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Posted on Jan 9, 2019

A History of Pirates and Pirate Costumes

A History of Pirates and Pirate Costumes

Pirates are one of our favorite costume themes of all time, and not just for Halloween. Gasparilla and other pirate festivals are tons of fun year-round, they work at Renaissance faires, and they’re a necessity for Talk Like a Pirate Day. So, here’s our comprehensive guide to everything related to pirates and pirate costumes. To learn more about pirate costumes, we need to talk about pirates themselves, and we’ll be discussing both here.

The Golden Age of Piracy

Capture-of-BlackbeardCapture of the Pirate, Blackbeard, 1718; Jean Leon Gerome Ferris

Pirates and records of pirates have been around almost as long as there have been records of ships and sailing. As ancient Mediterranean civilizations began to flourish in the 11th and 12th Centuries BCE, bands of organized brigands were starting to appear, originating around the Aegean Sea and reaching as far as Egypt.

When most people think of pirate costumes and swashbucklers on the seven seas, though, they’re typically thinking about the period known as the Golden Age of Piracy. Lasting roughly from the middle 1600s to the middle 1700s, the Golden Age saw a huge influx in pirate activity in the Caribbean region, in Northern Europe, and along the African West Coast. This is also the time period in which the majority of popular pirate stories are set, from classic novels such as Robert Louis Stevenson’s Treasure Island to modern movies like the Pirates of the Caribbean series and video games like Assassin’s Creed IV.

So, when we’re discussing real, authentic pirate costumes, this is the era we’re talking about. The Golden Age itself can be divided further into three distinct periods, each with its own significant contributions to pirate lore and legend.

The Age of the Buccaneers: 1650s to 1680s

With multiple major wars in Europe all coming to an end around the same time, like the Thirty Years’ War, the Eighty Years’ War, and the Wars of the Three Kingdoms, countries were able to devote more resources towards expanding their empires. Naturally, as the opportunities for travel and trade across the Atlantic grew, so did the opportunities for maritime plunder and pillage.

Buccaneers were a group of mostly French sailors who had settled around Hispaniola (and not Tampa Bay) in the 1630s. When the English took Jamaica from Spain in 1655, governors began granting buccaneers letters of marque – contracts that turned the amateur bandits into commissioned, professional privateers. The job of a privateer is to capture the ships and supplies of his master’s enemies. Really, it’s straight-up piracy, as we think of the term, but “legal.” As one might imagine, plenty of privateers abused their job title all over the place.

As the number of privateering contracts grew in the Caribbean region, locales like Tortuga and Port Royal became hotspots of activity for French and English pirates, alike.

The Age of the Pirate Round: 1690s to 1700s

The Pirate Round refers to a trans-Atlantic trade route that helped the Golden Age of Piracy spread outside the Caribbean. Beginning in Caribbean ports like Nassau as well as other cities on the Atlantic Ocean as far north as New York, ships would sail south, around the Cape of Good Hope, with intended destinations of India and the Arabian Peninsula. The East India Company and other large traders used the route too, which made it a prime target for pirates.

Pirate booty was also starting to dry up in the Caribbean, anyways. New laws and taxation was making trade (and therefore, piracy) less profitable in the region, and Asian goods like silk were the new hot commodities. So, now-famous pirates like Henry Every and William Kidd started setting their sights on the less-naval-protected Indian Ocean.

We also have the Pirate Round and similar routes to thank for the dubious stereotype of modern-day Somalian pirates. They’re not nearly as prevalent anymore, but they’re there. (Captain Phillips was based on a true story, you know.)

The Age of Spanish Succession: 1700s to 1710s and Beyond

With the end of the War of the Spanish Succession and Queen Anne’s War, a great number of military sailors and privateers suddenly found themselves out of work. At the same time, both cross-Atlantic trade between Europe and the American colonies and triangular trade were booming. Not surprisingly, many of these former-navy, experienced sailors took this as an opportunity to turn to piracy.

This era also saw the emergence of who are likely the two most famous female pirates in history, Anne Bonny and Mary Read. Anne Bonny was the lover of the pirate Calico Jack, perhaps better known as the designer of the skull and crossbones Jolly Roger pirate flag. Mary Read joined their crew after being aboard a ship that Calico Jack attacked.

By the 1750s or so, the Golden Age of Piracy was quickly dying off, with only sporadic outbursts of pirate activity through the end of the century.

