Background Gynecomastia is a common finding in males. Clinical aspect varies widely in world populations showing peculiar hallmarks according to different body shapes reflecting personal expectations; therefore, a surgical plan must be tailored on individual basis to all type of patients. Materials and Method A total of 522 patients, treated for bilateral gynecomastia from January 2007 to January 2019, were included and reviewed in this retrospective study. Considering physical status BMI, muscular trophism, hypertrophy of the mammary region, nipple-areola disorder, gland and skin cover consistency, a four-tier classification system has been used to classify the deformity and to assess a surgical plan. In all cases, a subcutaneous mastectomy was performed under direct vision. Results No recurrence of the deformity was observed as well as major complications such as necrosis, and high level of satisfaction was observed in all groups. No breast cancer was found at the histological examinations Operative time ranged from 25 minutes up to 120 minutes and hospitalization time ranged from 1 to 3 days. Conclusion Since the physical status is strictly related to the clinical features of the disorder, a comprehensive classification system and a reconstructive algorithm are proposed.