Contemporary management of gynecomastia includes transareolar excision of gland, disruption of inframammary fold, ultrasonic-assisted lipoplasty with muscular definition, bipolar radiofrequency tightening, pedicled NAC mastopexy with boomerang pattern excision and J torsoplasty, NAC grafts with hockey stick excision pattern, and pectoralis muscle lipoaugmentation. Therapeutic options are arranged across a modified Simon classification. The aesthetic goal is near total glandular reduction, with proper position and shape of the nipple areolar complexes, and masculinity with skin adherence reflecting musculoskeleton. Clinical cases demonstrate these multiple approaches, successes, and pitfalls. Complications relate to delayed healing caused by excessive closure tension or inadequate or inappropriate treatment.