The Portrait of Eleanor of Toledo and Her Son is a painting by the Italian artist Agnolo di Cosimo, known as Bronzino, finished ca. 1545. One of his most famous works,it is housed in the Uffizi Gallery of Florence, Italy and is considered one of the preeminent examples of Mannerist portraiture. The painting depicts Eleanor of Toledo, the wife of Cosimo I de' Medici, Grand Duke of Tuscany, sitting with her hand resting on the shoulder of one of her sons.