This study set out to conduct a comparative analysis of self-identifying gender non-conforming youth residing on the urban peripheries of Cape Town, against the realities of gender non-conforming youth in more affluent, resourced communities in the southern suburbs of Cape Town, South Africa. The intention of this study was to explore the dynamics that make for different possibilities to express gender non-conformity amongst youth, as well as the opportunities available for these young people to recreate their identities in ways that make sense to themselves, and allow for a more fulfilling sense of self in contemporary South Africa.