This study addresses the complex issues of etiology and conceptualization of gender variance in the modern West. By analyzing medical, psychological, and popular approaches to gender variance, I demonstrate the highly political nature of each of these paradigms and how gender variant individuals engage with these discourses in the elaboration of their own gender identities. I focus on the role of institutional authority in shaping popular ideas about gender variance and the relationship of gender variant individuals who seek medical intervention towards the systems that regulate their care. Also relevant are the tensions between those who view gender variance as an expression of an essential cross-sex gender (as in traditional transsexual narrative) and those who believe that gender is socially constructed and non-binary. I finally argue that the standards of treatment for gender variant individuals pertains more to the medical legitimization of their identities than with necessarily improving outcomes.