How Howard Pyle Shaped the Iconic Look of Pirates (Including at Disneyland!)
- Dr. Lauren Kilroy-Ewbank
- Mar 18
- 4 min read
Updated: 7 days ago
When you imagine a pirate, what do you see? I bet it is someone wearing a red sash and a tricorn hat, holding a sword or pistol, perhaps dawning an eye patch and a parrot on their shoulder. A treasure chest is likely close by. Does what you envisioned look something like the illustration above? I'd wager it did!
Did you know that this iconic look of pirates owes a lot to the artist Howard Pyle (who died in 1911) and his vivid imagination because this isn't really how pirates dressed? Pyle's art has been wildly popular though, influencing everything from storybook illustrations to the Pirates of the Caribbean at Disneyland.
Howard Pyle and the Brandywine School
Not long ago, Howard Pyle was a household name in the United States, and his fame stretched worldwide. His stories and illustrations captured U.S. readers, with the likes of Mark Twain himself eagerly anticipating Pyle's next publication. Pyle's stories explored tales of pirates, princesses, and patriots, including King Arthur, Robin Hood, pirate treasure seekers, and heroes of the American Revolution. [1] In his lifetime, he wrote and illustrated 23 books, as well as lent his artistic talents to support the works of other authors. Pyle's stories and images also appeared in magazines like Harper's. The man's work was everywhere!
Fun fact: Burying treasure was NOT a common pirate practice, but it was popular with 19th-century authors like Robert Louis Stevenson and Washington Irving!
He would also open an art school after he taught at several institutions. Called the Brandywine School because of its proximity to a Revolutionary War site with the same name, Pyle's school was filled with students. Many artists, including Norman Rockwell, became obsessed with his vision and art. Pyle's goal with his school was to create an American art school. While he wasn't as successful as he might have wished, he still, to this day, is known as the "Father of American Illustration." Many people, including Walt Disney, remained enchanted by his work even after he died in 1911.
"Do you know an American magazine Harpers Monthly? There are wonderful sketches in it…which struck me dumb with admiration…by Howard Pyle."—Vincent van Gogh in a letter to his brother Theo
Pyle's Inspiration for Pirates
People especially loved Pyle's adventure and historical stories, such as his Book of Pirates from 1903. Pyle was fascinated with pirates, and his stories and illustrations spawned many pirate lovers. And wouldn't you know it, but his vision of what pirates looked like has remained the de facto idea of pirates to this day. From Treasure Island to Captain Hook or Johnny Depp as Captain Jack Sparrow in Pirates of the Caribbean movies, Pyle's images are the direct inspiration. Pyle's most famous student, N. C. Wyeth, illustrated the most famous pirate book, Treasure Island by Robert Louis Stevenson, and Wyeth's images drew from Pyle's work as well.
His idea of a pirate is filtered through his imagination and the nineteenth century, which turns out was very different than the functional type of clothing that pirates of the 17th and 18th centuries wore.
Pyle borrowed from exoticized images of Roma people ("gypsies") and rogues made in the 19th century, then paired that with seafaring imagery.
Exotic fantasies of Spanish gypsies included people wearing sashes and headscarves, as well as jewelry like earrings.
Gypsies were wildly popular subjects in the Romantic era of the 19th century, so it is no wonder that Pyle drew inspiration from them. Add a beach or the ocean and a few other exotic elements, like a parrot, and voilá! You have Pyle's image of the pirate that has proven to be so pervasive that there is no overturning it.
Look at this image of a pirate, painted by Pyle in 1909, called Marooned. The lonesome pirate, marooned on a beach, sits with his head lowered. He wears a red sash and a head scarf. And do you notice his buckled shoes? That's another thing we associate with pirates (hello, Captain Hook!).
Pyle Created the Iconic Look of Pirates
Before Howard Pyle, pirates and buccaneers were shown as gentlemen in finer coats or as more ragged sailors. In reality, pirates probably wore practical clothes that would not get caught in ropes and would dry quickly while also keeping them warm.
Pyle's image of a pirate with sashes, bandanas, tricorn hats, and bright red additions, all while standing in dramatic poses or marooned on a beach, is a break from earlier traditions. Likewise, his emphasis on buried treasure, adventure, and even lawlessness have become prevalent in pirate lore.
We can see the enduring influence of Pyle on Walt Disney and his team of Imagineers like Marc Davis. If you have ever sailed the Caribbean seas at Disneyland's Pirates of the Caribbean, then it is as if Marc Davis and others transformed Pyle's visions into three dimensions to create an immersive experience. The pirate look, the poses, the action and adventure, the general pirate shenanigans—these all trace back to Pyle (though not solely!).
So the next time you ride Pirates of the Caribbean, or rewatch Disney's franchise, or even watch Captain Hook, look for traces of Pyle's influence.
Notes:
[1] Jill P. May and Robert E. May, Howard Pyle: Imagining an American School of Art (University of Illinois Press, 2011), ix.
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Learn more:
Howard Pyle's Book of Pirates: https://www.gutenberg.org/files/26862/26862-h/26862-h.htm
John Edward Dell, ed. Visions of Adventure: N. C. Wyeth and the Brandywine Artists. Watson Guptill, 2000.
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