An old aristocrat or a man in a bonnet? Who was the duchess in the ugliest painting in art history?

For a work of art that evokes so many emotions, little is actually known about "The Ugly Duchess." More information can be gleaned from the text than from confirmed historical facts. Perhaps that's why the Antwerp painter's work remains so intriguing. Art curators estimate that the oil-on-panel painting was likely created around 1513, in a typical Renaissance style.

The painting, which is essentially a portrait, depicts an elderly woman. Her face is clearly deformed, with an oversized jaw, a wide nose, wrinkled skin, and exaggerated features. Despite her grotesque appearance, the woman adopts a flirtatious pose, attempting to expose her breasts and appear younger than her actual age.

In addition to the image of the aged figure itself , Massys also focused on details that make it much easier to understand the context of the entire work.

Both the attire and the accompanying elements of the figure classify her as a high-ranking aristocrat, even a duchess. The painting is most likely a satirical take on the female portrait , critiquing vanity, excessive focus on appearance, and age-inappropriate coquetry.

Massys, with the mastery of detail typical of Dutch painters, conveyed not only the physicality but also the moral assessment of the figures. What was the painter really trying to say with this painting?

The Ugly Duchess Quentin Massys 1513 / National Gallery, London / VCG Wilson/Corbis / Getty Images

Was the "Ugly Duchess" a man?

Some experts claim the painting depicts a man, but this is a rather bold theory, stemming from Massys's satirical approach to creating his works. This is the thesis put forward by Emma Capron, curator of the exhibition "The Ugly Duchess: Beauty and Satire in the Renaissance," which opens in March 2023 at the National Gallery in London.

Capron based her assumptions on Renaissance carnivals, during which men dressed up as women, among other things. Considering Massys's caricaturistic approach to creating his works, this may actually be a completely fictional character, exposing the Renaissance grotesque.

Is this the ugliest duchess in art history?

Over the centuries, various speculations have arisen regarding the identity of the figure depicted in the painting. One popular hypothesis, from 1693, posits that it is Margaret Maultasch, or Margaret, Duchess of Carinthia and Countess of Tyrol in the 14th century , known by the nickname "Maultasch" —which translates as "ugly face." However, this theory is questionable, as Margaret lived over 150 years before the painting was created, and her likeness is not recorded anywhere, making this identification symbolic rather than historical.

The Ugly Duchess Quentin Massys 1513 / National Gallery, London / VCG Wilson/Corbis / Getty Images

The "Ugly Duchess" and the Paget's Disease Theory

In 2008, Michael Baum, emeritus professor of surgery at University College London, offered a surprising theory about the figure in the painting. He believed the woman suffered from Paget's disease, a condition that leads to deformities of the facial bones. Why this suggestion? The protruding, oversized jaw, deformed nose, sunken cheeks, and visibly swollen, irregular lips may resemble symptoms of Paget's disease. The expert claims that the painting contains surprising details that may confirm that this type of disease may have been a form of inspiration for the painter.

"The Ugly Duchess" - or maybe it's a painterly essay?

Some also argue that Massys may have been inspired to create this work by Erasmus of Rotterdam's essay "In Praise of Folly" (1509), in which the author mercilessly mocks women who try to cling to their youth at all costs. Erasmus describes them as "constantly flirtatious," "unable to tear their eyes from the mirror," and "not ashamed to expose their flabby breasts." Very literal passages from this essay can be read in the painting.

That a Renaissance essay may indeed have influenced the painting is evidenced by the details the painter meticulously considered. The figure is dressed in an elegant but clearly unfashionable Burgundian costume, typical of the second half of the 15th century, resembling an outfit from the woman's youth.

Particularly striking is the distinctive saddle cap (escoffion) – once a symbol of aristocratic chic, it was already outdated by 1513, the time the painting was painted, and evoked more laughter than admiration. The cap may have been inspired by a 1410 portrait of the Burgundian princess Margaret of Bavaria, while the dress may have been taken from a 1475 portrait of Princess Margaret of York.

The Ugly Duchess Quentin Massys 1513 / National Gallery, London / VCG Wilson/Corbis / Getty Images

The red rosebud she holds in her hand also carries symbolic meaning. Typically interpreted as a sign of love or courtship, here it seems a frustrating substitute for affection, a harbinger of hope "that is unlikely to blossom." The entire portrait thus becomes not only a mockery of superficial vanity but also a bitter reflection on the passage of time and loneliness.

The painting "The Ugly Duchess" was originally part of a diptych, the other wing of which was a portrait of an elderly man. Today, the original image of the man is in a private collection, although its studio version is kept at the Musée Jacquemart-André in Paris.

Both the duchess and the man rest their left hands on the marble windowsill, giving the impression that they are extending beyond the frame of the painting, as if approaching the viewer. This illusionistic device not only gives the composition three-dimensional depth but also heightens the theatrical nature of the encounter between the two figures. Perhaps the point here isn't entirely about a romantic relationship, but rather a satirical one.

As has already been established, the pair of paintings were designed to complement each other. It is known that as early as 1645, they formed an inseparable whole, when the renowned printmaker Wenceslaus Hollar created a joint engraving of them, depicting a woman and a man facing each other in a single space. The portrait of the man itself was rediscovered only just before 1954 on the Paris art market, and to this day, it is unknown when and under what circumstances the diptych was separated. Hypotheses suggest that the relationship between the figures may allude to the medieval French allegorical poem "The Tale of the Rose."

In fact, no one knows when, where, or under what circumstances the work was created. The first documentation concerning it comes from France, in 1810. The work was purchased at a Paris auction by an English art dealer, and from then on, its fate has been linked to Great Britain.

In the 20th century, the painting belonged to the Blaker family, who attempted to donate it to the National Gallery in London on at least two occasions. One of its members, Hugh Blaker, once called it "the ugliest portrait in the world." Although he considered selling it, the sale never materialized.

Eventually, his heir, Jenny Blaker, decided to donate the painting to the National Gallery collection, where it has been since 1947.

For many years, it was believed that the painting might be a copy or pictorial interpretation of a lost drawing by Leonardo da Vinci. This belief was based on its resemblance to the characteristic caricatured heads often attributed to Leonardo. His sketches of grotesque figures with deformed faces and exaggerated facial expressions were very popular with artists and collectors, and it was believed that Massys may have been inspired by them.

However, contemporary research and chronological analysis of works increasingly point to the opposite direction of influence. Currently, Massys is considered a pioneer of this convention, and his original grotesque sketches and portraits may have been known in Italy and influenced Leonardo's circle of students. Therefore, rather than copying the Italian master, Massys himself may have been one of the first artists to embrace ugliness as a distinct artistic subject.

The character from Massys's painting became a direct inspiration for John Tenniel's illustrations for Lewis Carroll's classic novel "Alice's Adventures in Wonderland" (1865). The eccentric duchess, one of the book's most memorable characters, bears distinct features of Massys's original.

Particularly distinctive is her grotesque saddle cap, which was almost literally transferred to paper. Although Tenniel somewhat softened his heroine's beauty, he retained her caricatural facial expressions and theatrical mimicry, creating a character simultaneously comic and disturbing. In this way, the painterly grotesque of the early 16th century entered the world of children's literature, gaining new, cultural life in one of the most famous books of all time.