The objective was to estimate the prevalence of melanocytic nevi (MN) in children and to determine their dermoscopic characteristics and relationship with anatomic location and environmental and constitutional factors. The population was a randomly selected sample of 144 children who attended primary schools in Naples, Italy. Before physical examination of the children, standardized interviews were conducted with their parents. Follow-up interviews of both the children and parents were conducted 1 year later. Photographic and dermoscopic images were obtained. Boys had more MN than girls; 465 MN (55.6%) were observed in boys and 371 (44.4%) in girls (p < 0.05). The trunk and neck were the most common locations of MN (p < 0.001). The main dermoscopic feature of all MN observed was a globular pattern (p < 0.001). A significant correlation between duration of sunbathing and MN counts was revealed (p < 0.05). At 1-year follow-up, 118 new MN were identified in 66 children. The trunk and neck areas were the most common regions involved in the appearance of new MN (n = 68, 57.6% of all new MN, p < 0.001). The new MN count was significantly higher in children who reported more sunbathing (p < 0.001). Changes in the dermoscopic pattern were observed in 45 persistent MN, demonstrating more MN with a reticular-globular pattern, especially on the trunk, neck, and upper extremities (p < 0.001). MN development in early life is the result of complicated relationships between nevus evolution, anatomic location, and environmental and constitutional factors.