How to Dress Like a Pirate

Portraying a pirate convincingly requires the right combination of clothing, makeup, and accessories, as well as having the right demeanor. Whether you're becoming a pirate for Halloween, a costume party, a play, or just for fun, dressing like a pirate can be done easily with clothes you likely already have, or you can shop for new ones to get a specific look. After you've done this, you'll just have to practice your "arrrrrgh, matey" and walk the plank!

Method 1

Method 1 of 2:

Look Like a Pirate

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1
Have the right face. If you want to pull off the pirate look, you'll need to be convincing from the neck up. The right clothes won't take you very far if you don't have the face and head of a pirate. Here's what you do:
- Have a nice tan, or apply makeup that is a few shades darker than your skin to give yourself a tanned look. You spend all of your time on the deck of a ship, so it's only natural that you would have a sun-kissed complexion.
- Have rosy cheeks. Both male and female pirates are busy sword fighting, sparring, and running around the deck, so they should have a flushed look to their cheeks. Gently apply some blush for the look you want.
- Have smoky eyes. All pirates should have eyes that are lined in dark eyeliner to create a smoky effect. Both genders should also apply dark eyeshadow to emphasize their look. An eye patch can also be great for this costume.
- Pirate hair should be wavy and should look natural, like it dried in the sun.
2
Wear the right clothes. Having appropriate attire will help you achieve the pirate look you are going for. Not only do you need the face of a true pirate, but you should wear the shirt and pants of a true sea dog to capture the essence of a pirate. Here's what you do:
- Whatever you wear, remember that you've spent many years aboard a ship and don't have time to buy new clothes, and that you do your laundry in salty water aboard a ship. Therefore, your clothes should have a faded, lived-in look. The more patches and rips in your outfit, the better.
- Both men and women can wear loose white poofy shirts that they can tuck into their pants. They can have untied drawstrings hanging from their collar. Men should reveal their chest hair, and lady pirates can show a little bit of cleavage. In a pinch, you can also make a modernized take with a white tank top.
- You can layer a red or black jacket over the white top. Pirates can get cold at night on the windy seas.
- Men should wear tight leather pants, or ripped black jeans. Women can also wear tight leather pants, or a poofy red skirt and black laced leggings with an interesting pattern. The leggings can have rips in them too.
- A great idea is to use rolled up pants with elastic below the knees, for a variant puffed up look.
- For shoes, wear either pointy black boots, ragged brown sandals, or even bare feet, if it's appropriate.
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3
Have the right props and accessories. The right props and accessories can help accentuate your outfit and show that you really put a lot of thought into your pirate look. You don't have to be weighed down by too many items, but a few key additions will help complete your ensemble. Here are some things to consider:
- A pirate hat (also known as a tricorn hat) is a must. This three-cornered hat will add mystique to your look.
- A leather belt. Bonus points if you have a place to store your sword or if you have layers of different belts.
- A plastic sword. A plastic gold or silver sword that is not dangerous should be tucked into your belt. Be careful with this prop and make sure everyone around you knows it's not real before you whip it out.
- A parrot to keep on your shoulder. This will really impress the public. A fake parrot is best.
- A bag of gold doubloons to sling over your shoulder. It should make noise as you clink the coins together, and they can occasionally spill out. This will show that you've had a successful time pillaging and plundering out on the sea.
- An empty bottle of rum. Pirates love their rum, so you should bring out a bottle of rum filled with a non-alcoholic beverage such as root beer that looks like rum so you can take swigs from it periodically. If you're at a party or another place where it's appropriate to drink, and you're of legal age, drink from a real bottle of rum.
- A few key temporary tattoos. A tattoo of a skull and crossbones or of an anchor placed on your bicep, neck, or forearm will help complete your look.
- The right jewelry. A true pirate should wear a thick gold necklace and sliver and gold loop earrings. If you're a man and don't have your ears pierced, clip-ons will do.

Method 2

Method 2 of 2:

Have the Attitude of a Pirate

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1
Have the swagger of a true pirate. To pull off your look, you have to be completely confident. If you act like your look is perfectly natural instead of being self-conscious, then people will take you seriously and will be convinced you're a real pirate. Here's what to do:
- Don't act like you're wearing a costume. When people compliment you on your outfit, look confused and brush them off.
- Walk around with confidence. Strut your stuff, walk with confident strides, and pose with your hands on your hips. Don't cower in a corner with your hands folded, because that's not what a real pirate will do.
- Wherever you are, march around looking in all directions, as if you're preparing for a sword fight that you'll win any minute.
2
Act like a pirate. To pull off your pirate look, you'll have to have the attitude of a true pirate as well. You can't slip up and talk like a regular person, and should remember to be capturing the attitude of a pirate at all times. Here's how:
- Be slightly aggressive at all times. Scowl, growl, and be surly.
- Slur your words. Pirates are tipsy, so don't forget to slur everything you say, and never talk too quickly.
- Refer to yourself as "me." As in, "Me needs another swig of this here rum."
- Say "yer" or "ye" instead of "your." As in, "Ye need to get yeself together, ye mangy rat."
- The occasional "Ahoy!" or "Blimey!" will go a long way.

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What shoes can I wear to look like a pirate?
Alina Bokovikova
Costume Designer
Alina Bokovikova is a Costume Designer from California. With over 15 years of experience, she specializes in designing costumes for stage productions. Alina earned an MFA in Costume Design from the University of California, San Diego and her Master of Education from the Novosibirsk Pedagogical University. She’s won two Outstanding Costume Design awards and her costumes have been displayed in Moscow, Prague, and San Jose, California.
Alina Bokovikova
Costume Designer
Expert Answer
Boots are great! A pair of black rubber boots would work really well. For a more feminine look, cargo boots would be best, but even a pair of Doc Martens could work, too. You could also pair some leather boots with some knee-high socks.
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Where were the first pirates found?
Garrett
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Pirates were never really "found", but some of the earliest documents of traditional buccaneer pirates originated in the 17th century. Raids by thieves on ocean waters go back centuries before that.
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Should women have hook hands and peg legs?
Community Answer
Yes, they can. Hooks and peg legs aren't just for men.
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Hanging out with a crew of like-minded pirates will help you achieve a more believable look.
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Don't forget to mention that you just got over a bout of scurvy every once in a while.
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