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The Princess Bride Dread Pirate Roberts Costume Guide

As you wish, here's THE twue-ly complete guide on the Princess Bride Dread Pirate Roberts costume. See how the young and naive farm boy, Westley, from the cult classic The Princess Bride movie dresses up in his rather alluring and suave Dread Pirate outfit.

Rather fittingly, this particular masked hero is also referred to through-out the tale as the Man in Black which, not surprisingly, is a really rather good description since he happens to be dressed in that dark color from top to toe.

This particular Westley Princess Bride costume has to be one of the suavest and coolest male dress ups ever with a genuine, swashbuckling protagonist to look like. Of course females can also look good dressed like this too.



Note: This post contains affiliate links for which I may be compensated.

A Complete Guide to The Man in Black, The Princess Bride Dread Pirate Roberts Costume

Westley with Rodent Costume Cosplay

Rodents of Unusual Size? I Don't Think They Exist! Love this take on a Westley Costume.

Image Credit: Cropped image shared by Clinton Steeds on Flickr with a CC License

I show you how to put together everything you need for a really convincing Dread Pirate Roberts costume. There's a list of items below if you're in a hurry and a detailed rundown of each item beneath.

The Items You Need for a Convincing Dread Pirate Roberts Costume

It's really quite easy to put this look together when you know just what you should be looking for.

I've made this part really easy by listing all the main items that you need to get hold of right from the start. Read below to get all the detail on perfecting the look.

1: Main Items You Need for a Convincing Dread Pirate Roberts Costume: The Black Headwrap

black bandana head wrap for pirate costumes

Get this Black Head Wrap from Amazon.com

UK Readers get a plain black bandana from Amazon.co.uk

Along with the terribly comfortable eyemask, the black bandana head wrap is a rather essential component to Westley's pirate outfit.

Wearing the head wrap is what keeps anyone, including his true love Buttercup, from recognizing him before they are meant to. It covers over his slightly long blond hair which is swept back into a tiny ponytail at the back.


Later on in the movie, Westley takes his head gear off. But then he's not really the Dread Pirate Roberts any more. Note to guys: the outfit looks so much more appealing with the head gear left on.

This one is made completely from cotton so it is not some horrible synthetic fabric that will scratch your head as you wear it. It also happens to be the one that many guys, and gals, playing this role choose to wear as part of their outfit.

2: The Terribly Comfortable Dread Pirate Roberts Mask

black eye mask for Halloween and mardi gras costumes

Buy a Black Costume Eye Mask from Amazon.com

UK Readers get a Black Eye Mask from Amazon.co.uk

Another key piece to the whole ensemble is the Terribly Comfortable simple black eye mask.

The eye wear pretty instantly turns you into what appears to be a real masked hero. Make sure you add one on to your shopping list. Westley says in The Princess Bride:

It's just they're terribly comfortable. I think everyone will be wearing them in future.

3: A Suitably Hero Like Dread Pirate Roberts Costume Shirt

black lace up pirate costume shirt

Get this Black Pirate Costume Shirt from Amazon.com

UK Readers get a Black Pirate Shirt from Amazon.co.uk

The type or style of shirt worn by this movie hero is a black pirate shirt, also known as a Renaissance style of shirt. Obviously it's solid black like all the other items that we're hunting for.

Pirate Buccaneer Renaissance Medieval Costume Shirt and belt BlackPirate Buccaneer Renaissance Medieval Costume Shirt and belt BlackZANheadgear Black Cotton Deluxe Head Wrap FlydannaZANheadgear Black Cotton Deluxe Head Wrap FlydannaBlack Men's Masquerade Mask Adult Halloween Costume AccessoryBlack Men's Masquerade Mask Adult Halloween Costume AccessoryMen shirt Pirate black Cotton Shirt - Steampunk Renaissance Fantasy Medieval Renaissance Costume CosplayMen shirt Pirate black Cotton Shirt - Steampunk Renaissance Fantasy Medieval Renaissance Costume Cosplay

 

But you also need to look for the key components of this shirt. It has a lace-up front and it also has long sleeves which are puffy.

The puffy sleeves are just right for billowing in the wind. The sleeves pull in tight around the wrist cuffs. This one has the right look but so would a Zorro style shirt as well.

4: Some Long Black Pants

You can get away with any long pair of black pants for this costume. You could wear black denim jeans or some reasonably tight fitting pants that hopefully show off your slim but muscular legs.

