The Ugly Duchess is an oil on oak panel painting by Quentin Massys, created circa 1513. The work is widely regarded as a satirical portrait, probably intended to lampoon older individuals who behave as if they are still young. It is thought to represent a fictional, folkloric character from the world of carnival rather than a real person.

This painting was made as a pendant to Portrait of an old man, also by Quentin Massys. The composition features an elderly woman, depicted in half-length against a plain green background. She wears an elaborate headdress decorated with a geometric pattern and a large brooch, and her dress is cut low to expose her chest, a detail that contributes to the satirical intent. Her exaggerated facial features and the incongruity of her youthful attire with her aged appearance are rendered with meticulous detail, using fine brushwork and a clear, even light.

The figure holds a small flower in her right hand, which may further allude to themes of vanity or misplaced courtship. The painting is held in the collection of the National Gallery, London. It has long been recognized as a significant example of early sixteenth-century Northern European portraiture and satire. The work’s pendant, Portrait of an old man, was intended to complement this composition.

Over the centuries, The Ugly Duchess has attracted attention for its striking imagery and has been widely exhibited and reproduced as an example of Renaissance caricature.