The Fashionable Swashbuckling Pirates


Do you ever fantasize about being one of the fashionable swashbuckling pirates that sailed the restless ocean? Perhaps you picture yourself as the hapless maiden in need of rescue. Either scenario calls to mind exciting adventure away from the hum-drum of everyday life. Just as with cosplay, the spirited privateer life has a great following. Costumes and role play come into the drama.

Many people get their ideas of buccaneer fashion from the ever-so-swashbuckling Jack Sparrow. The infamous character of Jack Sparrow was played by actor Johnny Depp in the Pirates of the Caribbean film series. Sparrow’s derring-dos take place during the so-called Golden Age when privateers took to the seas and displayed their courage. This was during the Age of Exploration, therefore many explored and plundered the deep blue seas.


There are not a lot of written or artistic accounts of buccaneers during this period, but we do have some ideas about what they wore. We even know that as early as 55 B.C., seamen were dressing in blue as camouflage against the waters of the ocean.


Fancy Dress on Rough Seas: Pirating in the Golden Age

By the time the Golden Age of piracy came around, roughly 1650-1730, the fashion for pirates had changed but was still practical. The deckhands spent their days barefoot so that they could easily grip the ropes with their bare feet. Their simple breeches were topped with linen shirts tied with a sash.

Those in charge on board ship, the Bosuns and quartermasters, typically wore the same along with waistcoats and hats. Of course a variety of assorted weapons were always a part of their attire. Shoes or sandals were worn by most to protect the feet from the harsh environment. Captains wore similar clothing along with plenty of flashy jewelry and accessories. There were some that were known to top off their looks with a jaunty pet, such as a parrot or a monkey.

Seamen also tended to have two styles of dress: rough and fancy. As the names suggest, a rough dress was for their work-a-day lives on board ship. Fancy dress was kept for more formal occasions and tended to include lace, brocade, fine metal buttons and jewelry.


Cabin Boys and Swabbies

In contrast, cabin boys, powder-monkeys, and swabbies likely wore simple breaches and blouses topped with a scarf or sash. These shipmates sometimes called swabbies, or sea dogs lived their life aboard ship surrounded by the turbulent waves. They had little need for fancy clothes.

Lady Buccaneers

Privateers or pirates were almost exclusively male. A few brave, bold women, however, were able to penetrate the old boy’s club of the high seas. Most of them would dress as men to keep their cover safe. Two of the best-known female buccaneers were Irish born Anne Bonny and cohort Mary Read. It was reported that Mary’s Mother passed her off as a boy when she was young. Desperately needing financial support from relatives, this ruse worked for a while. Anne Bonny, it seems simply enjoyed the unbridled lifestyle. Resisting a betrothal set up by her Father, Ann ran off to marry sailor John Bonny in 1718.

Mary Reed

For the protective cover, or just to fit in with the rowdy men, these two women held their own when drinking and swearing. They didn’t necessarily keep their sex a secret and typically wore men’s clothing. This was for both safety and convenience when traveling the high seas.

Grace O’Malley

Many pirates, both men, and women seem to have strayed from the rowdy island of Ireland. The infamous Grace O’Malley was known as a “brutal and thieving pirate controlling the coastlines through intimidation and plunder.


Pillaging and Plundering

Much like a modern-day thrift shop, a scurvy dog’s wardrobe consisted of a lot of cast-offs. Because of this, there was little to distinguish a pirate or buccaneer from a land-lubber. Since they worked with fishing nets and sails in need of constant repair, they were pretty handy with needles and thread. This made customization of the supplies at hand a breeze. To their artful clothing, they often added embroidery or decorations.

Baubles and Beads

When wealthy prisoners were captured, the booty that included fine fabrics and flashy baubles were treasured. With these hand-me-downs, their wardrobe could get a big upgrade. The laces, furs, precious gems, and metals were a celebration to behold.

Claiming their prize, Bellamy and his crew capture the Whydah without incident, scratch out an inventory, and divide the loot. “There was little bloodshed,” says expedition historian Kenneth J. Kinkor. “Sailors didn’t get paid enough to risk their lives against pirates.”


