Surviving Contemporary Portrait of Anne Boleyn

With a portrait of Anne Boleyn coming to light from the National Portrait Gallery of Ireland we take a look to determine if it’s contemporary, or not.

After her execution, anything that would remind Henry, or his subjects, of Anne Boleyn was destroyed. There are a few things here and there that were missed in the path of destruction but I have always read that there was no contemporary portraits of Anne that survived the destruction. We haven’t had anyway of knowing what Anne really looked like because the paintings or sketches that were labeled as her could not be proven to be so – even the sketches that Holbein created were labeled years after his death, so we cannot confirm.

Here are some (not all) of the portraits that have been said to be Anne Boleyn:

Historian Eric Ives (1931-2012) wrote a very well researched book about Anne Boleyn called, “The Life and Death of Anne Boleyn” that is regarded as the bible of Anne Boleyn by many researchers. He covered everything about her in his book, including her portraits. He also discussed those who willfully described Anne as different from what she was – here is an example:

Nicholas Sander, who was opposed to Elizabeth being queen of England, said this about her mother:

Anne Boleyn was rather tall of stature, with black hair, and an oval face of a sallow complexion as if troubled with jaundice. She had a projecting tooth under the upper lip, and on her right hand six fingers. There was a large wen under her chin, and therefore to hide its ugliness she wore a high dress covering her throat. In this she was followed by the ladies of the court, who also wore high dresses, having before been in the habit of leaving their necks and the upper portion of their persons uncovered. She was handsome to look at, with a pretty mouth.

Sander was only nine years old at the time of Anne’s execution – would he really have known all those things about her? Not to mention that in the above quote he contradicts himself describing her ugliness and then in the last sentence saying she was handsome to look at. Which was it, Sanders?

Ives also quotes George Wyatt, grandson of Anne’s friend, Sir Thomas Wyatt, describing Anne as well – Wyatt at least had family lore to go off of since his father surely had been told stories of Anne, but was this true? I’ve always believe that the extra nail thing was something that was made up by those who opposed Anne as queen.

…there was found, indeed, upon the side of her nail, upon one of her fingers some little show of a nail, which yet was so small, by the report of those that have seen her, as the work master seemed to leave it an occasion of greater grace to her hand, which, with the tip of one of her other fingers might be, and was usually by her hidden without any blemish to it. Likewise there were said to be upon some parts of her body, certain small moles incident to the clearest complexion.

The Holbein sketches were not labeled by Holbein himself, they are thought to have been labeled by Sir John Cheke (tutor to Edward VI). It was believed to have been proper labeling since Cheke actually knew Anne Boleyn, however, other sketches that Cheke labeled at the time have since been corrected. He may have been mistaken with these as well. The sketch on the right is normally said to have been out-of-character attire for a queen to be portrayed in.

The only known contemporary image of Anne Boleyn has always been said to be her “Moost Happi” medal that was created about 1534 when she was pregnant. It was expected to be released when she gave birth to a son. The one on the right is the surviving medal that was damaged. The medal on the left is the restoration of the medal.

“The Moost Happi” Medal of Anne Boleyn Restored | by lisby1

Some believe, including myself, that the medal best resembles this portrait of an older Anne Boleyn – this one also has not been confirmed as Anne but in my opinion close resembles the medal:

Historian Ives discusses some of the most well-known portraits and stated that all were made fifty to sixty years after her death, in late 16th century, during the reign of her daughter, Queen Elizabeth I.

Queen Elizabeth was said to have worn a ring that secretly displayed an image of her mother. The portraits inside were not discussed until after her death.

So the question remains, what did Anne Boleyn actually look like? Eric Ives believed that the “Moost Happi” medal sitter and that in the ring are the same person. With forty-five years between the two and a difference in headdresses, he still believes it is the same person.

Next up we have this portrait miniature of Anne that was in the collection of the Duke of Buccleuch and Queenberry. King Charles I had it copied as “Anne Boleyn” by John Hoskin the Elder. It had written on the back of the mounting – ”from an ancient origin”.

Lastly, let’s go back to the portrait from the National Portrait Gallery of Ireland of Anne Boleyn. The portrait is labeled as purchased by the gallery in 1903 and states that it was made by an unknown artist in the 16th century. What we do not know is which part of that century and who was the artist? If it was during her lifetime then we have an amazing find here, but I suspect it is like all the others – made during the reign of her daughter.

Portrait of Anne Boleyn (1507-1536), 2nd wife of King Henry VIII/Unknown Artist, England, 16th century/NGI.549


Ives, Eric; The Life and Death of Anne Boleyn
National Portrait Gallery of Ireland


Sanders, Schism, p.25
Singer, Wolsey, p. 424


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