Internationally, boys from working-class backgrounds are often the most likely to disengage from their formal education. Research on the educational experience of working-class boys has focused heavily on their identity barriers, often positioning these young men as either vulnerable or volatile in their formal education. Social theorists have sought to address the historical and cultural embedded (gendered) practices which influence the identity work of working-class boys. This conceptual article contributes to the study of working-class boyhood and education through first synthesizing key themes present in the historic and contemporary literature before adopting a feminist post-structural stance to consider how these themes are informed by our understandings of the discursive production of masculinities. Then, in the second half of the paper, we make visible what has been at the margins in the scholarship -- identity versatility -- which we define as contextual and agentic adaptation. Attention to versatility, we feel, offers the potential for a nuanced analysis regarding working-class boyhood, learner identities and educational engagement.