Ethnic and social inequalities in education are persistent in Flanders (Belgium) and the Netherlands, and these inequalities can be strengthened or weakened through particular features of educational systems. In this chapter, we focus on one particular aspect that shapes the educational routes of young people to acquire an educational qualification, namely switching practices. We aim to shed light on and compare the switching practices between fields of study/tracks during one’s educational trajectory, in and outside mainstream vocational secondary education. Our findings indicate that in both systems, youngsters had distinct institutionalized opportunities to change track/field of study during their educational career. In the Dutch educational system, youngsters are more institutionally supported when changing from more vocational to more academic tracks or fields of study. In Flanders, youngsters could more easily change between fields of study within the vocational track during the academic year, which could help them to more efficiently discover a field of study that matches their interests and abilities, but also lead to more confusion, random changes and a lack of direction. In both systems, policy makers should pay more attention to the guidance of students when making choices, across educational programmes, institutions and schools.