Osteocutaneous defects of the clavicle follow surgical management of chronic infections, tumors, and trauma. There are several reconstructive options, but it is unknown whether the bone needs to be reconstructed, which flaps are the best for reconstruction, nor why certain flaps favored over other options for a given scenario. Factors such as wound etiology, defect size, patient demographics, and co-morbidities guide therapy. The management of osteocutaneous defects of the clavicle is herein reviewed. Two clinical cases are presented, literature discussing clavicle form and function, disease pathogenesis, and reconstructive approaches are analyzed, and a resultant algorithm proposed.