This study examined gender differences among homeless young adults’ coping strategies and homelessness stressors as they relate to legal (e.g., full-time employment, selling personal possessions, selling blood/plasma) and illegal economic activity (e.g., selling drugs, theft, prostitution). A sample of 601 homeless young adults was recruited from 3 cities (Los Angeles, CA [n = 200], Austin, TX [n = 200], and Denver, CO [n = 201]) to participate in semi-structured interviews from March 2010 to July 2011. Risk and resilience correlates of legal and illegal economic activity were analyzed using six Ordinary Least Squares regression models with the full sample and with the female and male sub-samples. In the full sample, three variables (i.e., avoidant coping, problem-focused coping, and mania) were associated with legal income generation whereas eight variables (i.e., social coping, age, arrest history, transience, peer substance use, antisocial personality disorder [ASPD], substance use disorder [SUD], and major depressive episode [MDE]) were associated with illegal economic activity. In the female sub-sample, three variables (i.e., problem-focused coping, race/ethnicity, and transience) were correlated with legal income generation whereas six variables (i.e., problem-focused coping, social coping, age, arrest history, peer substance use, and ASPD) were correlated with illegal economic activity. Among males, the model depicting legal income generation was not significant yet seven variables (i.e., social coping, age, transience, peer substance use, ASPD, SUD, and MDE) were associated with illegal economic activity. Understanding gender differences in coping strategies and economic activity might help customize interventions aimed at safe and legal income generation for this population.