In this article our focus is on the persistent gendered divisions in educational routes of young people who choose a vocational path after compulsory education in Finland. We analyse how gendered subjectivities are constructed within the practices of educational and vocational guidance and within student cultures in the comprehensive school, as well as the way in which young people process understandings of themselves and their expectations during and after vocational education. In addition, we explore young people's ways to negotiate with disciplinary practices of the educational system. The paper draws on three ethnographic studies, and on feminist post-structural and materialist theories, intertwined with contextualised ethnographic perspectives. Our analysis reveals some patterns that might work as obstacles in the process towards reducing gender segregation in education and the labour market. We suggest that whilst gendered choices are sometimes taken for granted, gender dichotomy is often emphasised even if young people choose "differently". (Contains 4 notes.)