I find Leonardo's grotesque drawings very interesting, as, even though they are weird and distorted, they somehow look as though they could exist. Most of them were not drawn from observation but from imagination, and Leonardo used the same sort of precise principles in their design - such as dividing the head into lines of latitude for the brow, the nose and the lip - that he was applying to his (far more numerous) drawings of beautiful and youthful faces.
This drawing, attributed to Francesco Melzi, is a faithful copy of a lost original by Leonardo (c. 1490). It shows a rather ugly old woman in a somewhat unflattering costume. Her weird, distinct headdress emphasises her oddly-shaped head and sticky out ears, and her revealing costume displays bits of her we would probably rather not see.
A surviving, but unfortunately trimmed, drawing by Leonardo himself, from the same year, seems to have been a preparatory sketch for his ugly old woman. Many of his facial studies, both beautiful and grotesque, were done in profile, Leonardo believing such an angle to be the best way to show the features of the face.
Leonardo's old woman is not grotesque simply because she is old; it is the woman's vanity and ostentatiousness, reflected in her costume and bearing, that make her ugly. An extract from Erasmus' Praise of Folly (1511) is included in Leonardo da Vinci: The Divine and the Grotesque to suggest a similar message to that illustrated in the drawing:
It is even more amusing to see these old women, so ancient they might as well be dead... They pay a good price for the services of some handsome young Adonis. They never cease smearing their faces with make-up. They can't tear themselves away from the mirror... They show off their withered and flabby breasts... Everyone laughs at these things as utterly foolish (and indeed they are), but the old bags themselves are perfectly self-satisfied.
Quinten Massys of Antwerp may have seen several of Leonardo's grotesque faces, as he used similar designs in a few of his paintings. One of the gypsy faces in the sketch at the top of this post appears in his Grotesque Betrothal and, famously, he painted his own Grotesque Old Woman (c. 1520), which can be seen in the National Gallery in London:
This is certainly one of my favourite paintings in the National Gallery, because it's one of the few paintings that actually puts a smile on people's faces - the laughter is a welcome change from the respectful, decorous hush generally found in museums and galleries. There's also something inherently charming about the old woman's naive ignorance of her own ugliness. The dreamy eyes and coy mouth rally add to the humour.
While Erasmus accuses vain old ladies of having their eyes on 'some handsome young Adonis', Massys depicted his grotesque old woman as seeking the affections of a man of a similar age, who rejects her offer of a rosebud. The idea may also have been inspired by Leonardo, who drew a Satire on Aged Lovers (c. 1490, above); however, Leonardo's old man is much more keen on his admirer than Massys' is.
Massys' narrative was later depicted in an etching (above) by Wenceslaus Hollar around 1645, under the title The King and Queen of Tunis, with the old man (not exactly in a position to be fussy, it must be said) rejecting his admirer's advances. The painting of the old woman still works on its own, however; the rosebud she is holding, along with her wistful gaze into (apparently) nothing could be seen to allude to a youth long since lost.
Sir John Tenniel is more likely to have used Massys' old woman as a source for his Ugly Duchess in Alice in Wonderland, because the Leonardo version's headdress does not feature the embroidered pattern seen in the Tenniel illustrations, and the Hollar version does not give the headdress such a distinct shape. The Punch cartoonist could have seen it in the collection of Alfred Seymour; alternatively he may have used an engraving (above) of the painting by Gilles-Antoine Demarteau.
But there may have been other sources as well. Tenniel had depicted medieval women with similarly shaped headdresses in several of his Punch cartoons (above), and these women have completely different faces. Furthermore, Tenniel's Duchess' face doesn't really resemble that of Massys'.
After Gordon Brown, who wasn't around in Lewis Carrol's day, the closest facial resemblance to the Tenniel Duchess can be found in an engraving (above) by F. W. Fairholt for Thomas Wright's History of Caricature and Grotesque in Literature and Art(1865). The illustration is of a misericord, which often featured grotesque faces. The thuggish face shown quite closely resembles Tenniel's Duchess. It is likely Tenniel had come across the book in his earlier days.
This perhaps accounts for the Duchess having a big bulky chin, in contrast to the 'sharp little chin' described by Lewis Carrol. Nevertheless the Tenniel Duchess' chin does at least end in a point, the better to dig into Alice during a conversation. The Tenniel Duchess and her distinctive headdress have been an influence on many of the Alice illustrators, including Gwyneddm Hudson: