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Henry VIII's Six Wives, Ranked By Which One Would Be The Best Wife

August 20, 2020 2.3k votes 419 voters 12.5k views6 items

List RulesVote up the brides of Henry VIII you'd most want to say "I do" to.

Divorced, beheaded, died, divorced, beheaded, survived - the six Henry VIII wives often lost more than they gained from marriage to England's most royal bachelor. But what did each of them bring to their marriage?

In his obsessive quest to produce a male heir, Henry VIII of England went through a series of wives. He annulled his marriage to Catherine of Aragon (m. 1509-1533), executed Anne Boleyn (m. 1533-1536), lost Jane Seymour (m. 1536-1537) to childbirth, annulled his marriage to Anne of Cleves (m. 1540), and beheaded Catherine Howard (m. 1540-1542). His final wife, Catherine Parr (m. 1543-1547), survived him by only a year.

Henry's wives were unique individuals with their own strengths and weaknesses, and some would have appeared to be better partners on paper than others. Each of Henry's six brides brought something to the marriage table, whether it was Anne of Cleves's political alliance, Catherine of Aragon's wealth, or Catherine Parr's personal qualities. But at the same time, every potential partner brought her own set of risks, since her family, religious beliefs, or political loyalties could cause clashes.

So, considering the pros and cons of what each woman offered, which of Henry VIII's wives would make the best bride?

  • Age: 31

    Dowry: None

    Interests And Skills: Catherine Parr was well educated and intelligent, and her accomplishments went far beyond what was generally expected of a Tudor gentlewoman. She was a scholar and published author in an era in which many women were illiterate.

    Mature, sensible, and kind-hearted, Catherine Parr would be an ideal companion. Another plus: Parr could bring stability to any family she joined, since she was a good, supportive stepmother to the surviving royal children. She even saw to it that Princess Elizabeth - who would become Queen Elizabeth I - had access to an education similar to that of her brother.

    Parr could also be a savvy political partner who could help shoulder the burden of ruling. She proved herself to be a capable ruler who had a hand in some of Henry's decisions and took the reins of government when the king was away.

    On the downside, Catherine Parr would have little to offer by way of foreign alliances. Plus, she was a bit overzealous in her Protestant faith - a fact that could heighten religious tensions in an already divided kingdom.

    • Age: Dec. at 36 (1512-1548)
    • Birthplace: Blackfriars, London, London, United Kingdom
    391
    41
    Marriage material?
  • 2

    Catherine Of Aragon

    Age: 23. She has the distinction of being the only one of Henry's wives whose exact birth date has been recorded.

    Dowry: Worth 200,000 crowns

    Interests and Skills: Catherine received a wide-ranging education appropriate for the daughter of Queen Isabella of Spain. She learned languages, literature, religion, and art. According to Sebastian Giustinian, the ambassador from Venice and a court observer, Catherine was "not handsome, though she had a very beautiful complexion. She was religious and as virtuous as words could express."

    Politically, Catherine of Aragon would be hard to beat as a potential bride. She had impressive connections to Spain and Rome, boasted a wildly extravagant dowry, and was a capable leader. 

    Considering her piety and resentment over Henry's mistresses, however, she wouldn't be an easygoing partner. Yet despite her religious conservatism, she didn't balk at a relationship that verged on incest: Catherine was Henry's sister-in-law before she was his wife. She had been briefly married to his older brother Arthur before he passed in April 1502, less than four months after their wedding. Henry had to get the pope's permission to marry his deceased brother's wife.

    • Age: Dec. at 50 (1485-1536)
    • Birthplace: Alcalá de Henares, Spain
    319
    83
    Marriage material?
  • Age: 25

    Dowry: Henry insisted that there was no need for a dowry

    Interests and Skills: Like Jane Seymour, Anne of Cleves loved stitching and doing embroidery. Since her mother directed her education, Anne was not as educated as some of her royal counterparts, though she was literate. 

    Kind, humble, and peaceable, Anne would be a remarkably good sport as a wife. After all, she graciously agreed to an annulment after only a few months of marriage and maintained a positive relationship with Henry until his passing in 1547.

    This was all despite Henry's callous treatment of her. He directed humiliating criticisms - which were painfully, unfairly, and wrongly personal - at her. Though Henry reportedly fell for her when he saw her portrait, he later insisted that she wasn't as good looking as she appeared in the painting. Henry - who would soon suffer from leg ulcers that emitted a foul smell - also complained about the "evil smells about her."

    Marriage with Anne of Cleves would make political sense. It could build an alliance with Protestant Cleves in order to check Catholic France and Spain's influence on the continent.

    Though Anne was sharp, she wasn't totally fluent in English when she arrived in 1540. This would make communication difficult for two people who didn't speak the same language. Due to her upbringing in Cleves, Anne also lacked some courtly accomplishments, such as musical proficiency, that English courtiers would expect of their queen.

    • Age: Dec. at 41 (1515-1557)
    • Birthplace: Düsseldorf, Germany
    272
    94
    Marriage material?
  • Age: 28

    Dowry: Though Jane Seymour didn't have much of a dowry, Henry gifted her with, in biographer Antonia Fraser's words, "104 manors scattered through 19 counties, five castles and a number of chases and forests, including Cranborne Chase, and the Paris Garden in London."

    Interests and Skills: Jane Seymour was a first-rate needleworker and Catherine of Aragon fangirl.

    Gentle and docile, Jane Seymour would make a drama-free spouse. Bonus: Her lack of drama would be politically expedient, too, since Seymour "represented no ideology," as biographer David Loades put it. 

    Unlike Catherine of Aragon or Catherine Parr's exceptional educations, Jane Seymour's education was more typical of a Tudor gentlewoman; she was, according to historian Alison Weir, "barely literate." While that makes for a peaceable spouse - she wasn't likely to fire off letters to nobles across the kingdom and coordinate a coup, for example - it also makes for a less cultured one.

    • Age: Dec. at 29 (1508-1537)
    • Birthplace: Wulfhall, United Kingdom
    187
    158
    Marriage material?