Old Master Paintings

Botticelli: Master of Florentine Portraiture

By Elizabeth Pilliod

F aces. Likenesses. Facsimiles. Portraits. For contemporary viewers, the notion of taking a picture of oneself or another person, snapping a selfie, or uploading a personal video is predicated on the principle of instantaneity (and fraught only with issues of violations of privacy or desires for a career as an influencer). How far we have come from the traditions of the ancient Romans, whose endeavors to capture likenesses were intended to span all time! To preserve the memory of their ancestors they had wax masks made of the dead that they could carry in funerals so their entire family—the living and the dead—could participate. Collected and stored in cupboards the wax imagines became the basis for marble heads, prominently displayed in patrician Roman houses in the atria, the space through which all visitors and business traffic passed. This kind of advertisement of social prominence, ancient lineage, and familial continuity was revived in Renaissance Europe, reconstituted from fragments of sculpture and texts such as Pliny’s Natural History.1 In Florence in particular, this preservation and celebration of family members melded perfectly with the Florentine notion of family, as a group of kinsmen descended from a common ancestor.2 By the late 1430s the architect and humanist Leon Battista Alberti would pen a treatise on the family (Della famiglia) and in his manual on painting (De Pictura) he would claim that one of the divine properties of painting was the ability of portraiture to make “the dead seem almost alive.”3 Another characteristic of the Florentines was their champion record-keeping. Just as every aspect of their businesses was written down in ledgers, heads of households recorded important life events into diaries or ricordi. The recording of faces was pursued with the same assiduity. For the privileged this meant embedding portraits in the altarpieces and frescoes that covered the spaces in their family chapels. Sometimes the faces of contemporary Florentines mingled with the spectators in religious dramas (see the essay in this volume by Bruce Edelstein on portraits in Botticelli’s Del Lama Adoration). In other cases, in the depiction of signal events, portraits of recognizable contemporaries appealed to viewers’ sense of inclusion and fiorentinità (“Florentine-ness”). An early, renowned example was at the church of the Carmine where the remarkable painter Masaccio (1401-1428) included portraits of Florentines in a fresco of the public procession that accompanied the 1422 dedication of the very church in which they were painted.4 By the time Sandro Botticelli was engaged in painting altarpieces, mythologies and portraits for the Medici, many Florentine families had already begun collecting portraits of their ancestors and famous personages, both historical and contemporary.5

These aspects and developments in portrait painting in the fifteenth century are crucial to a full understanding of the brilliance of Botticelli’s Portrait of a Young Man Holding a Roundel. It would be useful to consider the background and context of the type of portrait he painted. The making of portraits was triggered by events ranging from impending weddings, deaths, the imminent transfer of a family member to a far-off location, and the desire to have collections of famous people as exempla, among other impulses. By the mid-fifteenth century the production of images of single individuals, free-standing portraits on wood panels, started to skyrocket, if one can judge by the number of surviving portraits. Another change was while the early fifteenth-century portraits had been strictly in profile, now male sitters started to turn towards the viewer, showing more of their faces. These developments have been traced to the influence of the new cult of personality and Humanism; the arrival of icons after the fall of Constantinople; the accessibility of Northern portrait paintings via the global trade that united Italy with the rest of Europe; and the need for images to trigger remembrance so that prayers would be said for the soul of the deceased, among other sources.6

Fig. 1. Andrea del Castagno, Portrait of a Man, 1450-57, National Gallery of Art, Washington, D.C., The Andrew J. Mellon Collection (1937.1.17)

