The purpose of this study is to describe an anatomic classification system for upper extremity contour deformities and present a novel surgical procedure for management of severe brachial ptosis that may extend from the chest wall to the olecrenon. This clinical report is based upon a series of patients that lost massive amounts of weight following barriatric procedures. A technique of sinusoidal excision in the posterior medial arm position, combined with a generous Z-plasty to restore axillary contour, is outlined. Our results demonstrate a final surgical scar that lies along the posterio-medial aspect of the arm, where it is relatively well hidden when viewed from either the patient’s front or back with the arms at rest. Normal lasting contour of the axilla is achieved. The sinusoidal type pattern used for the skin incision reduces the possibility of straight-line linear contractures, and its more posterior placement makes the resultant scar less noticeable to the patient. This is in contrast to the typically described location along the medial bicipital sulcus, where the scar is more visible when viewed from the front. In conclusion, the described surgical approach provides excellent overall extremity contour with favorable scars, while simultaneously addressing axillary contour deformities.