A constant theme in the history of gay men’s dress has been the hyperbolic performance and radical confusion of masculine and feminine gender codes. This research seeks to understand how gender conventions influence the stylistic motivations and dress practices of contemporary gay men. Guided by the theory of gender performativity, this article presents the sartorial biographies of three urban-residing young gay men in Toronto, Canada, who each come from different ethnic backgrounds. Eschewing gender binaries, these men combine unique variations of conventionally masculine and feminine clothing to formulate distinctive looks. Influenced by their sexuality and intersectional identities, these men blend gendered dress codes to express their individuality as well as stimulate meaningful dialogue about gender. The experiences of the men in this study can be seen as representating the influence of neoliberal political ideology and the current postpostmodern cultural climate.