The authors explore the ways in which the Internet functions to communicate about cross-dressing as part of a larger cultural discourse surrounding gender. As a widely used tool to dialogue on the topic of appearance, the Internet also helps to establish and even alter gendered identities. The seamless realm of the Internet allows such identities to cross cultural boundaries instantly and without regard for real physical space. Based on 30 Websites of cross-dressers collected and analyzed, this essay examines the ways that individuals use this virtual world for purposes of cross-dressing. As a study of human behavior and dress, this research has important implications for furthering our understanding of how cyberspace operates as a newly established socio-cultural realm and participates in the current scholarly discourse on the topic of the Internet as a new vehicle for the study of dress and identity.