With figures painted in sensuous curves and a generous use of gold leaf, this small panel is a beautiful example of Sienese Renaissance painting. While Florentine art of this period reflected innovations in portraying the world more naturalistically, artists in Siena, only about twenty-five miles away but in a separate city-state, still worked in a style that recalled religious art from a much earlier time. Poses remained stylized, and the gold leaf backgrounds still were decorated with punchwork, but the works had no less spiritual beauty than their counterparts in Florence.
Matteo de Giovanni was one of the most successful Sienese painters of the late fifteenth century. His paintings combine a nascent search for plasticity and realistic anatomical structure with the stylized grace and preciousness favored by his Sienese patrons. This remarkably well-preserved piece was probably commissioned as a private image for the spiritual inspiration of an individual. The Augustinian Saint Nicholas of Tolentino, to the right of the Virgin, is often featured in Sienese painting, suggesting that he may have had local followers. Devotion to Saint Anthony, shown on the left, was more widespread, but his presence here may also have held a special meaning for the patron of the picture.