Two silent films in which cross-dressing plays a major role are:
 
_Poor Little Rich Girl_ starring Mary Pickford (Maurice Tourneur, 1917)
_Florida Enchantment_ c.1913 - I'm not sure of the director, but the film is
available on the "Origin of the Fantasy Feature" video from the Library of
Congress
 
In the Pickford film, the cross-dressing is girl to boy; in _Florida
Enchantment_ two women (one white, one black) dress as men. The latter is
very interesting in terms of performances of race as well as gender.
 
Although not often the primary focus of the films, moments of cross-dressing
were pivotal in several of Alice Guy-Blache's Solax films. In fact, I think
it was fairly common in films of her era (as others have mentioned,
cross-dressing was a convention of theatre and vaudeville, so it's not
surprising that it would show up in early films as well).
 
- Amelie Hastie
University of Wisconsin-Milwaukee
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