Background Among individuals experiencing homelessness, unsheltered status is associated with poor health and access to care and an increased risk for premature death. Insufficient research has explored gender differences in these outcomes; the objective of this study was to address this gap in the research. Methods This study used survey data collected during the 100,000 Homes Campaign. Chi-square tests identified differences in the characteristics of women, men, and transgender individuals. Generalized linear mixed models fit with demographic, homelessness, mental/behavioral health, institutional, and income characteristics were run separately for women and men to assess correlates of unsheltered status and increased risk of premature mortality. Results Men reported more frequently experiencing unsheltered homelessness while women and transgender participants more frequently met the criteria for risk of premature mortality. Women reported less frequently than men a history of or current substance use, but it significantly increased their likelihood of unsheltered homelessness; reports of mental health issues were rarer among men but significantly increased their odds of unsheltered homelessness. The experience of a violent attack while homeless was most strongly related to increased risk of premature mortality for both women and men. Conclusions Interventions to reduce unsheltered homelessness among men should be particularly sensitive to mental health issues while for women there may need to be increased attention to substance use. A focus on experience of trauma and the provision of trauma-informed care is essential to address the increased risk of premature mortality among both men and women experiencing homelessness.