This paper draws on a Linguistic Ethnography (Blommaert & Rampton 2011) of a group of academically elite students in Singapore. The group comprises locals born in Singapore, as well as immigrants from China and Vietnam. They all attended a top-ranked secondary school in Singapore. The paper presents data from interviews and a focus group discussion with them about their aspirations and educational pathways. These academically elite students describe a conventional aspiration amongst their peers involving transnational mobility and attending top-ranked universities in the US and UK. They discursively construct this aspiration as preferred, with a sense that they are expected to conform to such a trajectory. It is argued that their consistent orientation toward the ideal trajectory and production of discourse about it denotes a collective moral stance (Ochs & Capps 2002), and hence a disposition embedded in a social field (Hanks 2005). In response to Archer’s (2012) theorisations that dominant modes of reflexivity have changed, the students’ relatively stable orientations and ways of acting demonstrate how Bourdieu’s notion of habitus continues to be relevant in late-modernity. In practical terms, this study also shows a clear link between elite schools, and the aspirations and resultant trajectories of individuals. This has direct implications for policy-makers in Singapore where the Ministry of Education has been attempting to curb elitism in the education system.