Historical Pirate Costumes

blackbeard-pirate-woodcutBlackbeard the Pirate, Benjamin Cole

Pirate costumes are always a great choice for Halloween, but are they really similar to how actual pirates used to dress themselves?

Pirate Clothes

Early accounts of maritime fashion (from the 11th Century and earlier) don’t describe anything more interesting than the ordinary menswear of the time, which included simple shirts, pants, and shoes. Many early sailors would dye their clothes blue to act as camouflage from enemy archers.

Starting in the 16th Century, and onward into the Golden Age of Piracy, ships would typically stock what was called a “slop chest,” which held uniform supplies of basic clothing for all the men aboard. The word “slops” or “sloppes” itself referred the baggy style of garments.

Typical pirate clothes were totally made for function over fashion, but that’s not to say they were totally austere. Many pirates were actually quite good at sewing, a skill learned from mending sails and such. So, while we doubt there were many pirate sewing circle tea parties happening on the high seas, it wouldn’t have been unusual for a sailor or pirate to customize or embellish his own garb.

We mentioned Anne Bonny and Mary Read as being the most famous female pirates ever, but female pirate costumes aren’t exactly a historical accuracy – what’s more than likely is that they wore what the men did. It’s a far cry from the sexy pirate costume you or someone you know might have worn a Halloween or two ago, and it’s definitely not even close to Keira Knightley’s gorgeously ornate and perfectly tailored black pirate gown battle dress ensemble from Pirates of Caribbean: At World’s End. In other words, not only does Elizabeth Swann pull that thing out of nowhere in the movie, but the costume designers pulled it out of nowhere, too.

Pirate Hats

Yes, pirate hats get their own section. Why? Bar none, they must be the most stereotypically recognizable pirate accessory of all time.

Some of the earliest hats associated with sailors in Europe, and therefore what an early-age pirate might have worn didn’t look anything like pirate hats at all, though. They were all styles of skull caps – very dissimilar to what you would imagine pairing with a pirate costume today. Early leather caps with chin straps were sturdy, warm, and wouldn’t blow away in the wind, which is really what a sailor on the high seas would be looking for.

By the later 16th Century, knitted hats of wool were becoming more popular than their leather counterparts. “Monmouth caps” were actually pretty close in appearance to winter knitted hats that are still worn today, and had the same basic shape of the stereotypical sailor hat. John Smith – yes, that John Smith – noted these hats as essential equipment for those wishing to sail to the New World.

Up until this point, pirate hats were all pretty simple, but the cliché pirate costume styles with which we’re all familiar were starting to come into play by the early to mid-17th Century. One of the biggest new hat styles of the time was the Cavalier Hat. These are the large, felted, wide-brimmed hats adorned with huge feathers, usually the plume of an ostrich.

In other words, this is when the Captain Hook pirate hat style started to become popular. The look was inspired by the Swedish military during the Thirty Years War (which ended in 1648, right when the Golden Age of Piracy was starting) and was seen as look of toughness and bravado. Naturally, every sailor or sea merchant in Europe wanted the same level of swag, and the hat was the way to get it. Other ornamentation might have included bands of gems and jewels sewn into place.

If you’ll recall, the early styles of popular sailing hats in Europe were tailored to be close to the head, so that they wouldn’t blow away in the wind. As it turns out, a lot of seamen were totally shocked that their spiffy new Cavalier hats were blowing away in the wind. It does sound silly and over-simplistic, but this was one of the biggest reasons why the standard issue three-cornered pirate hat started appearing in the 1650s. The first ones were, quite literally, older styles of wide hats with the brim pinned up and out of the way.

Pirate Accessories

It’s a common trope that pirates might wear bandannas around their heads, but there’s not a lot of historical evidence to suggest that was a popular style for sailors in the 16th and 17th Centuries. A modern idea about pirate costumes that does have a grain of truth to it, though, is the pirate eye patch. The Arabian pirate Rahmah ibn Jabir al-Jalahimah famously wore one after losing his eye in a battle. Along with the notion that keeping one eye in the dark will let it adjust more easily at night, this is where the “pirates wear eye patches” stereotype really came from, though it was further popularized by Robert Louis Stevenson’s Treasure Island in 1883.

