Pinturicchio (Bernardino di Betto), Portrait of a Boy c. 1480-82 Oil and tempera on poplar wood. Gemäldegalerie, Dresden

The serious and somber-looking young Venetian patrician wearing a red doublet and a slightly tilted blueish cap with a partially bent brim.

Unknown Author from the Circle of Alvise Vivarini, Portrait of a gentleman, bust-length c. 1480-1500 Tempera on panel. Private collection. The slightly cropped portrait depicts a young Venetian patrician with the zazzera hairstyle --fashionable in Venice during the 1480s and 1490s-- and a brimless red cap covering the top of the head, but not the forehead.

Andrea da Murano, Saints Sebastian, Vincent Ferrer, Roch, and four others with St Peter and the Madonna della Misericordia c. 1475 Tempera on wood. Gallerie dell'Accademia of Venice Originally a triptych decorating the church of San Pietro Martire on Murano. The detail shows Saint Roch (1348-1376/9) wearing a pilgrim's wide-brimmed hat decorated with the scallop shell emblem, associated with the pilgrimage to the Santiago de Compostela, a leading Catholic pilgrimage site since the ninth century.

Vittore Carpaccio, Departure of the Ambassadors The Legend of Saint Ursula cycle 1497–98 Oil on canvas Gallerie dell'Accademia, Venice Originally created for the Scuola di Sant'Orsola (Ursula) in Venice.

Detail showing the selection of fashionable hats worn by the viral youth observing the farewells of the pagan ambassadors to the Christian king of Brittany. Some of the youth have their hats tilted to the side, reflecting a trend in late 1490s fashion in Venice.

Antonio Vivarini, Polyptych of Saint Peter Martyr: St Peter Martyr Healing the Leg of a Young Man c. 1450 Tempera on wood. Metropolitan Museum of Art, New York Originally a part of an now-dismantled polyptich thought to have originally contained fourteen scenes and houses in the basilica San Zanipolo (Santi Giovanni e Paolo) in Venice.

Detail of the head of the Young Man whose leg is being healed by St Peter Martyr (1205-1252) after he had cut off his own leg in remorse for kicking his mother.

Pietro Perugino, Christ Giving the Keys to St. Peter c. 1481-82 Fresco located at the Sistine Chapel, Vatican Full image at Wikipedia.

Detail showing Italian men in contemporary dress to the right of the Apostles flanking Christ.