Breast cancer is the most common forms of cancer and a leading cause of mortality in women. Early and correct diagnosis is, therefore, essential to save lives. The development of diagnostic imaging applied to the breast has been impressive in recent years and the most used diagnostic test in the world is mammography, a low-dose X-ray technique used for imaging the breast. In the first half of the 20th century, the diagnosis was in practice only clinical, with consequent diagnostic delay and an unfavorable prognosis in the short term. The rise of organized mammography screening has led to a remarkable reduction in mortality through the early detection of breast malignancies. This historical review aims to offer a complete panorama of the development of mammography and breast imaging during the last century. Through this study, we want to understand the foundations of the pillar of radiology applied to the breast through to the most modern applications such as contrast-enhanced mammography (CEM), artificial intelligence, and radiomics. Understanding the history of the development of diagnostic imaging applied to the breast can help us understand how to better direct our efforts toward an increasingly personalized and effective diagnostic approach. The ultimate goal of imaging applied to the detection of breast malignancies should be to reduce mortality from this type of disease as much as possible. With this paper, we want to provide detailed documentation of the main steps in the evolution of breast imaging for the diagnosis of breast neoplasms; we also want to open up new scenarios where the possible current and future applications of imaging are aimed at being more precise and personalized.