Daughter of viceroy of Naples Don Pedro di Toledo, Eleonora married Cosimo I de' Medici in 1539 and died in 1562. In this picture, datable around 1545, she is portrayed with one of their eight sons, the young John, born in 1543 and died, as his mother of malaria, in 1562. The intense blue of the background and the stateliness of the figure enhance the preciousness of Eleonora's dress (for long time, erroneously believed her sepulture cloth), while her aristocratic beauty betrays a sense of melancholy.

　It was painted towards 1545, at the happiest moment of Bronzino's activity as a portrait painter. The diligent and frankly enjoyed description of the details of the costume are transfigured, through the geometrical simplification and the calm fixity of the light, into a vision of an almost ecstatic detachment.

　Archeological work in the tomb of Eleonora, the wife of Cosimo I de' Medici, has revealed fragments of the dress worn in this portrait.

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　This precious painting, documented by Vasari, depicts the Dutchess of Florence, Eleonora di Toledo, with her little son Giovanni. It was painted in 1545 by Bronzino, who was a student of Pontormo and the court portrait artist of the Medici. In spite of the official nature of the portrait, seen through the very refined clothing and the splendor of the jewelry, Bronzino joins the figures of the mother and child in an affectionate pose creating one of the masterpieces of European Portraiture of the 16th century. The painting has been in the Tribune since 1620.

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