The "Moost Happi" medal is the sole surviving contemporary portrait of Anne Boleyn that we know of. It's badly damaged, so it's a source of frustration for people who want to know the true appearance of Anne Boleyn.
The most commonly recognized portraits of Anne - the National Gallery portrait and the Hever Castle portrait - were created during the reign of her daughter, and may have been intentionally designed to look like Elizabeth. They may bear very little resemblance to the real Anne Boleyn.
Another portrait - a sketch by Holbein - is labeled as being Anne Boleyn (and is accepted as being an authentic portrait of her by the Royal Collection) but many people insist it can't be Anne because the heavy jawline, double chin, and light auburn hair do not match the more "accepted" version of her appearance. Go to this website to see a side-by-side comparison of the two Holbein sketches labeled as Anne Boleyn.
Elizabeth seems to have accepted something close to the Holbein portrait as an authentic likeness of her mother, if her portrait ring is to be believed.
But now, we may be closer to the true face of Anne Boleyn. Using facial-recognition software, Amit Roy-Chowdhury of the University of California, Riverside, has matched the portrait medal to an extant painting of Anne Boleyn. And the closest match to the medal is a portrait that has been long-dismissed as being a true likeness: the Nidd Hall portrait. Research on the subject is not complete, but the association is very interesting.
The Nidd Hall portrait isn't flattering. The sitter wears an English-style gable hood, and is identified as Anne by the AB brooch pinned to her gown. But the face with its long nose and receding chin is so different from our "accepted" image of Anne that for a long while, experts have suggested that it was a portrait of Jane Seymour re-touched during the reign of Elizabeth to turn it into a portrait of Anne.
This link has a superimposed slider which allows you to compare the image to the portrait medal.
Some of the jewelry the sitter wears shows up in portrait of Henry's other queens.
Jane Seymour wears the ropes of pearls across her bodice, and Kateryn Parr wears the tri-stone pendant.
The Nidd Hall sitter may also be wearing the "consort's necklace" all of Henry's queens after Anne were painted wearing.
Like the National Portrait Gallery version and the Hever Castle portrait, the Nidd Hall painting was created at least fifty years after Anne Boleyn's death. Unlike the prior two examples, the Nidd Hall portrait was obviously based off of a different "pattern."
The NPG and Hever portraits are supposed to be based off of the same painting ("B" necklace pattern) as the Hoskins miniature. Some suspect the original was a lost Holbein, or the portrait which belonged at one point to Lord Lumley.
It's possible that the positive identification of the Holbein sketch, Lucy Churchill's reconstruction of the portrait medal, and the identification of the Nidd Hall portrait have brought us closer to the true face of Anne Boleyn.
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