As for your standard issue, knee-high black pirate boots, boots in general were typically reserved for captains, first mates, and the like. Many pirates and sailors during the 17th and 18th Centuries would often be barefoot while on the ship, allowing for greater agility and better grip when working in the ropes and riggings above.

Pirate Costume Ideas

So, now that you know everything there is to know about real pirate costumes, it’s time to get the look yourself. Whether you’re prepping for a pirate festival like Gasparilla, or you’re way into Talk Like a Pirate Day, or you’re just heading off to a costume party, a good pirate costume is easy to accomplish and can get a lot of attention.

Pirate Costumes for Adults


It’s no secret that Captain Jack Sparrow is one of the all-time popular pirate costumes for men. Pirates of the Caribbean costumes have been huge ever since Curse of the Black Pearl came out in 2003, and with the fifth film in the series, Dead Men Tell No Tales, released in 2017, it’s safe to assume that they’re not going anywhere anytime soon.

So, if you’re a guy looking to get that swashbuckler swag, this Captain Jack Sparrow costume is a great place to start. With included coat, belts, and – naturally – Jack’s signature hat, it’s the perfect mens pirate costume. If you’re a gamer at heart, though, then Edward Kenway from Assassin’s Creed IV: Black Flag might be more your style. There are always more classic options to explore too, like this red and black cutthroat pirate costume, or this simple white pirate shirt (that one doubles as Seinfeld cosplay).

For the ladies, sexy pirate costume ideas are a top theme every Halloween. Anne Bonny and Mary Read dressed like dudes, but that doesn’t mean you have to. With a sexy pirate wench costume, it’s easy to take control of the high seas. Of course, if you’d prefer a women’s pirate costume that’s little bit more – ahem – battle ready, then this rustic pirate costume for women is the perfect fit. Its faux leather corset and ruffled blouse lend plenty of feminine flair to a look that’s still all about kicking butt and claiming booty.

Pirate Costumes for Kids

Just as they are with mom and dad, Pirates of the Caribbean costumes for kids are hugely popular. For boys though, Jake and the Never Land Pirates costumes are just as big, if not bigger. What little boy wouldn’t love a real-life adventure on the high seas, complete with hidden treasure? Pirate costumes can make it happen, even if it is just imaginative play.

Girl pirate costumes are constantly growing in popularity, too – anything the boys can do, they can do better! They’re a great mix of glam and gangplank as well. Whoever said pirates couldn’t be pretty in pink? Angelica from On Stranger Tides and plenty of other customizable costume designs are ready to set sail.

A kids pirate costume or two can also really dress up a birthday part. Visit the Birthday Express blog to get some amazing pirate birthday party ideas for kids. There’s no age limit, either: even toddler pirate costumes can make a first birthday extra special!

DIY Pirate Costumes


If you need truly, absolutely last-minute pirate costume ideas, there are plenty of things you can do to turn yourself into a procrastinating pirate. Here are some quick ideas for an easy pirate costume that you can probably put together with items you might even already have:

  • Any piece of black felt or construction paper can be made into a quickie eye patch. Cut it down to size, then attach a length of elastic or string to secure it to your head.
  • A folded red bandanna, tied around the head, will do just fine in place of a real pirate hat.
  • A scrap of black or red fabric can be used as a quick waist sash or pirate belt.
  • Turn an old T-shirt into a pirate shirt: distress the sleeves and bottom of the shirt with some holes and tears for that sea-weathered look. Cut off the neckline and collar too, for a loose fit.
  • Stripes are a pirate-y pattern: if you own striped pants, you’re halfway there! Otherwise, thrift stores are the way to go.
  • While you’re there, raid the jewelry section for hoop earrings (you can paint them gold if necessary) and other hidden pirate treasure.
  • To make your own pirate sword, cut the shape from a piece of cardboard. Paint with silver paint for a metallic finish.

Pirate Festivals

If you’re chomping at the bit for a chance to channel your inner swashbuckler, then you need to check out a pirate festival or two! If you’ve never been to one, think along the lines of a Renaissance faire… but with pirates. Costumed actors, parades, re-enacted sea battles, dancing, drinks (read: rum), and music are your typical pirate festival cornerstones, and dressing up like a pirate yourself only adds to the fun.

Tons of these events are going on all the time. (If you live on the Atlantic coast, there’s probably one happening near you within the month.) Here’s some history on just a few of the best and biggest pirate festivals in the United States.

