Rosso Fiorentino, 'Portrait of a Young Man holding a Letter', 1518

A young man glances up at us from the letter he has just been reading. He wears a black watered silk jacket with large damask sleeves. His expensive yet sober costume suggests that he is a man of wealth and status, perhaps with literary or political interests.

This is the earliest of about five portraits generally agreed upon as being by Rosso Fiorentino and the only one that is precisely datable. It was painted in Florence when he was about 24, while he was in the workshop of Andrea del Sarto. Sarto was away in France at the time, which opened up opportunities for other artists to take on new commissions. The pared-back setting, restrained colour palette and the sense of a private moment interrupted in Rosso’s portrait is comparable to Sarto’s Portrait of a Young Man, of about 1517–18.

The portrait reveals something of Rosso’s eccentricity, particularly in the strange spiky fingers, the curiously abstract style and the characteristically swift way of working the paint. More than any of his Florentine contemporaries, Rosso allowed his brushstrokes to remain visible rather than blending them. The facial features are made up of hasty brushstrokes applied in hatching and cross-hatching. There appears to be no underdrawing, suggesting that the portrait may have been swiftly painted from life. A few changes were made to the composition during painting, notably in the sitter’s hands and around the edges of the letter; originally more of the youth’s elegant white shirt was covered up by his black coat. Although the portrait is not signed, the distinctive manner in which it is painted is as good as a signature. The features of the face all but dissolve when viewed close up, but the sketchy brushstrokes blend into a powerfully convincing and memorable likeness when seen from a distance. This approach is also a feature of Portrait of a Knight of Saint John by Rosso.

The unidentified young man glances up from a letter dated 22 June 1518, which suggests that this date may have been of special significance to him. The letter bears further traces of writing which may provide clues to his identity, but they are extremely difficult to read and have yet to be deciphered. The part of the letter closest to the fingers of his right hand appears to include his name, as the writing here would have been on the outside of the letter when folded. The single word barely visible between his fingers was probably his address. The wax seal is stamped with the lily of Florence.

The man’s gaze is at once dreamy and penetrating, as though we have momentarily interrupted his reading and his thoughts are still on the contents of the letter. This sense of psychological realism and immediacy was only just beginning to find a place in portraiture at the time the work was painted, appealing to the rising class of wealthy and intellectual patrons.

The free technique and abstract forms displayed in this excellently preserved portrait heralded a new style of painting. At first Rosso’s approach proved too radical for many potential patrons, so he worked mainly outside his native city of Florence, finding employment initially elsewhere in Tuscany, and then in France. But it was for unconventional images like this that Rosso eventually became celebrated.