Breastfeeding is thought to be the most optimal form of infant nutrition. Nursing mothers are generally advised to continue breastfeeding until the infant is two years of age or beyond. Unfortunately, however, a majority of nursing mothers will discontinue breastfeeding much earlier than recommended. The most common reason for early discontinuation of breastfeeding is nipple pain. It is, therefore, essential that dermatologists know how to appropriately diagnose and effectively treat nipple pain associated with nipple dermatitis among nursing mothers. This review article provides a detailed discussion on the clinical features and management of various causes of nipple dermatitis during lactation, including problems with infant latch-on, congenital oral anomalies, plugged lactiferous ducts, atopic dermatitis, irritant contact dermatitis, allergic contact dermatitis, yeast infections, bacterial infections, herpes simplex virus, and Raynaud’s phenomenon of the nipple.