Research on employment segregation & women's lower earnings has predominantly focused on labour-market participants. Marginal groups such as the homeless have therefore been excluded from theory & research on work-related gender segregation. In order to fill this void, this paper explores how income creation among homeless youth from Toronto, Canada varies according to gender. Based on questionnaire and interview data our results show that, in relative terms, males are involved in the more financially lucrative sectors of the street economy. We frame the analysis of our findings in terms of a broader discussion of how homelessness is gendered within the spaces and places homeless youth occupy.