26 of the Most Unflattering Royal Portraits Ever

Did you think the artists that painted royalty had to make them look beautiful? Think again! Some royal portraits are outright mean. Take a look at some of the most unflattering royal portraits:

1. Marguerite of Burgundy, Princess of France. Painted c. 1400

Unflattering royal portrait of a woman. She is young, very pale, has a very long, thin, asymmetrical face. She has smallish, drowsy eyes.
Unknown painter. (Photo: Wikimedia/Public domain)

2. Lorenzo de’ Medici, Lord of Florence. c. 1485

Very unflattering portrait of a royal middle-aged man. He has an overly prominent lower jaw and looks a bit brutish.
Painting by Giorgio Vasari. (Photo: PDArt//Public domain)

Lorenzo was not technically a royal, but his powerful family ruled the city of Florence for generations.

Lorenzo the Magnificent was a great ruler and a patron of the arts. From other paintings and his death mask, he did seem to have had, let’s say, strong features.

Keep an eye out for more strong-featured members of the Medici family below.


3. Louis XI, King of France. 1469

A man seen from the side. His nose is very big and droops downwards.
Painting by Jacob de Littemont. (Photo: Wikimedia/Public domain)

4. Isabella I, Queen of Castilla. c. 1500

Unflattering portrait of a woman. She is quite plain and looks bored. Her eyes are half-asleep. None of her features are pretty.
Painting by the Spanish School. (Photo: Wikimedia/Public domain)

Isabel is the famous queen who financed Christopher Columbus’ adventures in the New World.

She was the queen of Castile, while her husband was the king of Navarra. The power couple united their kingdoms and conquered the neighboring ones. With that, they united Spain. Furthermore, thanks to the territories in the New World, Spain became an empire.

Read next: How Many Continents Are There: 5, 6, 7…? Was Your Teacher Wrong?

5. Charles V, King of Spain, Holy Roman Emperor. 1515

An unfortunate portrait. The king has tiny eyes and a very long face. His chin is absurdly prominent.
Painted by the Flemish School. (Photo: Hampton Court Palace/Public domain)

Charles is the first Habsburg to appear on this list, but he will certainly not be the last. The Habsburgs were a prominent family that at one point ruled most of Europe.

Charles V was a powerful monarch. And he was the grandson of Queen Isabel of Castile, who we saw at #4.


6. Ferdinand I, Holy Roman Emperor. 1500

A man with big eyes, longish face, crooked nose.
Painting by Jan Cornelisz Vermeyen. (Photo: Didier Descouens/Public domain)

Ferdinand was Charles V’s brother (#5). He inherited the throne of the Holy Roman Empire from Charles and ruled other countries.

7. Henry VIII, King of England. 1544

The man pictured does not even look fully human. It is a bad portrait. He has a square, big, flat face. His eyes are impossibly wide-set. His nose is smallish and his mouth is tiny.
Artwork by Corneille Metsys. (Photo: Wikimedia/Public domain)

You probably know about Henry VIII. Between his feat of changing the religion of a whole country to marrying six times -and beheading several wives- he tends to make a lasting impression.

Henry had a compelling personality. And he was said to be quite handsome, even if this painting does not show it. During the last years of his life, he did gain weight and suffered health problems. Yet, other artists are kinder, or perhaps more skillful, when portraying him during his later years.

8. Elizabeth I, Queen of England. c. 1593 and 1595

Elizabeth was the daughter of Henry VIII (#7). She was one of England’s greatest monarchs.

9. Francis, Prince of France, Duke of Anjou. 1557

A young man with a triangular-shaped face. His forehead and nose are too big for his face. He has small eyes.
Painting by Nicholas Hilliard. (Photo: The Yorck Project/Public domain)

The Duke was the son of the king of France. And he was one of the many suitors of Queen Elizabeth I of England (#8).

Francis visited her twice in London, and the pair grew close. Elizabeth had received reports of Anjou’s unappealing physical features. But after meeting him, she said the reports had been exaggerated.

She seems to have wanted to marry him, but her English subjects were not keen on having a foreign king. So Elizabeth, who was in her forties, gave up the idea with sadness.

Francis was a Medici (#2) through his mother, Catherine de’ Medici.

10. Maria Anna of Bavaria, Archduchess of Inner Austria. 1600

An unflattering portrait, probably due to lack of skill of the painter. The woman is older, she has a plain face with heavy-lidded, dull eyes. Her nose is long and crooked. Her jaw is wide and has a double chin. She wears black mourning clothes.
Unknown painter. (Photo: Wikimedia/public domain)

Maria Anna was the granddaughter of Ferdinand I (#6). She was a Habsburg.

