Leoni is celebrated for his fresh and immediate portraits of early 17th Century Roman society. Baglione, in his biography published in 1642, records that the artist was encouraged in this direction by his father, also a portraitist, and that 'there was no one of his age in this art who could equal him' (quoted in J.T. Spike, Baroque Portraiture in Italy: Works from North American Collections, exhib. cat., Sarasota, John and Mable Ringling Museum of Art, and elsewhere, 1984-1985, p. 12). From about 1614, the year he was elected Principe of the Accademia di San Luca, Leoni began to number his portraits in the lower left corner: the highest number recorded thus far is 434, drawn in September 1629, a portrait of Settimia Manenti Salernitana now in the Pierpont Morgan Library, New York.
The present drawing is unusually early for a portrait by Leoni. A closely comparable Portrait of a boy, dated 1609, was sold in these Rooms, 6 July 1999, lot 101.