Inspired by scholarly calls to focus more intently on the influence of context on leaders' construction and negotiation of identity, this paper draws on evidence from our Economic and Social Research Council (ESRC) project in London, New York City and Toronto. Throughout the paper, we strive to illuminate how the city-based context influences how race/ethnicity is experienced and described. We use social identity theory, organisational fit and in-group prototypes to frame school leaders' explicit discuss race/ethnicity when reflecting on identity. We describe our data gathering process using our Professional Identity card-sort Tool, which guided leaders' reflections on identity. The analysis details how we extracted and interpreted evidence from leaders who were explicit about the interrelationship between their own personal racial/ethnic identification and its alignment or misalignment with their school-level communities. We explore how different city contexts influence leader experience of in-groups and out-groups and the related leadership challenges and opportunities. In conclusion, we reflect on the influence that structures, policies and communities have on how leaders experience identity and the possible implications for their work. We also explore the value of attending to potential context-based identity-driven experiences for school leader development and support.