Breast reconstruction is highly complex, requiring navigation of not only clinical and operative realities, but of patient expectations as well. The authors sought to identify historical art pieces that exhibit breast asymmetries and deformities for comparison with photographs of breast reconstruction patients seen at the clinic of the senior author (S.O.P.) to demonstrate that achievement of perfect breast cosmesis is challenging in both breast reconstruction and in the classical arts. Open access libraries and Creative Commons images were reviewed to identify appropriate works of art from various time periods and geographic locations. Following artwork selection, photographs of breast reconstruction patients were reviewed and paired with selected artworks exhibiting cosmetically similar breasts. A total of 8 pieces of selected historic art were found to have at least 1 matching patient photograph, with 9 correlative patient photographs ultimately chosen. Common breast asymmetries and deformities identified included ptosis, asymmetric chest wall placement, asymmetric nipple placement, and absence of the nipple. This review identified diverse artworks of varying styles spanning vast expanses of both geography and time that exhibited breast deformities and asymmetries commonly encountered in patients seeking revision of breast reconstruction. This underscores that creating the cosmetically ideal breast is difficult both in the operating room and the art studio. Importantly, the authors emphasized that the arts frequently celebrate that which is considered beautiful, although to the trained eye of a plastic surgeon that which is considered beautiful is often classified as dysmorphic or asymmetric.