Research to date has given little attention to differences in the experience of youth homelessness by ethnicity. This article provides a comparative descriptive analysis of the effect of differences and similarities in paths to homelessness, self-perception, and survival strategies on health behaviors and consequent health outcomes of African American and white homeless youth in San Francisco, USA. We conducted participant observation and ethnographic interviews with 54 youth primarily recruited from street venues. Hypotheses generated from the ethnographic data were validated in between-group analyses using concurrent epidemiological data collected from a sample of 205 youth. Our samples of unstably housed African American and white youth, though sharing common histories of family dysfunction, differed in both the ethnographic accounts and epidemiological analyses in their experiences of family, access to housing, street survival strategies, self-presentation, health behaviors and service utilization. Our sample of white youth generally identified with the term “homeless,” engaged in survival activities associated with such a label, and accessed the services intended to address the needs of homeless youth. In contrast, our sample of African American youth generally did not perceive themselves as “homeless,” a stigmatized term, and were thus less likely to utilize, or be accessed by, relevant services.