The artist Hans Holbein the Younger was dispatched to Düren to paint portraits of Anne and her younger sister, Amalia, each of whom Henry was considering as his fourth wife.
Henry required the artist to be as accurate as possible, not to flatter the sisters.
The portraits are now located in the Musée du Louvre in Paris and the Victoria and Albert Museum in London.
Another 1539 portrait, by the school of Barthel Bruyn the Elder, is in the collection of Trinity College, Cambridge.

Negotiations to arrange the marriage were in full swing by March 1539.
Cromwell oversaw the talks and a marriage treaty was signed on 4 October of that year.

Henry valued education and cultural sophistication in women, but Anne lacked these traits.
 She had received no formal education but was skilled in needlework and liked playing card games.
She could read and write, but only in German.
Nevertheless, Anne was considered gentle, virtuous and docile, which is why she was recommended as a suitable candidate for Henry.

Anne was described by French ambassador Charles de Marillac as tall and slim, "of middling beauty and of very assured and resolute countenance."
She was fair-haired and was said to have had a lovely face.
In the words of the chronicler Edward Hall, "Her hair hanging down, which was fair, yellow and long ... she was apparelled after the English fashion, with a French hood, which so set forth her beauty and good visage, that every creature rejoiced to behold her."
She appeared rather solemn by English standards, and looked old for her age.
Holbein painted her with a high forehead, heavy-lidded eyes and a pointed chin.

Henry met her privately on New Year's Day 1540 at Rochester Abbey in Rochester on her journey from Dover.
Henry and some of his courtiers, following a courtly-love tradition, went disguised into the room where Anne was staying.
Eustace Chapuys reported:
 Catherine of Aragon
 Anne Boleyn
 Jane Seymour
 Anne of Cleves
 Catherine Howard
 Catherine Parr
[The King] so went up into the chamber where the said Lady Anne was looking out of a window to see the bull-baiting which was going on in the courtyard, and suddenly he embraced and kissed her, and showed her a token which the king had sent her for New Year’s gift, and she being abashed and not knowing who it was thanked him, and so he spoke with her.
But she regarded him little, but always looked out the window….
and when the king saw that she took so little notice of his coming he went into another chamber and took off his cloak and came in again in a coat of purple velvet.
And when the lords and knights saw his grace they did him reverence.

According to the testimony of Henry's companions, he was disappointed with Anne, feeling that she was not as described.
According to the chronicler Charles Wriothesley, Anne "regarded him little", though it is unknown whether she knew this was the king.
Henry then revealed his true identity to Anne, although he is said to have been put off the marriage from then on.
Henry and Anne then met officially on 3 January on Blackheath outside the gates of Greenwich Park, where a grand reception was laid out.

Most historians believe that Henry's misgivings about the marriage were blamed on Anne's alleged unsatisfactory appearance and her failure to inspire him to consummate the marriage.
He felt that he had been misled after his advisors had praised Anne's beauty: "She is nothing so fair as she hath been reported", he complained.
Cromwell received some blame for the Holbein portrait, which Henry believed had not been an accurate representation of Anne, and for some of the exaggerated reports of her beauty.
When the king finally met Anne, he was reportedly shocked by her plain appearance, and the marriage was never consummated.

Henry urged Cromwell to find a legal way to avoid the marriage but, by this point, doing so was impossible without endangering the vital alliance with the Germans.
In his anger and frustration, the King turned on Cromwell, to his subsequent regret.
The artist Hans Holbein the Younger was dispatched to Düren to paint portraits of Anne and her younger sister, Amalia, each of whom Henry was considering as his fourth wife. Henry required the artist to be as accurate as possible, not to flatter the sisters. The portraits are now located in the Musée du Louvre in Paris and the Victoria and Albert Museum in London. Another 1539 portrait, by the school of Barthel Bruyn the Elder, is in the collection of Trinity College, Cambridge.
Negotiations to arrange the marriage were in full swing by March 1539. Cromwell oversaw the talks and a marriage treaty was signed on 4 October of that year.
Henry valued education and cultural sophistication in women, but Anne lacked these traits.  She had received no formal education but was skilled in needlework and liked playing card games. She could read and write, but only in German. Nevertheless, Anne was considered gentle, virtuous and docile, which is why she was recommended as a suitable candidate for Henry.
Anne was described by French ambassador Charles de Marillac as tall and slim, "of middling beauty and of very assured and resolute countenance." She was fair-haired and was said to have had a lovely face. In the words of the chronicler Edward Hall, "Her hair hanging down, which was fair, yellow and long ... she was apparelled after the English fashion, with a French hood, which so set forth her beauty and good visage, that every creature rejoiced to behold her." She appeared rather solemn by English standards, and looked old for her age. Holbein painted her with a high forehead, heavy-lidded eyes and a pointed chin.
Henry met her privately on New Year's Day 1540 at Rochester Abbey in Rochester on her journey from Dover. Henry and some of his courtiers, following a courtly-love tradition, went disguised into the room where Anne was staying. Eustace Chapuys reported:
 Catherine of Aragon
 Anne Boleyn
 Jane Seymour
 Anne of Cleves
 Catherine Howard
 Catherine Parr
[The King] so went up into the chamber where the said Lady Anne was looking out of a window to see the bull-baiting which was going on in the courtyard, and suddenly he embraced and kissed her, and showed her a token which the king had sent her for New Year’s gift, and she being abashed and not knowing who it was thanked him, and so he spoke with her. But she regarded him little, but always looked out the window…. and when the king saw that she took so little notice of his coming he went into another chamber and took off his cloak and came in again in a coat of purple velvet. And when the lords and knights saw his grace they did him reverence.
According to the testimony of Henry's companions, he was disappointed with Anne, feeling that she was not as described. According to the chronicler Charles Wriothesley, Anne "regarded him little", though it is unknown whether she knew this was the king. Henry then revealed his true identity to Anne, although he is said to have been put off the marriage from then on. Henry and Anne then met officially on 3 January on Blackheath outside the gates of Greenwich Park, where a grand reception was laid out.
Most historians believe that Henry's misgivings about the marriage were blamed on Anne's alleged unsatisfactory appearance and her failure to inspire him to consummate the marriage. He felt that he had been misled after his advisors had praised Anne's beauty: "She is nothing so fair as she hath been reported", he complained. Cromwell received some blame for the Holbein portrait, which Henry believed had not been an accurate representation of Anne, and for some of the exaggerated reports of her beauty. When the king finally met Anne, he was reportedly shocked by her plain appearance, and the marriage was never consummated.
Henry urged Cromwell to find a legal way to avoid the marriage but, by this point, doing so was impossible without endangering the vital alliance with the Germans. In his anger and frustration, the King turned on Cromwell, to his subsequent regret.
Anne of Cleves