This article traces links between subjectivity, peer relations and neighbourhood risk for a group of boys living in an area of London with high levels of crime, gang activity and socio-economic inequality. Drawing on data from a qualitative study of young people and neighbourhood risk, we use a psycho-social approach to analyse how gendered subjectivities are shaped by the specific social context. We found that tough masculinities were performed by boys across different social arenas of school, neighbourhood and in the context of a weekly research group. But the boys were also troubled by these masculinities, and their own engagement in data analysis illuminated some of their fears. While the tough masculine ideal is revealed often to be a masquerade, it nevertheless exerts a powerful and pernicious influence over the subjectivities of young men trying to navigate safely through a context of everyday risks.