The paper reports on the Greek bifurcated post-16 educational landscape, drawing upon an ethnographic study that examined young people’s biographies as entwined with the multifaceted workings of identity formation. It explores the social conditionings of educational decision-making processes in regards to young people’s transitions to post-compulsory academic and vocational institutions with distinct scholastic status and social value. Educational ‘choice’ is conceptualised as a dynamic manifestation of a corpus of dispositions, attitudes and aspirations, conditioned by unequal access to economic, cultural and social capitals, (re)-shaped in the course of personal and familial histories and (re)-structured in the light of institutional arrangements and habituses (Bourdieu, 2001; Reay et al, 2001; McDonough, 1997; Colley, 2003). Young people’s narratives are analysed with particular emphasis on experience and meaning in an attempt to locate the subtle facets of their educational decision-making. In exploring the narrative textures of 12 young people’s accounts, asymmetrical patterns of vocational ‘choices’ are identified as situated social practices central to the process of becoming and produced in the balancing acts between constraints and opportunities, manifold resources as well as dominant discourses and imagined futures. The pathways are institutionally-mediated but also resisted by young people who agentically engage in vocational choice-making.