Lichen planus is a chronic inflammatory disorder affecting skin and mucosal surfaces. There are multiple variants of lichen planus described in the literature. We report a case of inverse lichen planus in a healthy 50-year-old male who presented to our dermatology clinic with multiple violaceous to hyperpigmented patches affecting both axillae and groin for three months. A skin biopsy confirmed the diagnosis of lichen planus. The patient subsequently developed nail dystrophy affecting his fingernails consistent with nail lichen planus. Early recognition and treatment of nail lichen planus is important to prevent irreversible scarring.