This paper provides a view of the experiences of former high school apprentices in Canada. Conceptually, we draw on the work of Bourdieu with particular attention to vocational habitus, as well as feminist writers who discuss the gendered construction of skill and gender relations in the workplace and family. Empirically, we present our analysis of survey data from 173 male and female apprentices in two provinces and interviews with female apprentices in Alberta. Our data provide insights into youths' school experiences as well as their subsequent trajectories and plans for the future. Findings suggest that female youth relied more than young men on the support of families and external influences in choosing a trade. Young women in female-dominated trades faced different but no less significant challenges than those in male-dominated trades. Women who succeeded in completing apprenticeship training did so because of their family habitus and expansive training experiences.