High prevalence of psychological distress, including greater depression, lower self-esteem, and suicidal ideation, has been documented across numerous samples of transgender women and has been attributed to high rates of discrimination and violence. According to the gender affirmation framework (Sevelius, 2013), access to sources of gender-affirmative support can offset such negative psychological effects of social oppression. However, critical questions remain unanswered in regards to how and which aspects of gender affirmation are related to psychological well-being. The aims of this study were to investigate the associations between three discrete areas of gender affirmation (psychological, medical, and social) and participants' reports of psychological well-being. A community sample of 573 transgender women with a history of sex work completed a one-time self-report survey that assessed demographic characteristics, gender affirmation, and mental health outcomes. In multivariate models, we found that social, psychological, and medical gender affirmation were significant predictors of lower depression and higher self-esteem while no domains of affirmation were significantly associated with suicidal ideation. Findings support the need for accessible and affordable transitioning resources for transgender women in order to promote better quality of life among an already vulnerable population. As the gender affirmation framework posits, the personal experience of feeling affirmed as a transgender person results from individuals' subjective perceptions of need along multiple dimensions of gender affirmation. Personalized assessment of gender affirmation may thus be a useful component of counseling and service provision for transgender women. Transgender women (i.e., individuals assigned a male sex at birth who identify as female, male-to-female, transgender women) are a group at elevated risk of adverse health outcomes (Institute of Medicine, 2011). Numerous studies have reported higher prevalence of psychological distress, including depressive symptoms, low self-esteem, and suicidal ideation in community samples of transgender women (MacCarthy, Reisner, Nunn, PerezBrumer, & Operario, 2015;Operario & Nemoto, 2010). Due to their gender identity or expression, transgender people experience high levels of gender-based social oppression, or transphobia, including everyday discrimination, family rejection, and hate crimes (Bazargan & Galvan, 2012;Bradford, Reisner, Honnold, & Xavier, 2012;Koken, Bimbi, & Parsons, 2009;Lombardi, Wilchins, Priesing, & Malouf, 2002;Nuttbrock et al., 2010). Scholars have proposed that adverse mental health outcomes in transgender populations are a result of this gender-specific social oppression (Bockting, Miner, Swinburne Romine, Hamilton, & Coleman, 2013;Goldblum et al., 2012;Haas et al., 2010;Nuttbrock et al., 2013;Reisner, Gamarel, Dunham, Hopwood, & Hwahng, 2013). Additionally, the traditional sexism and denigration against women and individuals demonstrating characteristics d...