Acquired by the Gallerie in 1856 along with a group of works from the Manfrin collection, this Portrait of a Young Man is closely affiliated to the portrait prototypes of the “Flemish style” perfected by Antonello da Messina, to whom this painting was long attributed. An important figure in Flemish painting of the second half of the fifteenth century, Memling was also much appreciated in Italy, thanks to interest expressed by such important people as the Medici and, in Venice, the cardinals Bembo and Grimani. Considering his clothes and hat as well as his singular haircut, the young man might have been an Italian merchant operating in Bruges, where he was able to commission the famous artist to paint his portrait. The contrast between the extremely close-up and detailed image, almost as if the man is leaning over an invisible balustrade on which he has rested his hand, and the landscape in the background, which is more generic and miniaturist and evokes a far-away distance, provide a model that was to be largely followed in Italian painting of the second half of the fifteenth century, and above all in Venice.