One of the first Florentine three-quarter or seven-eighths views7 is of an imposing man who remains unidentified (fig. 1).8 The painting likely reflects the sculptural models emanating from Donatello and his contemporaries. Attributed to Andrea del Castagno (1423-1457), the man wears a red cloak over a black doublet and white shirt. The high cylindrical neck of the black doublet he wears is identical to that worn by the young man in Botticelli’s Portrait of a Young Man Holding a Roundel. The length of the figure, cut off just above the waist, as well as the voluminous cloak and the way he grasps a portion of it with his right hand recalls Roman funerary reliefs and urns which were readily visible in the fifteenth century.9 His gesture thus relates him to antique models, which for a Florentine reflected their pride in being a city founded by the Romans. The expensive red color of the cloak marks it as a valuable item and its wearer as a person of means. However, unlike the Roman prototypes it recalls, Castagno has ruptured the simple planarity of their poses; instead the sitter is turned aslant, one shoulder receding into the background. It is this innovation that marks a turn in Florentine portraiture that will lead to Botticelli. As he turns with stately dignity, his eyes moving ahead of his torso, the image seems to project an identity based on competence, resolve, and an air of superiority. The strongly outlined facial features and fingers slightly stand out from the man’s body—a common difficulty in integrating these parts with the overall body structure in early portraits.

Fig. 2. Piero del Pollaiuolo, Portrait of Galeazzo Maria Sforza, 1471, Uffizi Gallery, Florence Bridgeman Images

A similar pose, although now exaggerated, is found in Piero del Pollaiuolo’s Portrait of Galeazzo Maria Sforza (fig. 2). Painted during Sforza’s stay in Florence in 1471, the portrait shows the duke sporting the blue veste dotted with golden lilies that he was recorded as wearing as he entered Florence with his entourage. The lilies attested to his union with the French house by virtue of his marriage. His visit acknowledged the political relationship he had forged with Florence, and as this portrait was in the collection of Lorenzo the Magnificent, it is likely that Lorenzo himself commissioned the image to commemorate his alliance with Sforza.10 Instead of engaging the viewer, Sforza leans back, gesturing emphatically, perhaps underscoring an important point with his index finger. His body is more rotund than that of the Man painted by Castagno, but the same model, the Roman funerary bust, informs the work as an extended finger is a common type among them.11 The association with the antique past again underlies a sense of historical continuity and destiny: Milan was the capital of the Western Roman Empire. As a portrait of a duke advertising his connection to French royalty and wearing a costume of Franco-Burgundian court design, the image exemplifies the international sweep of Lorenzo the Magnificent’s connections, and by having the image in his collection with portraits of other leaders, Lorenzo laid claim to membership in that illustrious group himself.

Fig. 3. Biagio d’Antonio, Portrait of a Boy, 1476-80, National Gallery of Art, Washington, D.C., Samuel H. Kress Collection (1939.1.179)

More typical are portraits whose sitters’ identities remain unknown. An unidentified young man, the Portrait of a Boy of circa 1476-80 by Biagio d’Antonio (1446-1516), is deceptively simple (fig. 3). Biagio himself, although mostly overlooked today, enjoyed a successful career as a painter in Florence and was among those called to Rome by Pope Sixtus IV to paint the lives of Christ and Moses along the upper border of the walls of the new Sistine Chapel.12 The sitter, again in the same slightly oblique pose, although not displaying his hands, supplies another aspect of portraiture in the age of Botticelli. Given his youth, the sitter is unlikely to have acquired high position or performed noteworthy deeds, as the subjects of our two previous portraits had. He gazes directly at the viewer. The boy’s head is framed by two wispy clouds and backed by a brilliant sky. He may be beyond this life, a portrait made to preserve the likeness of a lost child. Artists are documented as creating such images, from drawings, death masks, or, given the idealization of the face of this youth, simply by painting an ideal young man to stand for the memory of the lost one.13 Behind him is an intriguing landscape, with trees painted as if their leaves were mounted on pinwheels and what appear to be glacial peaks, perhaps a fantastical image intended to evoke alpine regions.14 The unusual landscape may point to a real place beyond the Alps. Many Florentines had businesses and second homes in northern cities, for instance in Nuremberg and Bruges. It is known that sons were customarily sent off to take over or learn the ropes at these far-off locales. Sometimes they never returned. A portrait such as this one could have been made to keep the memory alive of a boy scheduled for an imminent departure. The very inclusion of the landscape, derived from Northern portraits themselves, indeed may support this possibility.