Gasparilla Pirate Festival

The Gasparilla Pirate Festival is perhaps the best-known and highest-attended pirate festival in the United Sates – more than 300,000 people descend on the Tampa area every year to partake. In the past, it’s been a bonafide holiday, complete with school and business closings, with the main parade and festival itself taking place on the second Monday of February. This year marks the 10-year anniversary of the event’s move to the last weekend in January, which was done in 2005 to increase participation levels even further.

So, between Gasaparilla and the Tampa Bay Buccaneers, why does Tampa seem to have such an obsession with pirates? The answer lies with the local legend of José Gaspar, for whom the festival is named.

Jose Gaspar

Historical records about Gaspar are inconclusive at best (and non-existent at worst), but according to the stories, he and his crew plundered and pillaged Florida during the late 1700s, amassing hordes of treasure and riches. The treasure was said to have been buried on Gasparilla Island, never to be found again. It’s an interesting story for sure, but it’s likely entirely fictional – the earliest written record of Gaspar comes from a promotional brochure published by the Charlotte Harbor and Northern Railroad Company. The railroad just so happened to terminate at a hotel on Gasparilla Island, and the legend was born to spur public interest.

gasparilla pirate ship floatA pirate ship parade float, in preparation for Gasparilla | via Wikimedia Commons

As for the pirate festival itself, Gaspar and the pirate theme were brought up by the Tampa council in charge of public events. They were looking for a way to make their May Day party more like New Orleans’ Mardi Gras, and decided that pirates were the way to go. Tampa’s first Gasparilla, in 1904, saw a band of pirates invade the city streets on horseback. In 2014, full fleets of ships and decorated floats took over the town entirely.

In other words, an advertising campaign for a hotel in the early 1900s has turned into a multimillion dollar-generating annual extravaganza and cultural staple. Now that is some good marketing.

Billy Bowlegs Pirate Festival

Much like Gasparilla, Billy Bowlegs is a pirate festival inspired by a local legend and folktale hero. The difference is that William Augustus Bowles was definitely and verifiably a real person. As a member of the British Army, he was placed in charge of the crown’s interests in the Creek and Cherokee Nations after the American Revolution. Shortly after, he joined forces with the Florida Seminoles to establish his own country and declare war on Spain, in a classic historical case of things escalating quickly.

William Bowles

Bowles was captured by the Spanish and brought abroad, only to escape from imprisonment, commandeer a ship (likely in true Jack Sparrow style), and return to the Americas. Now a full-fledged pirate, his legend was cemented in history.

After having began in the 1950s as a show dedicating to boating, waterskiing, and other seaside sports, the Billy Bowlegs Pirate Festival slowly transitioned into the mini Mardi Gras festival that it is today.  It’s always on the first weekend in June – which is plenty of a buffer from Gasparilla if you ever want to attend both.

The Hampton Blackbeard Pirate Festival

If someone asked you to think of any pirate name off the top of your head – and not a fictional one – you’d probably think of Blackbeard. Born Edward Teach in Bristol, England, Blackbeard was quite possibly the most renowned pirate of his day and is the iconic modern-day image of the classic pirate.

blackbeard maynardBlackbeard Boarding Maynard’s Ships, George Edmund Varian

At the helm of the Queen Anne’s Revenge, much of Blackbeards domain, in his final years, areas around the Carolinas and Chesapeake Bay, which explains the origin story of this pirate festival in Hampton, Virginia. The event’s history on its official website includes embellished tales of Blackbeard himself actually hosting the inaugural installment of the festival in 1718, which culminated in his ambush by and final battle with the Royal Navy and Lt. Robert Maynard.

As such, the actual event brings that narrative to life, with Blackbeard and other pirate reenactors commanding fleets of ships and leading the festivities. Dozens of ships take to Hampton Harbor for the festival’s main event – a full-scale, simulated battle at sea, broadsides and all. When Blackbeard falls and Maynard is victorious, every guest in attendance gets a piece of the pirate’s legendary treasure.

Have we inspired you to swash some buckles and channel your inner pirate at the next costume party? If you liked this blog and want to see more like it, then let us know! Follow us on Facebook and Twitter @BuyCostumes to share your thoughts, or send us a quick email. Be sure to check out our Pinterest boards for more awesome costume ideas, too.

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