Masculinities are organised hierarchically, and how a man sees himself is often informed by his positioning within this hierarchy. The context within which men are located determines which factors or markers of masculinity become more salient at different times, and so do the social situations and spaces men are interacting within, and with whom they are interacting. Their socio-cultural, political, and economic positioning inform not only how they construct their gendered identities, but also where they are located within social hierarchies of masculinity. This article examines constructions of masculinities among economically marginalised men who seek work on the side of the road in Cape Town, South Africa. In-depth qualitative interviews were conducted with 10 Black African men and the findings suggest that economic provision remains a central feature in participants’ constructions of masculinity. Men’s experiences of precarious work not only impact how they see themselves but also their ability to establish and maintain romantic relationships which, as argued in this study, serve an important role in validating and affirming participants’ masculinity. This study shows that when some men are not able to provide, their romantic relationships fail, which adversely impacts their self-esteem. In response, some of the participants in this study turned towards alcohol abuse, and neglecting/abandoning their homes and families as a way to avoid the shame and humiliation they experience as ‘men who cannot provide’.