I've seen people wear ordinary denim jeans with a tight fit and these look fine too. But remember to be a true Dread Pirate, you really need to embrace the whole Man in Black thing!

5: Long, Black Pirate Style Boots

black pirate costume boot covers tops

Get these Black Boot Tops from Amazon.com

Westley wears long, almost knee-length, black pirate boots over some tight fitting pants or trousers.

The design of his boots are not too flamboyant because I think the costume designers really wanted the attention or focus of our eyes to be held firmly on his face and upper body. So they're actually fairly plain looking.


You can buy long boots for the purpose and Funtasma have some good looking costume ones. However a better buy may be to get some boot top covers like these ones shown here.

Boot top covers tend to be less expensive and can be worn over the top of some plain black shoes. It seems a really handy way to get the look of the footwear without the expense.

Westley Costume Princess Bride Weaponry Costume Accessories

DragonCon Parade Dread Pirate Roberts Westley The Princess Bride and Buttercup in Blue Dress Costumes

Image Credit: Shared by Jason Riedy on Flickr with a CC License

A key element to getting the exact right look of a Princess Bride Westley costume is his fencing sword. It's a particularly dashing part of the outfit and the thing that is really going to give you the edge when dressing as this character.

This one is a really nice looking rapier sword which could make for a good costume addition. Since this has a sharp point, it is not suitable for kids at all. If buying for kids, look for a plastic version which would makes a better and safer accessory for Halloween.

Musketeer rapier fencing sword great for cosplay

Get a Rapier Fencing Sword from Amazon.com

As a fan, you will really appreciate the actual replica of the movie sword (not pictured here) used by the character and the actor Cary Elwes. You can sometimes find it listed online for sale, try popular auction sites to search for it.

I'm a bit of a nut for movie swords and, if it wasn't for the high prices that they cost, I'd be proudly displaying them on the walls of my home. Instead I'll stick to drooling.

It's good to check out the full product images so you can see exactly what the sword looks like for your own reference if you are particularly keen to get the details correct.

Ace Martial Arts Supply Renaissance Rapier Fencing Sword with Swept Hilt GuardBladesUSA PK-6182 Universal Leather Sword Frog 8-Inch Overall

Lots of people do use rapier swords as cosplay accessories because of the styling and the fact that they look pretty good when sheathed safely from your belt.

You can then practice all The Princess Bride fencing moves, the Bonetti's Defense, Capa Ferro, Thibault and Agrippa, to your heart's content.

The Best Sword Fight in Movie History

Westley The Princess Bride Costume Accessory Sword Rapier Dread Pirate

Image Credit: Shared by Taavi Burns on Flickr with a CC License

The Cliffs of Insanity duel between Inigo and Westley has to rank up there as one of the best sword fights in a movie.

One of the most exciting parts in The Princess Bride and one I've seen over and over again is the fencing duel on the Cliffs of Insanity between the Spaniard, Inigo Montoya, and Westley as the Dread Pirate.

I'm sure that one scene has sparked off many an interest in Fencing and Sword Play. Part of the fun is that they're having an amazing duel and a conversation with each other at the same time.

It's definitely and delightfully different. Bar one flip, the actors, Cary Elwes and Mandy Patinkin, both performed all this scene themselves which is even more impressive.

For the safety of kids or for adults who do not wish to spend too much on their outfit, I'd advise a plastic fencing sword. Look for a toy Musketeer sword or a plastic faux fencing foil to use.

Many adults choose to buy real rapier fencing swords in a Renaissance style but be aware that the point on these will be sharp so they are definitely not a toy.

sword frog belt hanger for cosplay costumes

Get a Sword Frog Belt Hanger to Hold Your Sword from Amazon.com

So how do you stylishly hang a sword from your costume so you can carry it around hands-free? Well for that you need one of these and this is the exact version that a lot of people seem to pick for their pirate outfits because it is made in a medieval style from black leather.

The Final Extras for the Twue-ly Serious Fans

The Princess Bride Dread Pirate Roberts Westley Costume Guide for Halloween and Cosplay ROUS rat

Image Credit: Shared by Phil Gold on Flickr with a CC License

How complete you want to make your whole look is entirely up to you. Whether you just want the absolute basics for Halloween or you want to go the extra mile for cosplay or comic con etc.

These are additional pieces that you don't have to use but they really can finish off the whole look properly.

