Despite the significant progress made in the past several years in pharmacotherapies for skin cancer, such as BRAF/MEK inhibitors, immune checkpoint inhibitors, and Hedgehog pathway inhibitors, surgical removal of primary skin cancer is still the first choice of treatment unless distant metastases are evident. In cases of lymph node metastases with clinically palpable lymphadenopathy, lymph node dissection (LND) is typically performed for most skin cancers. In the surgical treatment of primary skin tumors, the surgical margin is critical not only for reducing the possibility of tumor recurrence but also for minimizing the cosmetic and functional complications associated with wide local excision. In contrast, dermatologic surgery can cause various complications. Although skin graft is frequently used for reconstruction of the surgical defect, extensive graft necrosis may develop if optimal stabilization of the graft is not obtained. LND also sometimes causes complications such as intraoperative or postoperative bleeding and postoperative lymphoceles. Moreover, as in other types of surgery, surgical site infection, intraoperative anxiety, and intraoperative and postoperative pain may also develop. These complications are frequently associated with significant morbidity and discomfort. In this review, we summarize the evidence from previous clinical studies regarding the optimal surgical margin for skin cancer and the methods for diminishing the complications associated with dermatologic surgery.