Certainly, the plunder was also just as likely to be sold off to the highest bidder to pay for ale or rum. The score of rum was a privateer’s best friend as many imbibed of liquor on a daily basis. This was partly due to the fear of contracting dysentery from the water. More likely though, it was the taste for liquor itself.


Because of the sumptuary laws of the time, not only the fabrics used but the colors worn were dictated by law. This was for class distinction, social level, and to identify the privilege allowed a person. Rebel pirates relished the ability to turn their nose up at authority by wearing colors and fabrics not allowed. This defiant attitude led to mismatched clothing galore. This motley display of clothing resulted in the term, motley crew.


Hats and Bragging Rights

No seaman’s outfit would be complete without the distinctive hat. Some pirates were known to even rank, or outrank, each other with their hat. The hats could be found in many shapes and sizes and were often worn with a scarf wrapped around the head. While the scarf was worn for fanfare and to hold the hat on in bad weather, it was useful for many other things as well.


Throughout the centuries, seafaring people would choose headgear wisely to protect their skin from the sun. The wide-brimmed cavalier hat was a long-time favorite as was the tricorn favored in Europe at the time. When the cavalier hat proved too cumbersome, Bucs would pin the bill to the brim. This handy hack served a double purpose, as they quickly learned. It helped divert sea spray from their faces and kept the rain off their heads.


Corsets and Pirate Wenches

All of the women, however, likely had one garment that no man needed: a stay or corset. Stays were designed to flatten the torso and would be used to maintain a long, lean look that could help lady buccaneers conceal their treasure chest a little more easily.

For women who were open about their sex, the corsets would be worn beneath their bodice. The overbust corset style would extend from just below the arms to the hips while the underbust style extends from the mid-ribs to the hips and lifts the breasts.

 Female Pirates Stand Proud

Then, as now, women would wear different clothes according to their station and job. Powerful captains, such as the female Chinese born Ching Shih, ruled the high seas commanding many ships and pirates alike.  Being a former prostitute herself, Ching likely dressed much like her male counterparts with rich brocades and velvet, precious metal buttons and buckles. The ostentatious tricorn hats that were worn at the time were often embellished with feathers, trims, and often a pretty brooch or two.


Yo Ho Ho, a Pirate’s Life for Me!

Today, the Pirate Code is defunct, but modern day fans of Grace O-Malley, the fictional Elizabeth Swann and others of their ilk can get their pirate-y fix by mixing and matching men’s and women’s clothing to achieve the perfect pirate costume.

Black and white are always classic background colors that pair well with more vivid jewel-toned colors such as velvety purple, lush crimson, emerald, and rich blue. These colors add vibrant depth and life to any costume and emphasize the outlaw nature of the high seas life.


A Hail to Pirate Wenches: To a pirate festival you go

The lure of rebellious pirate lore stays in the hearts of many modern day mutineers. Because of this, pirate festivals abound throughout the United States and abroad. Many boast several days of fun and debauchery. This allows the typically sedate personalities to become turncoats with fashionable dress and renegade behavior.

For the female pirates attending a big pirate festival or fancy dress bash, you can slip into some sexy fishnet tights to recall the netting on those big old ships. Next, add form-fitting leather or velvet breaches topped with a loose linen or silk blouse. A tightly laced corset with a full taffeta skirt offers a feminine alternative for those who want a sexier look. Many websites offer both custom and ready-made costumes for your escapade.

During the Golden Age, women would wear low heels. Efficiency isn’t necessarily the look of the day though as you won’t be climbing ropes or walking the plank. If you want to go sky high with your boots, now’s the time to do it!

Pirate Corsetry

No wench costume would be complete without some sexy, sultry corsetry. You can cinch the waist and add voluptuous curves for an eye-catching appeal. Because a well-made corset can be a major purchase, you might want to choose that first and build the rest of your pirate costume around it. is a good choice for your investment.

Add your sash, some big hoop earrings, a gold chain or two, gemstone rings, and your look will be complete. Top your hair with a fashionable swashbuckling pirate hat and you’re ready for adventure. Don’t forget to grab your dagger, cutlass or pistol as you board the ship.


For some exciting and entertaining pirate fun check out the upcoming festivals near you. You can’t go wrong with a day of fun and frolicking.

Finally, it’s time for some devil-may-care adventures. Just don’t forget to BYOR: Bring your own rum!



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