Ginevra is known to have had several admirers who composed poetry in her honor and entreated her to share own verse with them. Among them was Lorenzo de’Medici, whose elite family was known for its art patronage. Even more significant to Ginevra was Bernardo Bembo, the Venetian ambassador to Florence. It may have been he who commissioned her portrait to celebrate—and substitute for—the object of his admiration and esteem. The painting’s reverse side, Wreath of Laurel, Palm, and Juniper with a Scroll inscribed Virtutem Forma Decorat, is an image of Ginevra’s emblem or impresa and offers another kind of “portrait.” The central juniper, ginepro in Italian, a cognate of Ginevra’s name and thus her symbol, also represents chastity. The palm (right) stands for moral virtue, while the laurel (left) indicated artistic or literary inclinations. Palm and laurel also appear in Bembo’s emblem, and infrared examination of the painting’s layers has also revealed Bembo’s motto, Virtus et honor (virtue and honor), painted beneath Ginevra’s scrolling motto which encircles all three elements and means “Beauty adorns virtue.”
An early work, completed when Leonardo was 21, the painting shows an incipient genius and was revolutionary in the history of painting. One of Leonardo’s contemporaries wrote that he “painted Ginevra d’Amerigo Benci with such perfection that it seemed to be not a portrait but Ginevra herself.” Its lifelike and forthright portrayal broke with conventions of earlier Renaissance portraiture of women, including a preference for the more detached profile view. Ginevra de’Benci is one of the first known three-quarter view portraits in Italian art. She eyes the viewer directly. The planes of her face subtly modeled, she may have “come to life” before viewers in a fashion more vivid than any other painting they had seen before.