This thesis is intended to contribute to anthropological and sociological debates on the sources of gender identity and the strategies that are entailed in its management. Cross-dressing among men in western societies has been studied from two major perspectives. One comes from behavioural psychologists and psychiatrists who regard transvestism as deviant behaviour that requires counselling and treatment. This medical model has limited use and is not acceptable to transvestites. Cross-dressing has also been studied from a social scientific perspective that views transvestism in relation to the performance of gender. It is within this perspective that the results of my research are primarily located. The example of male transvestism is particularly instructive because it demonstrates a creative play within shifting sexual boundaries. Male transvestites challenge assumptions about gender practices in the context of every day life when expressing their 'dedoublement' that juxtapose masculinity and femininity. Transvestism is thus an attack on the very notion of gender deviance, which is being mounted by small groups of otherwise very 'ordinary' men. These men also have a developed masculine image reflecting a specifically regional discourse of masculinity that has its origin in socio-economic backgrounds based on heavy industry and its collapse in the 1960s. A similar masculine ideology is present in both areas of my research: the North East of England and Liege in Belgium. Transvestites, by asserting 'feminine within the masculine', seriously transgress this ideology. Transvestites are often rejected on the basis of their non-normative behaviour. The boundaries between 'normal' and 'deviant' are reinforced on a daily basis through, among others factors, the media. To avoid being labelled 'deviant', transvestites tend to keep their behaviour secret or meet with others in groups that have recently began to flourish.