The paper discusses factors impacting on boys' educational aspirations at two case-study schools in urban Jamaica. It focuses on boys' experience of their educational environment in relation to social, cultural and economic factors, which shapes the nature of their aspirations towards higher education. The study utilised Bourdieu's notion of "capital" grounded in a critical realist meta-theoretical framework, the narratives of the participants and the researcher's experiential understanding as a participant observer to explore boys' aspirations over a 12-month period. The findings from the study suggested that boys' educational aspirations are complex and affected by their level of capital in relation to persistent narratives from family and the Jamaican Diaspora within high-income countries like the UK, the USA and Canada.