Dressing up as a pirate for Halloween is lots of fun. There are a lot of variations you can go with, from pirate captain to a deckhand. Get a group of friends involved, and you can have a pirate crew! Here's how to to make a cool pirate costume.
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You can always buy a costume at any Halloween store, but that's too easy, and you'll look like a costume store pirate. It's fairly easy to make your own custom pirate look that you can supplement with accessories from the costume store if you want. The first step is to look online at some pirate pictures or some pirate costumes to get ideas. You can rent one of the Pirates of the Caribbean movies to get some good ideas also.
The heyday of the swashbuckling pirates was in the early to mid-1700's. Many pirates operated on their own, but many were sanctioned by different governments to raid each others' shipping. So you want to look like a gentleman from the 1700's. That means long hair, puffy clothes and weapons of the period. One of the first places to look for costume parts is at your local thrift store. Look for a white puffy collared shirt that opens to expose some chest. I found some nice ones in the women's section. If you look in a couple of stores, you should be able to find one. If not, you can substitute a loose-fitting white men's dress shirt.
While you are there, look in both the men's and women's sections for a basic black or dark-colored vest. This gives you that old-world look you need. Another item to look out for is some large belts with big buckles. You'll need a wide one with a big buckle around your waist, and one or two longer ones draped across your shoulders. Now you're stating to look like a pirate. If you can find a long red scarf while you are there, see if it fits around your waist as a sash. It goes under the belt as shown here. If you don't find one, go by a fabric store and get a couple of yards of nice red or wide-striped material that you can use. Get enough to also make a 30 inch square to use as a bandanna.
Pants and boots are next. For now, skip the blue jeans and go with something black, brown, or grey. Boots are hard to come up with. I recommend you buy some boot covers at a costume store, or you can wrap your legs over your pants to just below the knee with dark material. This simulates that you are wearing knee-length 1700s pants. For headgear, you need the bandanna whether you wear a hat or not. I was able to find a nice pirate hat at a Spirit Halloween store on discount last year.
Now just accessorize. You can get a cutlass or dagger at the dollar store or cheaply at a costume store. Wear a couple of costume jewelry rings and throw some gold chains around your neck. If you want to go with dreadlocks, you can clip some beads in with them ala Jack Sparrow. Grow a scruffy beard or pencil one on, along with a scar or two. Don't forget a big gold earring too.
An alternate approach is to go with a deckhand look. For this, you just need a bandanna, and go with a wide-striped rugby-type shirt instead of a gentleman's puffy shirt. Find some old brown or black pants at the thrift store and cut them off below the knee with a zigzag cut. Throw a belt over your shoulder and you are all set.
Either way, you can mix and match accessories, hang a pouch off your belt, go with an eyepatch or hook, or use whatever you find. You can be assured that you will be sporting a unique costume. Have fun and remember, to err is human, to arrr is pirate!