This conference paper examines ways in which visual art makes transgender issues of health and wellbeing visible to transgender people and the wider social sphere. Transgender identities are as divergent as transgender experiences, but they are also often constructed and negotiated through and in opposition to medical and legislative discourse and practice. For these groups identity formation is complex, often problematic within existing classificatory systems, and limited linguistic possibilities that rest upon a male/female gender binary not always able to account for different practices and experiences of gender and sexual diversity. The paper analyses the impact of medical, psychiatric, legal frameworks on transgendered identities, and the constraints they impose. It explores the contribution made by art and cinema in providing non-traditional images and ideas that help transgendered people to form and articulate their identity to themselves and to the non-transgendered public. It examines the ways in which art and cinema articulate identities transgressive of the binary framework of male and female, to give representation and expressive reality to the multiple perspectives of transgendered lived experience.