11. Christina, Queen of Sweden. c. 1650

A young woman with big, protruding eyes which slant down at the corners making her look sad. Her nose is big and crooked, her mouth has a protruding lower lip.
Painting by Sebastien Bourdon. (Photo: National Museum of Sweden/Public domain)

Christina was the reigning queen of Sweden. She was highly educated and intelligent, but she did not like to govern. So she eventually abdicated and exiled herself in sunny Italy. She converted to Catholicism and became friends with the pope, even though she flaunted her same-sex relationships.


12. Prince Leopoldo de’ Medici. c. 1655

A man with a very long face. His eyes are big and bulging, his nose is big and aquiline. His lips are thick. His lower lip and his chin protrude. He is wearing a cardinal's red robes.
Painting by Justus Sustermans. (Photo: Wikimedia/Public domain)

Leopold belonged to both the Habsburg and the Medici families.

Since his grandfather was the ruler of Austria, Leopold was born a prince. But he joined the Church and became a cardinal. Leopold was an intellectual and was especially fond of the sciences. He was also a great book and art collector.

13. Leopold I, Holy Roman Emperor. 1670 and 1672

Another Leopold, another Habsburg. This Leopold’s father was a Holy Roman Emperor, and his mother was a Spanis princess. Both his parents were Habsburgs.

Leopold was Holy Roman Emperor and king of Hungary, Bohemia, and Croatia. He started several wars.

14. Margaret Theresa, Holy Roman Empress. 1667

A sweet-looking blonde blue-eyed girl. Her forehead is too big for her face. Her nose too. Her lips are thick but the shape of her mouth is not appealing.
Painting by Jan Thomas. (Photo: Kunsthistorisches Museum Wien/Public domain)

Margaret Theresa was a Spanish princess. And she was a Habsburg through both her parents.

Margaret married Leopold I, who we just saw above (#13). Since Leopold too was a Habsburg, he was Margaret’s maternal uncle and paternal cousin. The duo was related several more times, but the genealogy gets confusing.


15. Charles II, King of Spain. 1680

A young man. He looks like the previous girl but his features are tougher. He too has long blond hair and big eyes. His nose is big and bulbous. And his jaw protrudes along with his chin.
Painting by Juan Carreño de Miranda. (Photo: Kunsthistorisches Museum Wien/Public domain)

Charles II was Margaret Theresa’s brother (#14). Since his family, the Habsburgs, were so inbred, Charles was born with many physical disabilities. He suffered ill health all his life and died at 38.

16. Ulrika Eleonora, Queen of Sweden. 1676 and 1690

Thanks to Ulrika, we can take a break from the Habsburgs. Ulrika’s father was the Danish king. And upon marriage, she became the queen consort of Sweden.

Although her husband complained about her looks upon meeting her, the couple went on to have a happy and loyal marriage. Ulrika was described as wise, wonderful, and kind.

17. Cosimo III de’ Medici, Grand Duke
of Tuscany. c. 1712

An unkind portrait of an older man. He has white, long hair. His face is long. His eyes, nose, and lips are huge.
Unknown painter. (Photo: Wikimedia/Public domain)

Cosimo was both a Medici and a Habsburg.

18. Ulrika Eleonora, Queen of Sweden. c. 1719

A woman with a kind face. She is smiling. She has nice, big eyes, but her nose is too big an aquiline.
Painting by Georg Engelhard Schröder. (Photo: Bukowskis/Pubic domain)

This Ulrika is the daughter of the Ulrika we saw above (#16). She inherited the Swedish throne and ruled for two years. Then she abdicated in favor of her husband.

19. Peter III, Tsar of Russia. 1753

A young man with an oval, long, pale face. His eyes are small and too wide-set. His nose is long.
Painting by Aleksey Antropov. (Photo: Wikimedia/Public domain)

Peter was a relation of Ulrika, the reigning queen of Sweden (#18)

Peter III was the tsar briefly. His ambitious wife took his throne, got rid of Peter, and became tsarina herself.


20. Catherine the Great, Tsarina of Russia. c. 1740

A young woman with a triangular-shaped face. Her eyes are wide-set and uneven. She is cross-eyed. She has a long, aquiline nose. Her mouth is small, and her chin is long and pointy.
Painting by G.C.Grooth. (Photo: Wikimedia/Public domain)

Catherine was the wife of Peter III (#19), so she is the ambitious woman we were just talking about. She took Peter’s throne and became an extraordinary ruler. If she resembles her husband Peter, it is because they were cousins.

