ABSTRACT This paper narrates an induction process about how adolescents and young men are drawn into living and practising a distinctive and often violent cultural form of street masculinity on an inner-city estate in London. The paper sets out to counteract dominant discourses which often portray young black men from working-class and impoverished backgrounds as ‘hypermasculine perpetrators of violence’. Developing the concepts of caring and personalized masculinities shows that, in the right conditions, young men exercise agency to perform different masculinities in different contexts and times, fashion more inclusive identities, and create new trajectories and lifestyles. The ethnographic fieldwork took place over nine months in 2019. It involved around 50 young men who were Black, Asian and minority ethnic. The paper focuses on two particular young men, aged 19 and 22, who appear as exemplars of ways of enacting different patterns of masculinity.