The gender gap in adolescent mental health experiences is notable, with gender adding an additional layer to the already complex experience of being a young person who is experiencing homelessness. Yet, research in this area is limited. The purpose of this qualitative, interpretive description study was to understand how gender shapes the mental health of youth who are experiencing homelessness in the Niagara Region of Ontario, Canada. Eleven young people between the ages of 16 and 24 were recruited from a youth shelter and participated in individual semi-structured interviews. Thematic analysis and Gender-Based Analysis Plus was used to analyze the data, and findings revealed four contextual factors that appear to influence a young person’s mental health while homeless but that is experienced differently depending on one’s gender identity. These factors are: (1) housing acquisition is challenging, (2) physical presentation is meaningful, (3) cleanliness and hygiene are expected, and (4) utilizing mental health resources is complicated. Additionally, the many strengths that the youth identified and demonstrated in navigating their circumstances are highlighted in the results. These strengths involve (1) exhibiting resilience, (2) expressing the ability to survive, (3) imagining a world that is better, (4) articulating their needs, and (5) drawing on their social connections. The gendered lens that guides this study provides a challenge to the homogenous way that young people experiencing homelessness are often portrayed within the literature. Intersecting identities that include gender and age need to be considered within the mental health-related experiences of youth who live with homelessness. Ensuring that interventions are tailored to meet young people’s specific gendered needs is both a matter of human rights and health equity. Practical implications for service providers are discussed.