Painted probably in the late 1470s, Ginevra de' Benci is the earliest portrait firmly attributed to Leonardo's own hand^[1]. Before around 1440, Florentine panel portraits of individuals were almost entirely of men; women then began to appear, but nearly always in strict profile, eyes averted^[1]. That format read as chaste and decorous: a woman's face was available to be looked at, but she could not look back^[1]. Men, by contrast, had begun to be shown in three-quarter view and direct engagement with the viewer by around 1450^[1]. Leonardo gave Ginevra that same treatment, turning her toward the viewer and letting her eyes meet ours, a pose more usual in fifteenth-century Netherlandish portraits than in Italian ones^[1]. In Florence the choice was startling. It helped displace the profile portrait as the standard format for women, and its influence shows up soon afterward in a slightly later portrait by Lorenzo di Credi, now in the Metropolitan Museum, which some historians think may depict the same sitter^[1].

The back of the panel, as much a part of the picture as the front, carries a painted emblem: a wreath of laurel and palm encircling a sprig of juniper, joined by a scroll reading, in Latin, 'she adorns her virtue with beauty'^[2]. Ginevra's name plays on the Italian word for juniper, ginepro, and Leonardo set a real juniper bush behind her head on the front of the panel as the same pun in a different register^[2]. Historians have also linked the emblem to Bernardo Bembo, the Venetian ambassador to Florence in the later 1470s, whose own personal device was a near-identical wreath of laurel and palm^[1]. Bembo commissioned ten poems addressed to Ginevra from writers close to the Medici circle, evidence of a courtly, largely literary infatuation^[1]. Whether Bembo also commissioned the portrait itself remains disputed among historians rather than settled fact, and the picture's date has been argued anywhere from the mid-1470s to 1480 partly on the strength of that question^[1].

Ginevra was born in 1457 into the Benci, a wealthy and culturally connected Florentine family; her grandfather managed the Medici bank, and her father was a patron and friend of the philosopher Marsilio Ficino^[1]. In 1474 she married Luigi Niccolini, a Florentine city official less prominent than her own relations; the marriage did not go smoothly financially, and by his death in 1505 his heirs could not repay her dowry^[1]. Ginevra herself was recognised in her own lifetime as a poet, praised in verse by contemporaries including Lorenzo de' Medici, though only one line of her own writing survives: 'I ask your forgiveness, and I am a mountain tiger'^[1]. That fragment, stripped of its original context, still suggests a more forceful character than the reserved, composed face Leonardo painted^[1].