Reconstruction of the lateral mandibular defect presents a complex challenge to the reconstructive surgeon, often involving interconnected soft-tissue and bone requirements. This review examines the current literature on functional outcomes of lateral mandibular reconstruction and presents an algorithm on selecting an optimal reconstructive choice for patients with lateral mandibular defects resulting from oncologic ablative surgery or trauma. PubMed and Medline searches on reconstructing lateral mandibular defect were performed of the English literature. Search terms included lateral mandibular defect, outcomes of mandibular reconstruction, and free flap reconstruction of mandible. Although most of the articles presented are retrospective reviews, priority was given to the articles with high-quality level of evidence. Restoration of function, including speech and swallow, and acceptable cosmetic result are the primary objectives of lateral mandibular reconstruction. When reconstructing the mandible in a patient following tumor extirpation, the patient’s overall prognosis, medical comorbidities, and need for adjuvant therapy should be considered. In the patient with aggressive malignant disease and a poor prognosis, a less complex reconstruction, such as soft-tissue flap with or without a reconstruction plate, may be adequate. In a dentate patient with favorable prognosis, a durable reconstruction, such as osseocutaneous microvascular free flap, is often preferred. Various reconstructive options are available for patients with lateral mandibular defects. Depending on the predominance of the soft-tissue or bony components of the defect, with consideration of the patient’s characteristics and functional and aesthetic goals, the surgeon can wisely select from these reconstructive possibilities.