Crossdressing before 1959?  The first title that comes to mind is Sylvia
Scarlett (1935), in which Hepburn dresses as a boy for much of the film.
There were also something like half-a-dozen versions of "Charley's Aunt"
filmed by the 1940s.  So there's a start.
 
JRG
 
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John R. Groch <[log in to unmask]>            |  "Work!  FINISH!  THEN sleep."
English Department/Film Studies Program    |     -- The Monster,
Univ. of Pittsburgh, Pittsburgh, PA 15260  |        "Bride of Frankenstein"
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