Gynecomastia is the most common cause of breast enlargement in males. Trichophyton rubrum is a common dermatophyte, is responsible for a variety of infections, and may rarely manifest as a dermatophytic pseudomycetoma. We report the case of a 52-year-old man who presented with progressive bilateral breast enlargement. This is the first reported case of bilateral breast pseudomycetoma due to T. rubrum. Long-term antifungal therapy with itraconazole was successful.