Few cases of naevoid hyperkeratosis of the nipple and areola (NHNA) have been documented since the condition was first described in 1923. A recent PubMed search (Mar 2014) yielded 107 cases of NHNA in the world literature, mostly female patients with adolescent-onset disease. We report the first two cases of adolescent-onset NHNA from the Philippines. To our knowledge, these are also the first two cases of extensive bilateral NHNA reported in which the lesions have extended beyond the areolae affecting the surrounding periareolar skin, covering almost the entire breast. Medical treatment of NHNA has been commonly associated with treatment failure or recurrence after treatment cessation, requiring intermittent therapy. However, our two cases had successful outcomes with medical treatment using a combination topical steroid/salicylic acid ointment with > 2 years of follow-up.