Understanding social disparities in educational attainment requires understanding of students' decision-making throughout their educational career. We focused on students' pathways throughout upper secondary and higher education (HE), identified common types of pathways and studied the role of SES as a determinant of students' pathways. Additionally, we researched the role of engagement for overcoming socioeconomic disadvantages in students' educational decision-making. Using data from 965 Flemish students, optimal matching analyses identified seven distinct pathways throughout upper secondary and HE. While pathways largely mirrored the tracked structure of the Flemish educational system, there was considerable within-track heterogeneity. Multinomial regression analyses demonstrated that even among the academic track students, socioeconomic background affected programme choice and long-term academic success. Less engaged students were less likely to follow university pathways. Moreover, higher cognitive engagement decreased disadvantaged students' chances of ending up in typical vocational pathways.