The Dope-Ass History Of Lady Pirates

China’s Madame Ching commanded the largest fleet of any pirate — male or female — in history. ⚔

While Halloween costume fads come and go based on what makes the news and the box office each year, the pirate remains a perennial favorite, especially after the blockbuster success of Disney’s “Pirates of the Caribbean” films. In fact, among over-35s who’ll rock the party this year, the pirate costume is the most popular after the witch, says the National Retail Federation.

With its frills and sashes, the androgynous getup is pleasingly non-gender specific. (As we’ll see, this is actually kind of historically accurate.) This year, if you plan to dress as a lady pirate, we’ve got some options for you, along with a wicked dose of feminist pirate history. Yar! Avast, matey! And away we go…

Sayyida al-Hurra

The governor of the Moroccan city of Tétouan on the northern tip of Africa, Sayyida al-Hurra (c. 1492–1552) is often included in lists of lady pirates, but historians aren’t sure if that’s accurate. Her name means “noble lady,” and has referred to many other prominent women in the Muslim world. What we do know is that Moroccans back then were viciously fighting off the Portuguese, who had strangled their ancient trade routes and sacked and occupied their cities. That resistance included the use of Andalusian privateers, who raided Portuguese shipping lanes in the Western Mediterranean. Al-Hurra may well have approved of these tactics.

Tétouan was the only port in Morocco outside of Portuguese control, possibly because al-Hurra made Ottoman Turkish corsairs, or pirates, welcome there. All this probably explains why she’s been called a Pirate Queen. In any case, as a noblewoman, it’s a safe bet the girl could dress. To channel al-Hurra this All Hallow’s Eve, we suggest long, flowing robes, a jeweled headband and, of course, a sword.

Anne Bonny & Mary Read

Most of our sartorial ideas about pirates come from the Golden Age of Piracy, from 1650 to 1725 in the Americas. It was the time of Blackbeard and “Calico” Jack Rackam (fashionably depicted by Johnny Depp in “Pirates of the Caribbean”) who created the skull and crossbones flag, the Jolly Roger. Charles Johnson writes of two female pirates from this time. Historians aren’t sure his accounts are accurate, but their lives—whether totally factual or embellished—make for some thrilling storytelling. Anne Bonny was born in Ireland in 1700 and moved to Charleston, South Carolina as a young girl. A definite libertine, Anne became enchanted with a pirate named James Bonny, enraging her father, who wanted her to marry a nice medical student. (Typical!) Anne and John eloped to Nassau in the Bahamas, a haven for some 1,500 pirates. Then John tired of the piratical life. A bored Anne haunted local bars, where she met the flamboyant Calico Jack Rackam. She eloped again, and embarked upon a life of piracy, disguised as a man.

Eventually Anne, whom Johnson delicately described as “not altogether so reserved in Point of Chastity,” became enchanted with a young sailor on Jack’s crew and declared her love for him. To her surprise, the sailor revealed himself to be a woman! The woman was Mary Read. When a super-jealous Jack threatened to slit her throat, she revealed her secret. Jack agreed to hide the truth of their gender from the crew.

Mary eventually fell in love with a Dutch sailor. When an argument broke out between him and a veteran pirate, a duel was called. Her lover not being much of a fighter, Mary knew he would lose, so she picked a fight with the old pirate herself. With her naval training and natural ferocity, she was able to kill the buccaneer and save her man. She decided to drop her disguise, since she’d proven herself in combat. Anne did, as well, and the two fought openly as women from that day forth. Fed up with Calico Jack’s piracy, the governor of Jamaica sent a privateer to capture them in 1720. When the attack came, many of the pirates were passed out drunk on the deck, celebrating after looting a ship. Always “forward and Couragious,” Anne immediately skewered two privateers as they attempted to board. Infuriated to see Jack and other men scampering belowdecks to hide, she exclaimed,

“Dogs! If instead of these weaklings I only had some women with me…come up and fight like Men.”

Anne and Mary alone fought the privateers, but they were outnumbered. The whole crew was captured and stood trial. Calico Jack was hanged the day after the trial. Visiting him beforehand, Anne told him, “If he had fought like a Man, he need not have been hang’d like a Dog.” Mary died of fever in prison while lawyers reviewed her case. Anne was spared because she was pregnant. She gave birth in prison, and historians don’t know what happened to her after that. If you’re dressing up as Anne or Mary, you have options! Go for the androgynous look of their early, disguised days, or the more relaxed look of their “out” period. And there’s a third option: the sexy, swashbuckling style in which artists of the day depicted the two in accounts of their exploits, sold to horny Dutch dudes.

Anne Mills

Another pirate who was clearly as tough as any man, Anne Mills disguised herself as a man and signed as a common sailor on the English frigate Maidstone around 1740, during the War of Austrian Succession, fighting against the French. Boy, did she hate the French. After defeating one enemy in hand-to-hand combat, she “cut off the head of her opponent, as a trophy of victory.” That’s how history will remember her, though she doesn’t really look like she’s attempting a disguise in this famous engraving of her, which shows her wearing a man’s tunic — over a skirt. Oh, well, it’s the severed head that’s really the focal point of this costume choice, anyway.

Ching Shih

A vast fleet of 1,800 ships and 65,000 pirates terrorized China’s sea and rivers under the command of buccaneer king Ching I and his wife, Ching Shih. Madame Ching had been instrumental in building this fleet: In China female pirates fought alongside the men and even commanded ships. When Ching I died in 1807, his widow took command of the fleet, eventually expanding it to 2,000 boats. It was the largest pirate fleet of any pirate — male or female — in history. Madame Ching enforced a strict code of conduct among her crews, forbidding pirates from taking from the communal loot pile, torturing captured women and children—or committing rape. “No pirate may take a woman without her consent, nor wed her without permission of his chief officer. To do so means instant death.”

The Chinese imperial navy tried to eradicate Madame Ching’s fleet, but had so little success, they eventually granted her a pardon around 1810, even giving her pirates farmland to settle. It’s unclear what became of Madame Ching. Some say she ran a gambling house or became a smuggler — or married a governor and became a fine lady. Madame Ching is revered by the Chinese as the most successful pirate ever. It’s unclear exactly what clothes she wore, but she’s shown dressed as a woman in both Chinese and European accounts. Given that women fought alongside men, trick-or-treating as Madame Ching gives you the opportunity to go full-on femme with your costume. So if you’re planning to go as a lady pirate this Halloween, arm yourself with sword, hook — and a bit of history.