Homelessness among older adults is a growing global phenomenon, with men disproportionately affected compared to women. This study uses a life-course approach to examine the intersection of age and gender as reflected in older men’s experiences of homelessness. Drawing on semi-structured interviews with older men living in transitional housing in a major Czech city, it explores how the situation of homelessness shapes the way older men “do” gender and experience ageing, and how categories of gender and age intertwine in men’s actions and self-conceptions. The article outlines three main themes of intersectionality: liminality and ageism in temporal housing; breadwinner expectations and gendered social embeddedness; masculinity and able-bodiedness. By focusing on older men’s experiences of major life transitions, this research addresses a gap in the study of men, ageing, and homelessness within the post-socialist context of Czech society.