Pilomatrixomas are uncommon benign skin neoplasms arising from the hair follicle matrix. They occur more commonly in children than adults. Most originate on the head, neck, or upper extremities, less commonly on the trunk or lower extremities, and very infrequently in the breast. We present a rare case of pilomatrixoma of the breast in an adult male. As the patient had a strong family history of breast cancer, a full work-up of the breast mass was performed. Ultimately, an excisional biopsy was carried out for patient reassurance.