The Ugly Duchess: A painting centuries ahead of its time

A Grotesque Old Woman, by Flemish artist Quinten Massys, is one of London’s National Gallery’s most intriguing paintings. The ugly, sallow, and wrinkled woman, often referred to as ‘The Ugly Duchess’, not only employed genderplay and humour that was years ahead of its time but served as inspiration for Sir John Tenniel’s drawing of the infamous duchess in Alice’s Adventures in Wonderland.

The painting shows a disguised woman adorned in aristocratic regalia. She wears the escoffion, a horned headdress, which is not only a comment on the vanity of the erudite, as the headdress was far out of fashion by 1513 when it was painted, but the iconic headwear is also seen in Tenniel’s work illustrating the Duchess in Lewis Carroll’s book.

The woman is also seen clutching a red flower, symbolising her want to attract a suitor, but the bud is one that can never blossom. In a lot of ways, she is condemned by her own delusions – that she is a beautiful, sought-after aristocrat.

The extent of her ugliness led the art world to believe she was indeed a female, but one suffering from a disease affecting the bone structure. Medical experts have often weighed in to theorise the specific disease, which was narrowed down to Paget’s, an illness that inflames and deforms the bones of the face. It’s reasonably credible, given the elongated skull and droop of her skin.

However, recently, it has come to light that the Ugly Duchess was likely a Duke. Emma Capron, a leading Renaissance art expert, told The Guardian that “she is most likely a he”, dismissing the claims of Paget’s disease that led critics to think The Duchess was a woman, saying: “It’s not Paget’s, nor any of the other suggestions like dwarfism or elephantiasis. I’m really reluctant, too, to have doctors going around galleries and giving diagnoses.”

Capron continued to elaborate that “[The painting shows] a cross-dresser as a play on gender. Massys was very interested in carnivals where men would impersonate women, which could explain his interest in toying with gender”.

Naturally, people would point to the striking cleavage as evidence of otherwise, but as Capron reasons, “the breasts, with their brazen and scandalous cleavage, are a Massys fantasy”. The play on gender was said to be inspired by an Erasmus essay, ‘In Praise of Folly’, a critique of women’s vanity, specifically targeting those who “still play the coquette”. We see this play out in the painting with the withered rose and headgear worn by far younger women.

As well as the confusion surrounding its gender, the painting was often wrongly attributed as a lost work of Leonardo da Vinci because the cartoonish play with facial forms was strikingly similar to the Italian artist. But it’s now widely agreed upon that da Vinci’s caricatures were, in fact, based on Massy’s drawing, which he often traded with his fellow artists.