Portrait of Eleanor of Toledo is a painting by Bronzino of Eleanor of Toledo, a Spanish noblewoman who was the duchess consort of Cosimo I de' Medici, Grand Duke of Tuscany, and her son Giovanni. The painting is one of the artist's most famous works and is in the Uffizi Gallery in Florence, Italy. It is the first known state-commissioned portrait to include the ruler's heir, which was done in part because Cosimo's predecessor Alessandro died without any legitimate male heirs. The boy's inclusion implies that Cosimo's rule would bring stability to the duchy.