Stunning Black and White Portraits of Katharine Hepburn Dressed as a Boy in “Sylvia Scarlett” (1935)

Katharine Hepburn famously dressed as a boy in Sylvia Scarlett (1935), directed by George Cukor. In the film, she plays Sylvia Scarlett, a young woman who disguises herself as a boy named “Sylvester” to help her father escape from France to England after a financial scandal.

Hepburn’s character challenges gender norms of the time, and her portrayal was daring and ahead of its era. Her short hair, masculine attire, and convincing boyish mannerisms contributed to the film's unique tone.

The film is now considered a cult classic, especially among LGBTQ+ audiences, for its exploration of gender identity and ambiguous sexual tensions. There are scenes where both male and female characters are attracted to “Sylvester,” adding a layer of complexity to the narrative.

Despite Hepburn’s bold performance, Sylvia Scarlett was a box office flop at the time. However, it has since gained recognition for its daring themes and Hepburn's risk-taking.