Fig. 4. Hans Memling, Portrait of a Man holding holding a Sestertius of Nero, ca, 1475, Koninklijk Museum voor Schone Kunsten, Antwerp (inv. 5 DD.42) Hans Memling/Koninklijk Museum voor Schone Ku

Not only did Florentines travel to and live in Northern areas where they encountered works of art with new qualities, but they also brought paintings, sculptures, medals, and other objects back to Florence, the most famous example of which is Hugo van der Goes’ Portinari Altarpiece imported by Tommaso Portinari and installed in the church of S. Egidio at Florence, now in the Uffizi (inv. 1890, no. 3191-93). The figural poses, inclusion of landscape backgrounds, and emblematic items in Northern portraits have been shown to directly influence the evolution of portraiture in Italy.15 In Biagio d’Antonio’s Portrait of a Boy, features such as the silhouetting of the figure against a radiant sky dotted with evanescent clouds and the mysterious structures near the enigmatic mountain peaks were exactly such features. In some cases, the direct influence of a northern painting on a Florentine one can be proven. One such example is the Portrait of a Man holding a Sestertius of Nero, c. 1475 (fig. 4). It was painted by Hans Memling (c. 1430-1494), an artist who is known to have had Italian patrons, including the Portinari family in Florence.16 In fact, a portrait by Hans Memling of Tommaso Portinari’s nephew, Benedetto Portinari, is also in the Uffizi.17 As some scholars have pointed out, the sitter in Memling’s Antwerp portrait is likely a Florentine, given the reference to southern vegetation in the palm tree in the right background. More importantly, it is certain that Memling’s painting was in Florence in the late-fifteenth century as some of its details were accurately copied by Florentine painters.18 Once its presence is confirmed in Florence the significance of its influence on Botticelli can be understood. In fact, it provides an example for the key action of Botticelli’s Portrait of a Young Man Holding a Roundel: the man in Memling’s portrait displays a collectible, a coin, as an object of significance to those looking at the picture.19 He is perhaps a collector of such antiquities, or there is some quality or connotation in the coin that is of importance to him.20

While the Memling therefore undoubtedly provided the prototype for Botticelli’s Portrait of a Young Man Holding a Roundel, the alterations Botticelli has made to his model are masterful. First, he has corrected the cramped and uncomfortable proportions of the head, body, and hands of the sitter. In Botticelli’s remaking of the design the hands are neither disembodied nor too small. The head does not loom too large as it does in the Memling. In fact, the correct proportions that had always disturbed artists—the problem that one’s hand could be even larger than one’s face—is realistically drawn.21 The youth’s hands are large and properly sized, but precisely because they are gracefully collapsed into folds as they brace and cradle the roundel, they are simultaneously correctly large but very discrete. Every joint and bend is meticulously described. One feels the tension in his fingers, the careful balancing act they are performing. All of this is because the roundel is intensely important.

Fig. 5. Andrea del Verrocchio, Lady with Flowers, ca. 1475-80, Museo Nazionale del Bargello, Florence (inv. 115 S)
Left align with paragraph starting below Bridgeman Images

Botticelli’s attention to the important role that the hands play in this image is indebted to arguably the most influential artist of the 1470s and 1480s in Florence, Andrea del Verrocchio (1435-1488). It was Verrocchio who extended the body to create a full half-length figure. His solution allowed the viewer to see the motivation for the facial expressions and movements of the hands that until then had simply been cobbled together. His statement of this is found in his half-length Lady with Flowers, c. 1475-80 (fig. 5). In it, a sense of the more subtle emotions and whims of the individual are revealed.22 The immediacy of the subject and potential for interaction between subject and viewer influenced artists from Botticelli to Leonardo.

Rather than use the northern-style background landscape of Memling’s or Biagio d’Antonio’s portraits, Botticelli instead indicates only an idealized space: a celestial blue, cloudless, almost lapidary background, to perfectly complement the auburn hair and apricot-tinged flesh of the youth. Unlike the flat background in Pollaiuolo’s portrait of Galeazzo Sforza or the generic sky behind Castagno’s subject, there is an insistently structural component to the portrait. The window framed in pietra serena (the dove-grey sandstone used by Florentine architects to trim and emphasize structural details from Brunelleschi to Michelangelo) behind him and the stone wall in the foreground demarcate a narrow band of space in which the figure acts. It seems less a real space than an ideal construction into which the young man is inserted. He is ensconced in an airless, atmosphere-less zone. Nonetheless, his presence there is powerful. He seems magnified, almost monumental, and virtually about to come into physical contact with the viewer.

