Background: As school dropout is an important public health problem that needs to be addressed, we set out to examine whether and how, beyond the well-known effects of sex, gender beliefs and self-reported masculinity and femininity are related to school dropout. Methods: The study used a case-control design, consisting of 330 dropout cases and 330 controls still attending school. The respondents, aged between 18 and 23 years, living in the south-east of the Netherlands, were sent a self-administered questionnaire. Separate logistic regression analyses for the male and female participants were used to explore the relation between dropout and gender, controlling for sociodemographic determinants. Results: As indicated by significant curvilinearity, young women were less likely to drop out when they occupied an intermediate positions on the gender variables. Odds of dropout were elevated among highly masculine women (odds ratio = 2.1, 95% confidence interval: 1.1–4.1), and, as indicated by significant interactions, also among highly masculine men with strong normative masculine beliefs and in feminine men who simultaneously considered themselves low on masculinity. Conclusions: Beyond sex, gender is important in the explanation of school dropout. To prevent dropout, public health professionals should assess, monitor and intervene on the basis of gender characteristics.