Probably by Girolamo Macchietti, A Knight of S. Stefano

The sitter wears the red cross of the military order of S. Stefano, founded in Pisa in 1561 by the Grand Duke of Tuscany, Cosimo I de‘ Medici. He stands in a very grand room that appears to be his library, beside a large table supported by a carved winged figure holding a swag of flowers. The atmosphere of learning suggests that the winged figure is a ’genius' rather than a cherub. The lower walls of the room are panelled in wood and behind the sitter’s head there appears to be a niche containing a monochrome sculpture group of a woman and child. We only see the lower part of the sculpture, which may relate to the sitter’s identity. Several books of various sizes are propped up on the ledge and against the niche.

The man stands looking directly at us in a confident pose, with one hand on his hip, the other resting on a book. He is brightly lit from the front, resulting in a clear, sharply defined image. The picture’s low viewpoint means that the man looks down at us, emphasising his authority – he was clearly an important member of the order. His voluminous black cloak dominates the composition, its elaborate damask lining only becoming apparent when you look closely. The letters, pen and Mannerist inkstand on the table, and the books and statue above, allude to his status and learned interests. A very similar bronze inkstand is in the collection of the Victoria and Albert Museum, London. Such an object, as well as being functional, would also have been regarded as a work of art in its own right.

Although Moretto and Moroni were painting full-length portraits of the nobility in Brescia at this time, independent life-size and full-length portraits are less common in Tuscan sixteenth-century art. The painting was once thought to be by Alessandro Allori (1535–1607), successor to Bronzino as painter to the Medici court in Florence. Allori painted countless portraits of such upper-class Tuscans, and the elaborately carved table in this picture is typical of his works. However the painting is closer in style to the work of Girolamo Macchietti, a Florentine artist who also painted The Charity of Saint Nicholas of Bari.