Occupational segregation by sex remains the most pervasive aspect of the labour market. In the past, most research on this topic has concentrated on explanations of women’s segregation into low paid and low status occupations, or investigations of women who have crossed gender boundaries into men’s jobs, and the potential impact on them and the occupations. In contrast, this article reports on a small-scale, qualitative study of ten men who have crossed into what are generally defined as ‘women’s jobs’. In doing so, one of the impacts on them has been that they have experienced challenges to their masculine identity from various sources and in a variety of ways. The men’s reactions to these challenges, and their strategies for developing and accommodating their masculinity in light of these challenges, are illuminating. They either attempted to maintain a traditional masculinity by distancing themselves from female colleagues, and/or partially (re)constructed a different masculinity by identifying with their non-traditional occupations. This they did as often as they deemed necessary as a response to different forms of challenge to their gender identities from both men and women. Finally, the article argues that these responses work to maintain the men as the dominant gender, even in these traditionally defined ‘women’s jobs’.