For decades, scholarship on the Great War (World War I) noted moments of crossdressing as mere entertainment, one of the strange absurdities that the war produced without any consideration of the gendered and sexual components of such displays. More recently, scholars have focused on the homoerotics of men performing for other men. In contrast, this article suggests that female impersonation during the Great War allowed for the existence of pleasures resistant to categorization. It argues that female impersonation allowed for a rich cultural lexicon based on ambiguity. By using postcards, letters, and descriptions published during the war and shortly after, the author shows that female impersonation allowed men -as both impersonators and audienceto experience a pleasurable dissociation in an environment defined by passivity and alienation.