BACKGROUND: Societal awareness of transgender individuals has led to increased acceptance and demand for sex-confirming surgery. In female to male transsexuals, the most common procedure is removal of breast tissue to masculinize the chest. METHODS: Eighty-eight transgender patients underwent either a subcutaneous nipple-sparing mastectomy (NSM) with or without a periareolar mastopexy or nipple reduction, or bilateral mastectomies with free nipple grafts (MFNG) with or without nipple reduction. Surgical techniques are discussed. Demographic data, use of testosterone, specimen weights, rates of wound dehiscence, infection, hematoma, hypertrophic scars, nipple loss, and revision surgery were all assessed. RESULTS: Of the 88 patients in the study, 40 underwent NSM and 48 underwent MFNG. Patients undergoing NSM were 4.1 times more likely to have a hematoma compared with patients undergoing MFNG (P <0.05). Mastectomy weight was not correlated with the occurrence of hematoma (P >0.80). Only 1 patient who underwent NSM required revision, whereas 5 patients in the MFNG patient population underwent revision. Patients were more likely to have hypertrophic scarring with the MFNG technique (0% vs 25%, P < 0.01) There were no infections, no wound dehiscence, and no nipple loss in any patient. Eighty-three percent of the patients who responded to a satisfaction survey (57/88) were very satisfied with their result, and 100% would recommend this procedure to other transgender individuals. CONCLUSIONS: Female to male transgender mastectomy can be performed with low complication rates and high satisfaction. Nipple-sparing mastectomy were more likely to have a hematoma than patients undergoing MFNG.