This chapter focuses on teenage boys’ embodied learner identities and educational aspirations, contributing to an understanding of working-class masculinities as complex rather than monolithic constructs. The chapter reveals diversity and complexity in boys’ embodied performances of masculinity even when they operate within a hegemonic framework. The research draws on an ethnographic study of working-class teenage boys in a secondary school in Belfast, Northern Ireland, and presents the narratives of two individuals who, through their practices and dispositions, display complexities and apparent contradictions in the embodiment of classed and gendered identities within a school environment that demands both machismo and a pro-learning attitude. Through an exploration of the data, the intention is to complicate some of the constructions of hegemonic masculinity as necessarily anti-school, lacking aspiration, homophobic, and misogynistic.