Even Get Your Own R.O.U.S Rodents of Unusual Size Plush

Princess Bride Rodent of Unusual Size Stuffed Toy 100% polyester faux fur Stuffed toy has button eyes and nose Appliqued foam teeth and felt claws Officially licensedPrincess Bride Rodent of Unusual Size Stuffed Toy 100% polyester faux fur Stuffed toy has button eyes and nose Appliqued foam teeth and felt claws Officially licensed

 

1) A Pair of Black Gauntlet Gloves: Westley wears black leather gloves as part of his fearsome pirate attire.

The gloves are in a gauntlet style which means that they cover over his cuffs on his long-sleeved shirt so you cannot see any flesh. It adds to the whole over-the-top black clothing.

Medieval Ring Belt BlackTough Gloves Men's Ultra Enforcer Leather Gauntlets Size 9 Color BlackHugger Glove Company Men's Classic Unlined Seasonal Wind Stopper Gauntlet (Large)4'' Wide 90 Long Simple Ribbon Sash for Formal Wedding Dress Belts (Black)

2) Plain Black Bandana Belt Sash: Around his waist he wears a wide plain black fabric sash with the ties hanging down quite low. It goes over the top of his tight pants (trousers) and shirt and shows off his slim figure. You could always buy some plain fabric to make one yourself.

3) Medieval Ring Belt: When he's not dueling, over the top of the sash is a medieval style ring belt.

This part is needed for the frog belt hanger which the fencing sword is sheathed in. You could wear a modern style belt but it wouldn't have the right styling to it.

Princess Bride Dread Pirate Roberts Costumes

Adult Princess Bride Westley Costume including shirt, pants, Sash, Head Scarf, Eye Mask and a Pair of GlovesTHE PRINCESS BRIDE WESTLEY BOYS COSTUME dread pirate roberts boy child kids outfit

 

HalloweenCostumes.com make their own officially licensed Dread Pirate Roberts costume which includes most of what you need in order to dress as this character.

The set includes a black shirt with the lacing design at the front, black pants with elasticated waist, a waist sash, head scarf, eye mask and a pair of gloves.

The sword and boots are not included but you can add on your own. If you scroll back up this page, I have further details on these accessories and what you need to get. You could also add on a medieval ring belt and a frog belt hanger to carry a sword around.

Dress as the Dread Pirate Roberts Westley from The Princess Bride

Get this Dread Pirate Costume Set from TheModestMaiden on Etsy

It is possible to get some custom made designs for both adults and kids made to measure. I recommend going to Etsy for this because there are some very good stores that cater for the more serious cosplayers.

You can check out reviews easily enough on Etsy and ask questions from the store owner before you buy. I liked the look of this set above which includes:

  • Cotton Shirt w/front lacing
  • Stretch twill pants w/zipper and snap closure
  • Waist sash
  • Genuine leather belt w/snap closure for easy adjusting
  • Genuine leather mask w/Elastic strap
  • Head scarf
  • Faux leather boot covers

Check out all the current Dread Pirate costumes on Etsy!

You Should Look Something Like this When Done!

princess bride dread pirate roberts westley the man in black hero

Image Credit: Cropped Image Shared by Vladeb on Flickr with a CC License

Here is someone on parade and striking a pose for the camera. If you can pull off a look even close to this one, you should be the hottest hero around.

Westley started out as a simple Farm Boy but it was his true love for Buttercup, or should that be "twu wuv," that prompted him to go off and seek a fortune so they could be together.

His journey turned him into a legendary hero and the most feared swashbuckler of them all. Really he isn't actually the said character at all. As he explains later on, the reputation that goes along with the name is the thing that actually inspires the fear. So there's hope for us all then!

NOW Come See My Own DIY Dread Pirate Roberts Cosplay Outfit and How I Put it All Together

The Princess Bride is a real favorite of mine and I love both the movie and also the book too. The book version is awesome if you skip the rather unnecessary intro and footnotes by the author: William Goldman.

I hope you had fun using my extensive guide on this character for Halloween or cosplay. If you want to do some real justice to this masked hero's outfit, practice becoming a skilled swordsman and learn how to use the Bonetti's Defense, Capa Ferro, Thibault and Agrippa.

Oh and you'd better be just as amazing, if not better, with your left hand too! Only tall, suave and very handsome heroes need apply. You'll be inspiring a lot more when you take this awesome character on.

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Articles are accurate and true to the best of the author’s knowledge. Content is for informational or entertainment purposes only and does not substitute for personal counsel or professional advice in business, financial, legal, or technical matters.





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