We investigate how the stratification of the school system influences gender-specific occupational expectations of adolescents: via school-specific gender-typical aspirations or expectations related to social status. We analyze cross-sectional data from the National Education Panel Study (NEPS, waves 2010–2011) Starting Cohort 4 on ninth graders in Germany. Using multi-level mediation analyses, we show that school-specific occupational aspirations mediate the influence of the school type on adolescents’ occupational expectations. Low-level school types, especially lower secondary schools (Hauptschule), are characterized by more gender-specific occupational aspirations than upper secondary schools (Gymnasium). In addition, school-typical occupational expectations with regard to social status are also important for explaining differences in gender-typical occupational expectations. This might be explained by the highly gender segregated opportunity structure, especially in the low-skilled labor market segment.