Background: Fixed drug eruption (FDE) is a common cutaneous disorder which develops within hours of taking the offending drug and recurs at the same site with subsequent exposure to the same drug. Non-steroidal anti-inflammatory drugs (NSAIDs) are common offending drugs. Methods: A 14-year-old girl initially presented with a 1-year history of a recurrent reddish-brown plaque around her right areola. The lesion became pruritic and raised during menses, and subsided during the remainder of her menstrual cycle with the exception of persistent residual hyperpigmentation. The patient had a pattern of naproxen use during menses for dysmenorrhea. Results: The skin biopsy specimen revealed focal bullae formation and scattered necrotic keratinocytes in epidermis, hydropic degeneration of the basal cell layer, pigmentary incontinence and a perivascular infiltrate composed of lymphocytes and eosinophils. These changes confirmed the diagnosis of fixed drug eruption. Conclusion: Fixed drug eruption to nonsteroidal anti-inflammatory drugs is common. However, FDE due to naproxen, one of the NSAIDs, is rarely reported. We describe an unusual case of FDE, which recurred at each menses.