Costumes are an essential component of the pirate persona. Every detail, from the bandanas on their heads to the boots on their feet, emphasizes a flamboyance central to the pirate’s rakish appeal in the popular imagination. However, the historical accuracy of many of these items is questionable.
Pirates wore low-heeled leather shoes with buckles. While captains and officers may have occasionally worn boots, they would not have been practical for life on the high seas. For the same reasons, many lower-ranked crew members worked barefoot, especially in warmer weather.
This article will describe everyday items from a pirate’s wardrobe and briefly examine some potential sources of historically inaccurate representation.
Practical Considerations That Informed Pirate Footwear
Since the visual presentation was an important part of image-building, many infamous pirates were known to flaunt extravagantly flamboyant styles. For instance, Captain Bartholomew “Black Bart” Roberts’ scarlet long coat was so iconic that he was known as ‘le jolie rouge.’ 
But, while a few pirate captains and officers may have worn knee-high boots ashore, it is unlikely they did so at sea.
While Captains did not often have to venture onto the lower decks or scamper up riggings, they would still have patrolled the upper decks. Their work would have been demanding, even in the best weather. Boots would have been very impractical for ship life.
A pirate would need comfortable and hardy shoes to withstand the rigors of life at sea.
In all likelihood, they wore the type of round-toed, low-heeled leather shoes favored by other sailors of their day. These would have been secured by either laces or an easy-to-secure buckle and offered sufficient protection from cold weather, especially when worn over woolen stockings cut out of broadcloth. 
Many pirates of the lower ranks may have even gone barefoot when on deck. Especially when climbing up masts to hoist sails and secure rigging, shoes would have impeded the pirate’s job. They would have also been uncomfortable in warmer weather.
Pirate Clothing Explained
As with shoes, the selection of most items of pirate clothing would have been informed by practical considerations. As with other pirate possessions, they would most likely have been appropriated by theft. For these reasons, experts believe pirate costumes would not have differed significantly from those of other seamen of their day.
Durable and inexpensive linens and wool were the materials of choice for sailors of the 17th and 18th centuries. Specific variants used included broadcloth, “Welsh plains,” and “cotton,” which was really a type of wool. 
These materials would have kept the pirates cool in hot places and seasons and warm in the cold. With regular patching up, they would have also lasted for many years.
At the same time, canvas and kersey – a waterproof fabric – would also have been invaluable for life at sea.
Most pirates wore loose collarless long-shirts open at the top. These would have been tucked into baggy breeches – which could be hoisted up to the ankles when working – to make up for lack of underwear. A pirate’s breeches would likely have had pockets for coins and tobacco.
Over these, a pirate would typically wear a woolen waistcoat and a well-fitted short jacket that would allow easy movement and avoid getting caught in other equipment as they worked. On their heads, they wore knitted caps to keep warm and dry.
Notably, the few female pirates wore the same clothes as male pirates. Women’s clothes of the day would have been highly impractical for life on a ship.
Color Choices and Embellishment
Most lower-rank pirates would have worn colors similar to ordinary sailors. Whites, grays, tans, blues, and greens were common, as were striped and checked patterns. They might have accessorized these with more colorful scarves that could double up as protection for their heads from the heat.
Captains and higher-ranking officers would have had their pick of any expensive belongings captured from their enemies. So silk scarves, ornate hats, and long coats with long rows of shiny buttons were more likely to fall into their hands.
Many of the accessories that pirates are said to have worn – such as eyepatches, earrings, and bandanas – are now thought to be based on fictional representations that bear little relation to the clothes of actual pirates.
Fictional Representations and the Image of the Pirate
Most people’s image of a pirate is rooted in representations of pirates from the golden age of piracy. This was an era from the mid-17th to the mid-18th centuries when there was a dramatic rise in the number of sailors who took to the profession.
Crucially, in this early modern world, pirates were not seen in a negative light (the way the Vikings had been in earlier centuries, for example). Instead, they were romanticized as rebels and anti-authoritarian heroes. 
In later centuries, this image of the pirate as a cheeky folk hero has only been further solidified. As the protagonist of numerous romances and adventure stories, pirates have made their way into the dreams of young boys and girls.
However, in telling their stories, authors often had little historical information to go by. Often, they made up for the lack of information by relying on their inventive abilities.
The nature of these genres and their mass and, frequently, young audience bases meant that pirates became more charming and flamboyant over time.
Some of the most iconic items of pirate costumes are associated strongly with representations in books and movies. These include Long John Silver’s wooden leg in Robert Louis Stevenson’s Treasure Island.
But, while pirates may have had amputated limbs from working under hazardous conditions, there are no known instances of a pirate with a hook for an arm, as Captain Hook does in J.M. Barrie’s Peter Pan.
Similarly, eyepatches, bandanas, and earrings – other pieces of costume closely tied to pirates in the popular imagination – may have been adapted from depictions of Spanish bandits by an illustrator of children’s stories. 
With pirates, much of what we think we know is of dubious historical provenance.