Reimagining The Wives Of King Henry VIII
Today, we know the six wives of Henry VIII more by the phrase "divorced, beheaded, died; divorced, beheaded, survived" than we do by their own names and legacies. But Catherine of Aragon, Anne Boleyn, Jane Seymour, Anne of Cleves, Catherine Howard, and Catherine Parr were more than historical curios—they were real people.
Using AI renderings, we can now look at paintings of the Queens—or historians' best guesses—to create modern images of the women and breathe new life into them. Let's start with the historical painting and then move to the rendering for each Queen chronologically, giving illuminating details along the way.
Catherine of Aragon
16 December 1485–7 January 1536. Married King Henry VIII in 1509, annulled 1533.
The first of King Henry VIII's Queens, people called Catherine of Aragon "the most beautiful creature in the world" in her youth, and Thomas More claimed "there were few women who could compete with [her] in her prime". This portrait by Michael Sittow, perhaps of Catherine, was taken around 1502 when she was 17 years old. What would this girl look like today?
Michael Sittow, Wikimedia Commons
Catherine of Aragon Reimagined
Catherine of Aragon was six years older than her husband and had been married first to King Henry's older brother Arthur, before Arthur died. Although Catherine was the longest-serving of Henry's Queens, she never gave him the healthy male heir he wanted, and only her daughter Mary lived to become Queen Mary I.
After more than two decades of marriage, Henry would eventually (and with great difficulty) annul their union in favor of marrying his next Queen...
Anne Boleyn
1501 or 1507–19 May 1536. Married King Henry VIII in 1533, executed 1536.
Anne Boleyn is perhaps the most famous and most tragic of Henry VIII's queens. Reportedly charismatic and unconventionally attractive, Anne secured her crown by refusing to bed Henry (who wanted her as his mistress) until he married her. But after their relationship went sour, Henry had all portraits of Anne destroyed, and what we now have are copies of originals.
The one here was originally a posthumous portrait, and represents her somewhere between the age of 29 and 35.
English school, Wikimedia Commons
Anne Boleyn Reimagined
Anne and Henry's relationship was always volatile, and—worst of all—she too never gave Henry a son. (She did, however, give England her daughter, Queen Elizabeth I.) After becoming fed up with her, Henry had Anne executed for charges of adultery and treason, among others.
Jane Seymour
c. 1508–24 October 1537, Married King Henry VIII in 1536, died 1537.
Of all King Henry VIII's wives, Jane Seymour was the only one to give him a healthy boy, the future King Edward VI. Although she fiercely vied with Anne Boleyn for Henry's attention while Anne was still alive, today Jane is portrayed mostly as a mild-mannered, angelic-looking woman. The Tudors, however, thought differently.
Though some curried favor with Henry by saying she was "a woman of the utmost charm in both character and appearance," one courtier thought she was only middling in height, too pale, and not a beauty. This painting from Hans Holbein the Younger helps reconstruct her looks.
Hans Holbein the Younger, Wikimedia Commons
Jane Seymour Reimagined
In the end, giving King Henry VIII a male heir was exactly what led to Jane Seymour's downfall. Just a year after her marriage, she died from complications of the childbirth. Nonetheless, she remained in Henry's thoughts for the rest of his life; when he died, he requested to be buried beside her.
Anne of Cleves
28 June or 22 September 1515–16 July 1557. Married King Henry VIII January 1540, annulled six months later.
Anne of Cleves gets an especially bad historical reputation, looks-wise. After all, many widely consider her Henry's "rejected" Queen. Although court portraitist Hans Holbein the Younger painted the flattering portrait we see of her here, when Henry saw her he was reportedly unimpressed, and ended up quickly annulling the union.
But was she really as ugly as they say?
Hans Holbein the Younger, Wikimedia Commons
Anne of Cleves Reimagined
Although Henry's comments about Anne indicate he was physically repulsed by her, some historians suggest a more disturbing reason for his disgust. Before they were to officially meet, Henry disguised himself and crept into Anne's lodgings, expecting her to recognize him if they were "fated" to be together. When, instead, she grew alarmed, it's possible Henry held a grudge forever after.
So even though we should take her portrait with a grain of salt, we should also be suspicious of Henry's account of Anne of Cleves.

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Catherine Howard
c. 1523–13 February 1542. Married King Henry VIII in 1540, executed 1541.
Catherine Howard is one the most elusive of Henry VIII's Queen in terms of her portraiture. There is no absolutely confirmed likeness of her available in history. However, this portrait by Hans Holbein the Younger stands a fair chance of being the young girl, who married Henry when she was still a teenager. Unfortunately, it didn't go well for her.
Hans Holbein the Younger, Wikimedia Commons
Catherine Howard Reimagined
In the end, Catherine Howard was too young for the burden of the throne, and Henry—now obese and ailing—was too old to hold his teen bride's attention. Before long, Catherine found herself in a romance with a courtier. When her dalliance was found out, she went to the chopping block before her 20th birthday.
Catherine Parr
c. July or August 1512–5 September 1548. Married King Henry VIII in 1543, survived him.
Now world-weary and seeking stability, Henry VIII chose the more mature, twice-widowed Catherine Parr for his next (and final) wife. With Catherine in her 30s, Henry likely didn't pick her for her ability to bear him a son, but instead for her ability to care for him as he approached old age. Catherine died at 36; this portrait depicts her no later than that age.
National Portrait Gallery, Wikimedia Commons
Catherine Parr Reimagined
In the end, Catherine only had to act as nursemaid to Henry for a handful of years. The King died in 1547 after less than four years of marriage. After Henry, Catherine remarried again—at four husbands, she is the most married English Queen.
Even so, surviving Henry wasn't easy: A year before his death, they had a tiff, and Henry had an arrest warrant for Catherine drawn up, only to drop it when they reconciled.
Henry VIII
Now, what of Henry himself? Finding a representative portrait of the King can be difficult. Not only were court portraitists seeking his favor, but Henry's physicality changed greatly over the years, especially after a jousting accident caused him a leg injury.
This portrait by Joos van Cleve was painted circa 1530-35, just before the injury, and represents a healthy Henry nonetheless approaching middle age.
Royaltynow, CC0, Wikimedia Commons
Henry VIII Reimagined
Was this the face that launched a thousand bids for his hand? Perhaps. We do know that Henry had auburn hair (it ran in the family), a curious and artistic mind, and a sportsman-like physicality until time got the better of him.
Living History
What do you think about these renderings of King Henry VIII's Queens and Henry himself? What do you think of their lives and legacies? Let us know.
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