   well, you look at the pictures and see what YOU think.
Julian Eltinge is credited with bringing female impersonation to its peak in America in the early 1900's
Perhaps fat man John Robinson thought he  would be more successful  as a fat lady
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Showman G.A. Farini adopted Sam Wasgate who became "El Niņo" who became "Lulu" (on the left) in the 1870's. Read "The Great Farini" by Shane Peacock for more
Two photos of Sam as "El Niņo Farini". For more on the life of William Hunt aka Guillermo Farini read "The Great Farini" by Shane Peacock