Today’s trans feature silent:
A Florida Enchantment (1914)

Not to be confused with cross-dressing farces, which were plentiful in the early days of cinema, films with actual transgender themes are much rarer than those dealing with gay or lesbian issues. Sidney Drew’s 1914 satirical comedy A Florida Enchantment is probably the foremost example from the silent era.

Staring Edith Storey (Twelfth Night, The Christian), Ethel Lloyd, and the film’s director, Sidney Drew, A Florida Enchantment tells the story of a neglected woman’s discovery of a casket containing a hundred year old secret: a way for a woman to become a man and vice versa.

Though primarily a comedy, the film is rife with social commentary on gender roles and their breaking, particularly in the last two reels when the “vice versa” aspect of the secret is put to use.