The term transvestism is mistakenly applied to describe all categories of cross-dressing. This leads to theoretical and clinical confusion, as men who cross dress share some common features but differ greatly in regards to their aims and intentions. The aim of this paper is to provide an understanding of the formation and development of transvestism that extends beyond the classical psychoanalytic explanation of castration anxiety. Today, more emphasis is placed on anxieties emanating from the early symbiotic relationship with the mother, the formation of the sense of self and unresolved separation anxiety. Insights gained from clinical work with transvestites can enhance our understanding of the construction of masculinity and the male's greater gender conflicts and sexual insecurities. Also, the study of the homosexual fantasies or intense homophobia experienced by some fetishistic cross-dressers relate more to gender issues and conflicts than sexual orientation.