The scion of a distinguished Milanese bourgeois family, Piero became part of Milan's lively literary milieu at an early age. Frequenting the same circles, Colacicchi and Piero came into contact in 1927; it was the beginning of a long friendship that was to bind them for the rest of their lives.

As the date indicates, the portrait was painted during the years of the Second World War, when their respective families spent holidays in Forte dei Marmi, and it is clearly influenced by Colacicchi's passionate studies of 15th-century Florentine painting during the years in which the painter was hosted by Bernard Berenson in Vallombrosa at the Casa al Dono; studies that led him to publish, in 1943, one of the first monographs on the painting of Antonio Benci - Antonio del Pollaiuolo.