In the course of educational expansion, gender differences in access to higher education have decreased substantially in many European countries. In Germany women are currently over-represented in upper secondary education and more frequently attain a general qualification for university entrance. Despite those advantages, women still enrol in higher education less frequently. Even where they apply to higher education, their field of study choices differ from those of men. Drawing on recent data on upper secondary graduates, we seek to understand which factors account for both phenomena. Our findings suggest that the growing gender gap in the transition to higher education can be largely ascribed to differential perceptions of labour market outcomes. In addition, the more risk-averse assessment of study costs and success probabilities are more important for women's decision not to enter higher education. Furthermore, the gender gap in the choice of a technical field can be explained by differences in the subjectively perceived comparative advantage in technical skills and by differences in educational motivations and conceptions of life and career plans. These results lead to the conclusion that gendered educational choices are the consequence of effects that have their provenance much earlier in life. (Contains 7 notes, 2 figures, and 3 tables.)