The psychological challenges associated with gender identity in developing countries like India are only recently receiving research attention. The study aimed to understand self-esteem, perceived social support, and depression among trans men in India. A comparative analysis was also undertaken between those who have and have not undergone sex reassignment surgery. The sample comprised 30 trans men, out of which 15 had undergone sex reassignment surgery and 15 had not. The Multidimensional Scale of Perceived Social Support, Rosenberg Self-esteem Scale, and Beck’s Depression Inventory-II were used. Perceived social support from family and friends was found to be a significant predictor of self-esteem. Support from all three sources—family, friends, and significant others significantly predicted depression among the total sample. Trans men who had undergone sex reassignment surgery, reported higher self-esteem and lower depression levels, as compared to those who were yet to undergo surgery. The findings highlighted the contribution of social support in fostering the mental health of trans men. The consequent psychological benefits of surgery were also demonstrated. The study has implications for planning and designing mental health interventions for this community.