Read my earlier posts on the Duchess here and here.
This photo appears as a frontispiece to a book of the Wife of Bath's tale (from Chaucer's Canterbury Tales). The miserichord (referred to as 'The Shrew' in the caption) seems to be the source for F. W. Fairholt's engraving for History of Caricature and Grotesque in Literature and Art (1865), which was probably seen by John Tenniel and used as inspiration for his Duchess in Alice's Adventures in Wonderland.
There is no reason to believe, however, that he ever saw the actual miserichord itself, which can be found in the church of St. Lawrence in Ludlow; Tenniel's Duchess bears a closer resemblance to the engraving than to the original. It is likely that the miserichord was added to the church in the 15th century, when most of the structure was rebuilt.
A character with a similar headdress can be seen in an illustration for Les Echecs Amoureux (c. 1496-8) depicting Pluto and his wife Persephone, who are unusually depicted as aged and ugly. Even though this dates from before Massys' Grotesque Old Woman (c. 1513), it need not be considered a source for the painting, so much as suggesting that this kind of headdress was probably a sort of accepted shorthand in art at the time for an ugly old woman. The shape of the headdress gives the head an overall deformed look (though in this particular illustration it perhaps has a double meaning, alluding to the horned minions on the right hand side of the composition).