One of the clearest manifestations of how gender norms come into play, is the overrepresentation of men and women in gender stereotypical occupations. Therefore, this paper studies occupational preferences and their relationship with perceived gender typicality, perceived pressure for gender conformity from friends and discontent with gender boundaries among preadolescents (N = 795) in the Dutch-speaking part of Belgium (Flanders). Discriminant analysis enables us to develop an original and sensitive measure for gendered preferences. Subsequently, we use multivariate regression analyses to study the variation in gendered occupational preferences. Models are separately estimated for boys (n = 395) and girls (n = 400) and further include their academic self-concept, socio-economic and socio-cultural background. The main finding of this study indicates that boys’ and girls’ stereotypical occupational preferences are differently related to gender norms. While boys’ gender stereotypical preferences relate to their perceived pressure for gender conformity from friends, this does not apply to girls. For girls, the results indicate that their stereotypical occupational preferences reflect an important part of their gender typical identity. Moreover, girls who feel confident about their academic capabilities aspire less gender stereotypical occupations. The results also indicate the relevance of considering socio-economic and socio-cultural background variables when studying preadolescents’ occupational preferences.