The 2008 Review of Australian Higher Education recommended ‘raising aspirations’ as a key strategy for widening participation in university, especially for historically underrepresented groups including Indigenous people, those from lower socio-economic status backgrounds and those from rural and remote locations. The premise here is that under-enrolment has been (at least in part) a function of diminished aspiration for higher education. While several studies have since challenged this view, vast inequities remain in terms of which students are most likely to end up at university and in the most prestigious programs. In this paper, we draw on survey and focus group data collected as part of a study investigating the aspirations of students (n = 6,492, aged 8-18 years) enrolled in government schools in New South Wales, Australia, to provide a more nuanced analysis of the relationship between ‘choice making’ and ‘aspiration’. Drawing on Ball, Reay and David’s (2002) heuristic of ‘embedded and contingent choosers’, we examine different discourses of choice and the complexities of ‘choosing’ that play out within aspiration formation. First, we use survey data to compare intention to enrol in university and the kinds of occupations students aspire to in the future. Next, we narrow the focus to two case studies exploring the cultural and structural contexts of students’ lives: Harbour View High School, a metropolitan secondary school situated in a relatively advantaged area (n = 43 participants); and, Mountainside Central School, a regional central school situated in a relatively disadvantaged area (n = 43 participants). We found that the vast majority of students at Harbour View High School could be characterised as embedded choosers; that is, university was spoken about with confidence and certainty, often stemming from an intergenerational history of higher education and, in many cases, conversation focused on which university to attend, including international options. In comparison, most students at Mountainside Central School were contingent choosers: the idea of university was distant, most students had no family history of higher education, and choices were constrained by finance and location. We argue that choice-making plays out differently among students, with contingent choosers facing challenges that make the decision to pursue higher education more precarious – even if they aspire to this pathway. Therefore, efforts to increase access to university for a diverse group of students must move beyond a focus on aspiration, and consider how cultural and structural contexts impinge on choice, and ultimately, decision-making.