Most medieval monarchs left behind almost nothing reliable about their actual appearance. A stylized painting here, a flattering description there, none of it quite trustworthy. But Henry VII is the exception. Between a portrait painted from life, an eyewitness account from someone who knew him, and a death mask taken directly from his body after death, Henry VII’s face is one of the best-documented of any king from the period. Piece the evidence together, and a surprisingly human – and surprisingly candid – picture emerges.

Let’s analyze the sources for his appearance and reveal the re-creations!

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The Painted Portraits: The Portrait Painted to Win a Bride

One pillar of evidence hangs today in London’s National Portrait Gallery, where it holds the honor of being the oldest painting in the entire collection. An inscription dates it to the day: finished on October 29, 1505, by an unknown Netherlandish artist.

It wasn’t painted for vanity. Two years after the death of his wife, Elizabeth of York, Henry was in the market for a second marriage, and his people were negotiating with Margaret of Savoy, daughter of the Holy Roman Emperor. The painting was commissioned by the emperor’s agent and shipped abroad so the prospective bride could see exactly what she’d be getting.

She eventually said no. But she kept the painting anyway – and because of that, we have a life portrait of a 48-year-old Henry that historians consider the single most reliable image of him in existence, the template most later copyist would trace back to, some more convincingly than others.

A Description From Someone Who Actually Knew Him

Portraits can flatter. Words sometimes, tell the truth more plainly. Henry commissioned the Italian scholar Polydore Vergil to write a history of England, and around 1513, Vergil, who had actually spent time with the king, left behind a written portrait to go alongside the painted one.

He described a young Henry as attractive and animated, especially when talking about his plans for the country: slender but strong, taller than average, with brownish-red hair and dark blue eyes.

Henry was a smart man – a man genuinely interested in the realm he was ruling, the woman he was ruling it with, and his children, including the future Henry VIII and Arthur Tudor.

But the years wore on him. By the end of his reign, that same king had grown pale and reclusive, hunching over his ledgers like an obsessed jeweler. His hair turned white, and his teeth rotted away. He was a man aged by decades of anxious, obsessive rule, and the death of his beloved wife, Elizabeth of York, in 1503.

Here’s the full text from Vergil:

His body was slender but well built and strong; his height above the average. His appearance was remarkably attractive and his face was cheerful, especially when speaking; his eyes were small and blue, his teeth few, poor and blackish; his hair was thin and white; his complexion sallow. His spirit was distinguished, wise and prudent; his mind was brave and resolute and never, even at moments of the greatest danger, deserted him. He had a most pertinacious memory. Withal he was not devoid of scholarship. In government he was shrewd and prudent, so that no one dared to get the better of him through deceit or guile. He was gracious and kind and was as attentive to his visitors as he was easy of access. His hospitality was splendidly generous; he was fond of having foreigners at his court and he freely conferred favours of them. But those of his subjects who were indebted to him and who did not pay him due honour or who were generous only with promises, he treated with harsh severity. He well knew how to maintain his royal majesty and all which appertains to kingship at every time and in every place. He was most fortunate in war, although he was constitutionally more inclined to peace than to war. He cherished justice above all things; as a result he vigorously punished violence, manslaughter and every other kind of wickedness whatsoever. Consequently he was greatly regretted on that account by all his subjects, who had been able to conduct their lives peaceably, far removed from the assaults and evil doing of scoundrels. He was the most ardent supporter of our faith, and daily participated with great piety in religious services. To those whom he considered to be worthy priests, he often secretly gave alms so that they should pray for his salvation. He was particularly fond of those Franciscan friars whom they call Observants, for whom he founded many convents, so that with his help their rule should continually flourish in his kingdom, but all these virtues were obscured latterly only by avarice, from which…he suffered. This avarice is surely a bad enough vice in a private individual, whom it forever torments; in a monarch indeed it may be considered the worst vice, since it is harmful to everyone, and distorts those qualities of trustfulness, justice and integrity by which the state must be governed.

From Polydore Vergil, The Anglia Historia, 1485-1537 

A Death Mask and Two Sculptures

Unlike his wife, whose death caught the court off guard, Henry’s death was anticipated well in advance. That meant there was time to do the practical things like planning a tomb and the chapel it would lie in, planning the funeral and procession, and in this case – taking a cast directly from his face after he died.

Sculptor Pietro Torrigiano used that death mask to build two separate images of the king in the years after his passing – a bronze effigy that would sit atop his tomb, and a strikingly lifelike terracotta bust, both created as part of the elaborate tomb Henry himself had helped design before he died.

The tomb sits as planned, in beautiful shape, in Westminster Abbey’s Lady Chapel.

The Effigy That Almost Didn’t Survive

The most compelling piece of evidence, though, isn’t a sculpture at all — it’s a funeral prop. When Henry died, craftsmen built a life-sized figure of him to lie atop his coffin during the funeral procession: robed, crowned, holding an orb and scepter, roughly six feet of wood, straw, canvas, and plaster, its face modeled from that same death mask. It now resides in Westminster Abbey next to Elizabeth of York’s, where it stuns visitors every year.

Only the head survives today, and it barely made it. Like similar Tudor-era effigies, it spent years damaged, tangled in a pile of other effigy parts, stashed in a flooded storage space before conservators at Westminster Abbey were able to restore it.

What’s left, though, is remarkably human: one eye sits slightly lower than the other, and there’s a real, unpolished determination in the set of the jaw – details a formal sculpture might have smoothed away.

The Mystery of the Nose (and the Missing Dimple)

But here’s something curious. The effigy’s nose was so badly damaged that restorers had to rebuild it. First, the rebuilt it using a cast taken from Torrigiano’s bronze, only to find that version was far too long and narrow to fit the face. So they tried again, this time basing it on the terracotta bust, which fit better, though conservators still noted it looked unusually heavy.

More curious still: Torrigiano’s sculptures leave out a small dimple in Henry’s chin (which restorer Howgrave-Graham charmingly calls a “pleasant little dimple”) that shows up clearly on the death mask and faintly in the 1505 portrait. And technicians restoring the effigy found real human hair (although it’s surely not actually Henry’s) still stuck to its head – a mix of bright red and grey, a detail nowhere to be found in the surviving portraits, where his hair reads as a much darker brown.

These are just small inconsistencies to the casual history observer. But to me, they are not. Henry was, after all, one of history’s more skilled self-mythologizers . He was the king who invented the Tudor rose, spun the legend of a crown plucked from a hawthorn bush, and commissioned ballads about his own victories being ordained by God. Tudor England also had a deep-rooted belief in physiognomy: the idea that a person’s virtue could be read in their face, with pale skin, blue eyes, and a strong, elegant nose treated as signs of nobility and legitimacy.

It raises a genuine open question – did Torrigiano quietly idealize the king’s features to project authority and legitimacy? Did Henry order him to? Or were these simply the ordinary gaps and artistic errors that creep into any centuries-old restoration?

Either way, the sheer amount of surviving evidence – a life portrait, an eyewitness account, a death mask, and multiple sculpted likenesses – makes Henry VII’s face about as close to certain as it gets for a medieval king. Few monarchs from this era can be reconstructed with this much confidence, and fewer still leave behind quite this many small, human contradictions to puzzle over.

The Facial Reconstructions