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The Very Basics
Decide if you want to be a man or a woman. You'll probably want to be a female pirate if you are a female and vice versa, but it's up to you. Many female pirate depictions are quite inappropriate -- if you're not looking for that, consider just girling up a male pirate's outfit.
Find a pirate image. This can help to guide your pirate costume crafting, but it's certainly not essential. It's likely to be useful where there is something unusual or fascinating about the costume of a particular pirate that you'd like to emulate.
Creating the Pirate Top: With a T-Shirt
Select a large white t-shirt that you're willing to change. For pirate crew, your top doesn't need to be as fancy as that which would be worn by the pirate captain or long-term senior pirate crew. A t-shirt will serve adequately. A larger shirt is best to give the idea of rugged sloppiness, which all good pirates attempt to get across. You could instead use a tank top or a white button-up shirt as a top.
Start sculpting. You've been at sea for months. Though you don't want to pretend you have scurvy, make it seem you're a little worse for the wear. Cut areas of the t-shirt to give an impression of ruggedness: Cut off the ends of the sleeves in a jagged fashion. Cut the bottom of the t-shirt off. Pirates don't need hems. Cut off the neckline of the t-shirt. $10 says Hanes was not around in the era of your pirate.
Paint blue stripes across the shirt using fabric paint. Also paint lines around the sleeves. These don't need to be perfect––the more homemade they look, the better. Allow the paint to dry, then flip the t-shirt over and paint the back the same way.
Creating the Pirate Top: With A Shirt
Find a suitable shirt. If you'd rather wear a shirt than a t-shirt, that's fine too, especially if you're trying to be a pirate captain. A big, billowy white shirt is ideal. Try to locate one which has flowing sleeves rather than tight ones. For women, choose a man's shirt as it will be bigger and more likely to billow. For men, avoid anything that's too tight or too short.
Lose the stiff collar. Pirates don't wear stiff business collars. Away with it (give it the plank!) by snipping it off and restoring a ruffle or similar soft collar instead. If you hate sewing, you can probably get away with using fabric glue to attach a ruffle but ensure that the area that has been cut won't fray. If possible, just try tucking in your ruffle to your neckline. The volume of the ruffle will cover up any self-improvements you've made to your shirt.
Embellish a little. Since you're wearing a decent shirt, it's more about upgrading than turning it to tatters. Consider some of the following embellishments: Fancy buttons for both the middle and cuffs A golden or silver chain toggle for the collar area Ruffles! Ay, matey. Ruffles can be added almost anywhere on the shirt ––around the cuffs, around the collar, down the button line, etc.
Creating the Pants And Vest
Choose dark colored pants for a conservative or simple look. Let the rest of the costume do the talking. In days of yore, no pirate was donning floral-printed pants, so don't worry about your pants making a statement. If preferred, you can wear a long skirt with petticoats underneath. It's best if it billows out, to allow freedom of movement. This is something female pirates might like to wear in place of trousers.
Fix up an ordinary pair of pants. You could paint stripes on a plain pair of pants to give them more of a pirate vibe. Use fabric paint to paint on vertical stripes. The color can be matched to the pants or any other part of your pirate outfit. Perhaps you're part of a pirate gang? Roll up your pants legs to quickly turn them into a pair of pirate breeches. Another alternative is to wear pants but to wear a coat tailored to hug around the front with tails in the back like a full skirt. This would probably be something you need to sew yourself or have tailored, but it can be a nice combination of pants and dress.
Consider wearing a vest that opens at the front. Keep it plain and dark in color; if it fits the vibe of your pirate, leave it unbuttoned so that your shirt or t-shirt can be seen underneath. Classier pirates may want to be proper and stay buttoned-up. For a colder night, wear a very long, free flowing overcoat. It can have seen better days, provided it's not a tight fit. Search in thrift stores for such a coat. Again, it's best kept a darker color but can be colorful or patterned if you're a flamboyant pirate.
Making a Hat
Measure your head. Use this measurement to get the size of the pirate hat accurate. This is the part that tends to make the pirate costume. Fortunately, it's very easy to make a pirate's hat.
Draw a pirate's hat shape on a piece of paper. Use this as the template. If you're not confident in this, one can be found online. Place the template over lightweight card and trace around it. Do this twice, as you need two sides to the hat. Cut out the hat shape.
Stick or glue the hat together. Run glue or tape around the edges of the hat, leaving the base of the hat where your head goes in untouched. Let dry if using glue.
Paint the hat black. Go over with at least two coats and let dry. Then paint on the skull and crossbones design in white. Again, if you're not super artsy, print this off the internet and glue on. If you're using paint, this may take two coats; white over black at first is gray. Be patient -- your hat is one of the flashiest parts of your outfit -- put the time in to make it right.
Cut a band of card that fits your head precisely. Tape this together in a loop or circle. Slide this inside the hat and tape or glue to the hat. This will help to keep the hat shape open and keep it snugly on your head. If it's really windy out and you're forced to become an outdoor pirate, add elastic to keep the hat in place. Only do this as a last option though, as it can look a bit bulky and silly.
Adding Accessories
Wear a bandana around your neck. A bright red bandana around the neck will stand out and is something a pirate might well have worn. If you don't have one, make one! Cut a piece of red fabric in a large square shape. Fold the square into a triangle. Wrap around your neck. Tie the ends at the back of your neck and have the bandana tips pointed downward at the front of your neck.
Add a pirate belt. A belt around your shirt or t-shirt is a perfect pirate touch. You can either wear a very wide belt you've found in your own wardrobe or from the thrift store, or you can make a belt from fabric or card. Some pirates wore (or "wear" in the images on Google) a belt that more resembles a sash. If you have a black or red scarf, it can easily be turned into a pirate belt. Layer multiple belts for an eclectic pirate look.
Rock an eye patch. Eye patches can be purchased from costume stores or online, or you can make your own: Draw the shape of an eye patch on a piece of lightweight card. Cut out the patch. Paint the outer side black. Let dry. Pierce two holes into the top of the patch on either side of it. Thread in the ends of thin elastic and knot in place. Check that the length of elastic is just right for going around your head before cutting and knotting the final hole.
Wear old shoes or boots. Holes are perfectly fine provided you're not jumping puddles or snow. Add a buckle to improve the look of an old pair of boots, especially if you're a pirate captain The more worn, the better. Hit up your local thrift shops for shoes you will probably never wear again -- or at least not until next year.
Wear skulls or gold jewels like thick necklaces and earrings.
The Extras
Put some black makeup around your eyes. Just mascara and eyeshadow is good. If you're an evil pirate, this goes double. Shade your creases to give the look of added depth. You don't necessarily have to mirror Jack Sparrow, but his is certainly a good look.
Wear at least one earring. Wear a pair of big golden circle earrings if you are a woman; if you're male, one is good. Ear(s) not pierced? A lot of costume jewelry just snaps right on.
Wear a scarf around or in your hair if you are a woman. Fashion it like a headband -- a true pirate wears it like a sweatband. But yours can be much more fashionable and a little Bohemian.
Carry a cardboard cutlass or sword. Cut a cutlass or sword from cardboard. Paint the blade end silver and the handle end brown. You can slip this into your belt when not carrying it. Plastic ones are pretty cheap and abundant in costume or party shops, too. Your entertainment will be provided all night -- just be careful not to knock too many things over or poke someone in the eye.
Make a telescope. Use a tube from kitchen wrap or similar. Paint it black. Then attach a silver band about a quarter of a way from the top, to section it. Add another silver band to one end, which looks like the end the pirate looks through. You can attach this to your belt with a piece of elastic.
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