The crystalline appearance of the walls, window, and blue sky, all wiped perfectly clean, lend an otherworldly quality to the image. A hush, a perfect silence pervades the whole, placing the viewer in a psychologically unusual position. It is a picture that asks questions of the viewer, is an intellectual challenge, and is of a mysterious but undeniable beauty. A masterpiece of portraiture that perfectly encapsulates and surpasses everything before it.


1. In lamenting the decaying of these traditions, Pliny the Elder describes them in detail, in his Natural History XXXV, 2-4.

2. F.W. Kent, Household and Lineage in Renaissance Florence: The Family Life of the Capponi, Ginori, and Rucellai, Princeton 1977, remains unsurpassed in its treatment of every aspect of the subject.

3. Leon Battista Alberti, On Painting, J. Spencer (trans.), rev. ed., New Haven and London 1966, p. 63: “Painting contains a divine force which not only makes absent men present, as friendship is said to do, but moreover makes the dead seem alive,” an adaptation of a line in Cicero’s De Amicitia, VII, 23. And, ibid., “Thus the face of a man who is already dead certainly lives a long life through painting.”

4. G. Vasari, Le vite de’ più eccellenti pittori, scultori ed architettori, G. Milanesi (ed.), vol. 2, Florence 1906, p. 295: “Accade, mentre che e’lavorava in quest’opera, che e’fu consagrata la detta chiesa del Carmine; e Masaccio, in memoria di ciò, di terra verde dipinse di chiaro scuro, sopra la porta che va in convento dentro nel chiostro, tutta la sagra come ella fu; e vi ritrasse infinito numero di cittadini in mantello ed in cappuccino, che vanno dietro alla processione….” Attendance was a demonstration of both civic responsibility and prominence.

5. For the Medici, see J. Shearman, “The Collections of the Younger Branch of the Medici,” in Burlington Magazine, 117 (1975), pp. 12-27; and K. Langedijk, The Portraits of the Medici: 15th-18th centuries, vol. 1, Florence 1981, pp. 13-38.

6. The history of portraits of women is another matter. The immense bibliography on portraiture is too voluminous to list, but for some references to these specific issues see: On the first, J. Pope-Hennessey, The Portrait in the Renaissance, Bollingen Ser. XXXV, 12, Princeton 1966, chapters 1-2; On the change to full-face, L. Campbell, The Renaissance Portrait: European Portrait Painting in 14th, 15th and 16th centuries, New Haven and London 1990, pp. 75-86; On the influence of sculpture, A. Wright, “Memory of Faces,” in Art, Memory and Family in Renaissance Florence, G. Ciappelli and P.L. Rubin (eds.), Cambridge 2000, pp. 98-102; On Byzantine icons: see Alexander Nagel’s essay in the present publication; and on souls see L. Syson, “Witnessing Faces, Remembering Souls,” in El retrato del Renacimiento, M. Falomir (ed.), Madrid 2008, pp. 416-20.

7. Lorne Campbell has underscored the need to recognize this pose as a “seven-eighths view.” See L. Campbell, in Memling's portraits, exhibition catalogue, T.-H. Borchert (ed.), Ghent 2005, p. 56.

8. K. Christiansen, in The Renaissance Portrait from Donatello to Bellini, exhibition catalogue, K. Christiansen and S. Weppelmann (eds.), New Haven and London 2011, pp. 123-4, cat. no. 21.

9. I. Lavin, “On the Sources and Meaning of the Renaissance Portrait Bust,” in Art Quarterly, no. 33 (1970), pp. 207-15; reprinted in: The Art of Commemoration in the Renaissance: The Slade Lectures, M. Aronberg Lavin (ed.), New York 2020, pp. 23-50.

10. A. Bayer, in The Renaissance Portrait from Donatello to Bellini, exhibition catalogue, New York 2011, pp. 169-71, cat. no. 48.

