They Wore Their Wealth: What Real Pirates Wore, and Why the Captains Dressed Like Kings

Oil painting of pirate captain Bartholomew Roberts in a crimson and gold damask vest, red-feathered hat and gold chain with a diamond cross, while his crew in plain sailor clothes haul rope behind him, titled They Wore Their Wealth

At our anniversary party, we had a real pirate costumer in the lounge. Somewhere between the second cigar and the third story, he said something we can't stop thinking about: "A lot of pirates wore their wealth."

He's right. And the true story is even more fun than the costume shop version.

What did real pirates wear?

Most real pirates dressed like regular sailors. Think loose linen shirts, canvas or wool pants, and a knit cap or a scarf. That's about it.

No gold hoops. No fancy sashes. No matching outfits.

Plain clothes made sense. Decks were wet, work was hard, and nobody wanted to ruin their good shirt hauling rope. Plain clothes helped on land, too. If you were a pirate walking around a port town, the last thing you wanted was to stand out.

So who wore the treasure?

The captains did.

A pirate captain had a reputation to protect and a crew to impress. He also had a lot of stolen loot and nowhere to put it. There were no banks for pirates. Some of the treasure went into a sea chest. Some of it went right onto his back.

Meet the best-dressed pirate in history

His name was Bartholomew Roberts, and he may be the most successful pirate who ever lived. In about three years, he captured more than 400 ships. That's more than Blackbeard, more than Captain Kidd, more than just about anybody.

And he dressed like it.

In February 1722, a British Navy warship finally caught up with Roberts off the coast of West Africa. A pirate history book from 1724 tells us what he wore to that fight:

A rich crimson damask vest and matching pants
A red feather in his hat
A gold chain around his neck, with a diamond cross hanging from it
A sword in his hand
Two pairs of pistols slung over his shoulders

He wasn't hiding his money. He was wearing it into battle.

Roberts didn't survive the fight. But his crew kept a promise to him. They wrapped his body in the ship's sail, with his weapons and his fancy clothes, and gave him to the sea before the Navy could take him. The crimson, the gold and the diamond cross all went down together. He wore his wealth right to the very end.

Was "Calico Jack" a real pirate nickname?

Probably not, and we love that. John Rackham is famous today as "Calico Jack," supposedly for the calico shirts he wore. But historians say nobody called him that while he was alive. The nickname first shows up in a book years after he was hanged. Even funnier, calico was mostly used for women's dresses back then.

So "Calico Jack" was a costume somebody put on him after he was gone.

The pirates who dressed up for real

The best dress-up story belongs to Rackham's crew. Two of his pirates were women: Anne Bonny and Mary Read.

At their trial in Jamaica in 1720, a witness said they wore men's jackets, long pants and handkerchiefs tied around their heads, with a machete and a pistol in their hands. She still figured out they were women. The disguise wasn't perfect, but it was good enough to go pirating.

Dress like a captain this Halloween

Here's the good news for your Halloween pirate costume. If you pile on the gold and the feathers, you're not dressing like a real pirate deckhand. You're dressing like a real pirate captain. That's even better.

Our Halloween weekend at Pirate Cigar at Darkwater Alley in Pinellas Park starts with a costume party on Friday, October 30, and runs through Día de los Muertos on Sunday, November 1. Put on the feather. Wear the chain. Bring the loot if you've got it, and fake it if you don't.

The deckhands can come as they are. The captains will be dressed for the occasion.

Quick answers

What did pirates actually wear? Most pirates wore plain sailor clothes: linen shirts, canvas or wool pants and knit caps. Only some captains dressed in fancy clothes and jewelry.

Which pirate dressed the fanciest? Bartholomew Roberts. He went into his last battle in 1722 wearing a crimson vest and pants, a red feather, and a gold chain with a diamond cross.

Why did pirates wear their treasure? Pirates had no banks. Captains kept loot in sea chests or wore it to show off their success and keep their crew's respect.