More like this
Domenico Ghirlandaio — Portrait of a Man
Sandro Botticelli — Portrait of a Youth
Biagio d'Antonio — Portrait of a Boy
Attributed to Antonello da Messina — Portrait of a Young Man
Giovanni Bellini — Portrait of a Young Man in Red
Andrea Mantegna — Rodolfo Gonzaga (1451–1495)
Florentine 15th Century — Profile Portrait of a Young Man
Biagio d'Antonio — Portrait of a Young Man
North Italian 15th Century — Profile Portrait of a Boy
Tyrolean 15th Century — Portrait of a Man
Maestro delle Storie del Pane — Portrait of a Man, possibly 
Florentine 15th Century — Matteo Olivieri (?)