Franciscan iconography is examined within the context of artistic developments over time, and Franciscan documents that address the curious phenomenon surrounding the representational images of Francis of Assisi. Comparisons of diverse images of Francis will be the focus of our inquiry that reveals a visual history often based in Franciscan literature, yet uniquely aligned with the discipline of secular painting of the time. Post-Reformation images of Francis of Assisi are examined chronologically for content and context as they relate to the continued growth of the Franciscan Order. Iconographical elements of images of Francis that reflect the Franciscan lifestyle are compared and contrasted with images of the secular world of the same time periods, as secular iconography aggressively exerts its influence and tradition upon