English: Anne of Cleves (1515–57), a daughter of John III, Duke of Cleves, was the fourth wife of Henry VIII. Holbein was sent to paint her at Düren in summer 1539, so that Henry could appraise her as a possible wife. Holbein posed Anne square-on and in elaborate finery. Henry was disappointed with her in the flesh, and he divorced her after a brief, unconsummated marriage. He redesignated Anne as "king's sister", and she remained in England, where she died during the reign of Queen Mary.

The use of parchment suggests that Holbein painted, or at least began, the portrait in Düren. A miniature version in the Victoria and Albert Museum was probably painted at the same time. Holbein also produced a portrait of Anne's sister, Amelia, which is now lost. Nicholas Wotton, the head of the English delegation, reported to Henry: "Your Grace's servant Hanze Albein hathe taken th'effigies of my lady Anne and the lady Amelye and hath expressed theyr images very lyvely". The tradition that Holbein flattered Anne is not borne out by the evidence: no one except Henry ever described her as repugnant.

References:

• Bätschmann, Oskar, & Pascal Griener, Hans Holbein, London: Reaktion Books, 1997, ISBN 1861890400, p. 192.
• Ganz Paul, The Paintings of Hans Holbein: First Complete Edition, London: Phaidon, 1956, p. 259.
• Rowlands, John, Holbein: The Paintings of Hans Holbein the Younger, Boston: David R. Godine, 1985, ISBN 0879235780, p. 151.
• Strong, Roy, Artists of the Tudor Court: The Portrait Miniature Rediscovered, 1520–1620, ISBN 0905209346, p. 48.
• Wilson, Derek, Hans Holbein: Portrait of an Unknown Man, London: Pimlico, 2006, ISBN 1844139182, p. 260.