The aim of this study was to explore experiences of homelessness in an affluent university town. Seven homeless men were recruited at a welfare program for homeless people to participate in in‐depth, semistructured interviews that explored their experiences of homelessness in the town. The ages of the participants ranged from 36 to 52 years. There were three White participants, two of mixed race, and two Black participants. Thematic analysis was used to analyze the data, from a bottom‐up systems perspective. The results revealed some of the participants' drug‐related experiences, their structural experiences (e.g., shelter policy, low wages, and the poverty trap), their social experiences (e.g., the loss of their families and the lack of social standards in the homeless community), and their psychological experiences (i.e., fatalism, complacency, and responsibility). Subsidized housing and social grants are unlikely to effectively address the homelessness of men if other components of their experience, such as their drug‐related experiences, their structural experiences, their social experiences, and their psychological experiences, are not attended to.