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 photos of breast reconstruction patients seen at the clinic of the senior author to demonstrate that achievement of perfect breast cosmesis is challenging in both breast reconstruction as well as 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, photos of breast reconstruction patients were reviewed and paired with selected artworks exhibiting cosmetically similar breasts. A total of 9 pieces of selected historic art were found to have at least one matching patient photo, with 11 correlative patient photos 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 exhibit 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 emphasize that the arts frequently celebrate that which is considered beautiful, though to the trained eye of a plastic surgeon, that which is considered beautiful, is often classified as dysmorphic or asymmetric.