Catherine was not a great beauty. But unlike other artists, Grooth, who painted this portrait, tended to be unforgiving when portraying her. Even her big blue eyes that were one of her great assets are neglected here. Maybe he was secretly #teamPeter?

Read more: Catherine the Great Was Friendly and Easy-going- The Tsarina’s Temperament and Looks

21. Mariana Victoria, Queen of Portugal. 1760

She has a harsh, stern face better suited for a man. Her face is squared, her forehead is very high, her eyes and nose are small.
Painting by Miguel António do Amaral. (Photo: Wikimedia/Public domain)

22. Charles III, King of Spain. 1765

He looks kind and is smiling. He wears a white wig. His face is small. He has shiny eyes and a huge nose.
Painting by Anton Raphael Mengs. (Photo: Wikimedia/Public domain)

Charles was a capable and strong ruler who was respected by his people. He was from the house of Bourbon.

23. Charlotte Amalie, Princess of Denmark and Norway. c. 1760

She looks sweet. Her face is triangular. Her forehead is too high. Her big-blue eyes are pretty, but the combination of big nose, small mouth, thin jaw with prominent chin is not working for her.
Painting by Peter Wichmann. (Photo: Orf3us/Public domain)

Charlotte’s contemporaries spoke highly of her. They said she was lovable and a born-diplomat.

24. Philip, Prince of England. 2004

He looks pretty much like the real Prince Philip, but his features have been exaggerated, like those of a caricature. The prince's torso is nude , he has a fly on his shoulder, and he is raising his right hand. From one of his fingers sprout 4 saplings.

Prince Philip sat four times for this painting.

During the fourth sitting, the nervous artist asked Philip if he had been able to capture his image. The witty Prince quipped: “I bloody well hope not.”

And that was the end of the sittings. The artist finished the painting in his studio. And then presented it to the Royal Society for the Encouragement of Arts, since they had commissioned the work. But the Society deemed the portrait ‘inappropriate.’

They were not alone. The public also found it undignified and unflattering. After all, they argued, Philip is a prince by birth and is the husband of reigning Queen Elizabeth of England. So the artist did another version of the portrait without nudity, flies, or sprouting finger. That one hangs at the Society.

Despite the fallout, the Prince himself had chosen Stuart Pearson Wright, the artist, to paint him. It is not surprising since Pearson is talented, creative, and has superb technical skills. Some people do like this painting and think it shows Philip’s vulnerable side. And one of Pearson’s admirers bought it.

Just in case you were wondering, Philip was fully clothed while he posed for the piece. And, according to Pearson, the four saplings springing from the Prince’s (phallic?) finger represent his four royal children.

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25. Elizabeth II, Queen of England. 2001

This a close-up of the queen's face. The brushstrokes are thick and pasty, and have not been blended into each other. So the result is a harsh-looking face.
Painting by Lucien Freud.

The current Queen of the United Kingdom has also been the victim of unflattering portraits. Or at least the British public thinks so. They took special offense with this one.

The painting was made by ultra-famous artist Lucien Freud -a relation to that other Freud.
Lucian is admired around the world for his frank, depressive, and isolating paintings. He does not do pretty. Ever. So the queen must have had a good idea of what she was in for when she sat for him. And she seems to be happy with the result for it hangs in one of her palaces. The portrait is probably worth tens of millions.


26. William, Prince of England. 2014

A man with a long, rectangular face. His forehead is rather high, his eyebrows sit at different heights, his blue eyes too. One eye is slightly smaller than the other. His nose curves to one side, his mouth does so even more. His face is not symmetrical.

This portrait got quite the backlash too. Many members of the public called it “terrible.”

A young, up-and-coming artist painted Queen Elizabeth II (#25), who sat for him. The following year her portrait was unveiled, and at the ceremony the artist, Dan Llywelyn Hall, met Elizabeth’s grandson, William.

Llywelyn decided to paint William as well, although the prince never sat for him. The painter spent three months finishing this work. He called it ‘Fatherhood’ because the prince had just become a father and the painting was meant to capture the worries of parenthood. It was sold to a foreigner and all the proceeds were donated to charity.

Which portrait was the most unflattering?

Extra question: Are the portraits of Queen Elizabeth and Prince William unflattering or are they masterpieces?

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