The term “nevi of special sites” refers to melanocytic nevi of specific anatomic locations including the breast, axillae, umbilicus, genitalia, flexural areas, acral surfaces, ear, scalp and the conjunctiva. Nevi from these anatomic sites display sometimes dermoscopic and histological features of melanoma, resulting in unnecessarily high rates of excisions and re-excisions. Some authors have categorized nevi excised in the axillary, breast, umbilical and perineal areas as the nevi of the milk line. Two patients, a 32-year-old female and 23-year-old male with breast and periumbilical pigmented lesions, presented to our Department during 2017. Dermoscopy revealed features that were highly specific for melanoma. Excisional biopsies were done and histopathology revealed benign nevi with present site-related atypia. Irregular blotches, non-uniform radial streaks, blue-gray veil, and regression are the most specific features of melanoma of the breast and flexural areas. Excision is always recommended in pigmented lesions on the breast and flexural areas, which exhibit these features. However, larger studies are needed to define specific criteria required to distinguish special-site nevi from melanoma.