“The Clothes Make the Man: Theatrical Crossdressing as Expression of Gender Fluidity in Seventeenth- through Nineteenth-Century Performance” explores theatrical crossdressing, specifically masculinity embodied by a female actor, in British and American performances starting in 1689 and ending in 1914. By examining specific performances, plays and historical individuals over the course of 225 years, this dissertation traces theorizations of gender during these different time periods, combining a close reading of texts with historical research and historiography to offer transgender readings of characters, performers and historical individuals. This project challenges the gender normative assumptions in the theatre scholarship, that previously read these masculine performances through a narrow lens, without fully considering gender identity. The wide temporal range examined in this dissertation allows for the development of a genealogy of genderfluid and transgender performance.