An improved post-operative dressing for providing both breast and, notably, nipple reconstruction and which in particular establishes custom lateral supporting of the nipple annulus. A body is constructed of a medical grade silicone and exhibits a three dimensional shape adapted for placement over the reconstructed breast and an aperture defined by an inner rim configured within the body is adapted to seat therethrough an associated nipple graft or flap in a laterally supporting and non-pressure applied fashion. The dressing may include a controlled release transdermal delivery system for administering at least one medicinal drug directly to the breast mound and/or nipple.