We report on four children born with medium to large congenital melanocytic nevi (CMN) with color heterogeneity and irregular surface rugosity. As these patients aged, their nevi evolved to become more homogeneous and lighter in color, and developed a smoother, more even texture. We propose that given this evolution toward benignity, conservative monitoring and management may be appropriate even in the context of atypical-appearing features at birth. Such knowledge regarding the evolution of these CMN can more accurately guide parents and clinicians in determining whether to biopsy or remove an atypical-looking lesion early in life for medical or cosmetic reasons.