BACKGROUND: Chest masculinization is aimed at aligning physical appearance of female-to-male (FtM) transgender patients to their identifying gender. Despite limited evidence, obese FtM patients have historically been denied this procedure due to concerns of complications. We reviewed chest masculinization in the high body mass index (BMI) population to analyze the outcomes. METHODS: A Medstar system single surgeon retrospective case review was performed of all FtM patients who underwent chest masculinization from Jan 2018 to Dec 2019 with a BMI greater than 30 kg/m. Primary outcomes were mastectomy-site complications. RESULTS: Twenty-seven obese FtM patients who underwent bilateral chest masculinization were identified. Mean BMI was 39.2 kg/m (SD 5.2). Preoperatively, the majority of patients had a cup size of D or larger (77.3%) and grade 3 ptosis (80.0%). Overall rate of complications was 31.5% at median follow-up of 2.1 months. Individual complications included: partial nipple graft loss 18.5%, total nipple graft loss 5.6%, seroma 3.7%, hematoma 3.7%, infection 2.9%. No complications necessitated return to the operating room. However, the majority of patients (77.8%) were completely satisfied with their aesthetic outcome. CONCLUSION: Mastectomy can be safely performed for chest masculinization in obese FtM patients. The rate of acute complications is comparable to that of non-obese patients despite a mean BMI near 40 kg/m in this case series. A safe procedure with high satisfaction, obese FtM patients should not be excluded from the increased quality of life and dysphoria reduction chest wall masculinization offers.