Much educational research on working-class boys has focused on their failure and lack of aspiration. However, there has been little research on working-class boys’ experiences of success. The very idea of being educationally successful and working class is problematic, as success has been argued to be dependent on the abandonment of aspects of working-class background. This article highlights the difficulties that some working-class grammar school boys face in reconciling their identity with educational success. For these boys the issue of identity is complex and there is a conflict between their identity, based on their class background, and their identity as an aspiring student. Using Bourdieu’s theory of habitus, this article explores the complexities associated with identities that are developing in social fields different from those in which they originated, and discusses how this impacts emotionally on working-class boys.