11. See some examples in D.E.E. Kleiner, “Roman Group Portraiture: The Funerary Reliefs of the Late Republic and Early Empire,” Ph.D diss., Columbia University 1975, New York 1977, figs. 30, 50c,75b and d.

12. See E. Fahy, in The Renaissance Portrait from Donatello to Bellini 2011, pp. 132-34, cat. no. 26, for a discussion of the three known portraits by Biagio.

13. Although it is more usual to identify portraits derived from death masks based on clues such as closed or downcast eyes (see for example, Botticelli’s Portrait of Giuliano de’ Medici), cases are also known in which the artist, while working from a death mask, instead reanimates the lost sitter.

14. The glacial blue peaks may call to mind the stalactites dissolving in the mist in the far background of Leonardo’s Paris Virgin of the Rocks, begun for the Milanese confraternity of the Immaculate Conception when he first arrived in Milan in 1483. The pinwheel trees recall those in Leonardo’s first extant drawing, the 1473 Drawing of the Arno River Valley.

15. P. Nuttall, in Memling's portraits, T.-H. Borchert, (ed.), exhibition catalogue, Ghent 2005, pp. 75-85.

16. This fascinating portrait has been much discussed. See K.B. McFarlane, Hans Memling, Oxford 1971, pp. 14-15, who pointed out the possible naming-reference in the coin; and ibid, pp. 34-35 for his Italian patrons, including the Portinari. For the sitter as likely Italian and this specific portrait related to a portrait of a man in the Uffizi, see D. de Vos, Hans Memling: five centuries of fact and fiction: Catalogue, exhibition catalogue, Ghent 1994, pp. 94-95, cat. no. 19. For the suggestion that it depicts Bernardo Bembo and should be dated 1473-74, see T.-H. Borchert in Memling’s portraits 2005, p. 160, cat. no. 10. For the dating ca. 1475 see L. Campbell in El retrato del Renacimiento 2008, pp. 466-67, cat. no. 17.

17. Inv. No. 1090. K.B. McFarlane 1971, p. 34-35, and note 30.

18. P. Nuttall in Memling’s Portraits 2005, pp. 78-80, outlines how, if the sitter is indeed Bernardo Bembo, the Venetian ambassador to Florence, he could have brought it with him to Florence after his service in the north, where Memling would have painted it.

19. R. Lightbown’s claim that the Memling was the inspiration for Botticelli’s Man with a Medal of Cosimo the Elder in Piero della Francesca, London 1992, p. 231, has been frequently repeated. In fact, the Memling is the inspiration for the Portrait of a young man holding a roundel. The way Memling has pressed the man’s fingers and coin into the corner and used them to construct a bridge between the space of the viewer and that of the sitter in the portrait is not a model for the Man Holding a Medal, as his hands are in a completely different position: flattened and held against his chest, they stand back from the frame of the image rather than coming out over it. The presence of a balustrade in the Memling is revealed by the two leaves that rest on it. The man’s hands therefore projected out and likely would have cast a shadow on the barrier—even if one were not actually painted, its existence is indelibly inscribed on the viewer’s mind.

20. No sane collector would exhibit a coin of a thoroughly debauched emperor as a symbol of his own character, so the meaning of this coin to the sitter remains undiscovered. The earlier suggestion that it could reflect his name, for example “Nerone”, or “Neri” had seemed likely, but see note 16 above.

21. For this comment on the theory of portrait making, see L. Campbell 1990, p. 96.

22. J. Pope-Hennessey 1966, pp. 82-84; A. Luchs and D. Smith, in Verrocchio: Sculptor and Painter of Renaissance Florence, exhibition catalogue, A. Butterfield (ed.), Princeton 2019, pp. 134-39, cat. no. 8. Verrocchio was also a painter and he is said to have painted a portrait of Lorenzo the Magnificent’s beloved Lucrezia Donati. It is likely to have also been a half-length with the mobility of her arms and hands used expressively.

Stay informed with Sotheby’s top stories, videos, events & news.

Receive the best from Sotheby’s delivered to your inbox.

By subscribing you are agreeing to Sotheby’s Privacy Policy. You can unsubscribe from Sotheby’s emails at any time by clicking the “Manage your Subscriptions” link in any of your emails.

More from Sotheby's