I can indeed! In fact, I’d be more than happy to!
Dean Winchester. You know him. You love him. You want to be him… Well, only for a day, because then you can take everything off and not have to deal with dead parents, crippling self loathing and the apocalypse and all that. And I’m going to tell you how.
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My credentials? Well, I cosplay as Dean, too. I don’t claim to be the best Dean out there, but I am probably in the running for most anal retentive when it comes to details and screen accuracy. If you’re wondering what I look like as Dean, voila:

I am going to break this costume guide into three major categories:
Clothing
Accessories
Hair and, yes, makeup
Now, are we ready? Seated comfortably? Got your bag of pork rinds and/or sandwich? GREAT!
Clothing:
What Dean’s outfits are comprised of will vary from season to season, however the main idea stays the same. Dean normally wears a minimum of two layers, but typically can be seen in three. His standard outfit is comprised of the following:
Bootcut jeans, generally stone washed denim, with several holes worn through them
A dark solid color crew neck t-shirt, despite fan fiction’s propensity for putting him in band t-shirts. His most common color choices are black and grey, sometimes he wears navy blue.
An overshirt. Despite the jokes about the Winchesters and plaid, it’s actually Sammy who usually wears the most plaid. Dean wears solid colors, though he does have a few plaid shirts. His favourite is a greyish green workshirt, but he also frequently wears navy blue work shirts, and he also has a red one (which is actually the best color on Jensen Ackles, it brings out his eyes). He has three main plaid ones I can think of off the top of my head, a tan one, a dark grey one and the infamous red and white one he wears in All Hell Breaks Loose.A.K.A. The Shirt of Creys.
A coat or jacket. Season’s 1-5 heavily featured Dean’s car coat, a vintage Wilson’s coat in brown leather that is almost impossible to find.
There are dupes available, just search “vintage car coat” on ebay and look for one with similar collars/lapels and button closure. I was able to find a Gap coat that is pretty much a dead ringer, minus the cross seam in the back:
Easier to find by far is one of Dean’s several military style jackets. The one he wears the most often is an olive green one from Gap (it’s called “Military Commander Slub Twill Jacket”). He also has one in grey, and one in navy blue.
The boots that Dean wears vary from season to season. Best that I can tell, he tends to favor vintage lace up motorcycle boots in brown leather. They look a lot like Red Wings.
Variations from this norm:
Henleys. He has a few, normally we see him in either the grey one, or a black waffle texture one. In Everybody Loves A Clown, he even wears one with no overshirt and the car coat. Fuck, they need to do that more often.
Costumes. FBI suit, hospital scrubs, gym coach, 1940’s, cowboy, LARP, etc. He has a few. They’re entirely different entities, so I won’t cover them in detail.
Occasionally he will wear a v-neck t-shirt, but that’s a small detail, so unless you’re doing an outfit where he specifically wears a v-neck, I would stick to crew.
Also occasionally, he will only wear a t-shirt. This is typically when he’s working on a car, digging himself out of a grave, etc. Usually in these instances he wears his overshirt tied around his waist. He looks almost naked when this happens, fer real.
Accessories:
You’re probably noticed that Dean wears a lot of jewelry. True facts, this is because Jensen Ackles likes jewelry (you’ve probably seen how he loves wearing rings and leather bracelets), and thought that Dean being a hunter would have a lot of protective amulets and such all over him. So he picked out some stuff for Dean to wear from a box of random shit wardrobe gave him, and the showrunners said they’d make stories behind them. Only one piece of Dean’s jewelry really does have a story behind it though, and is:
The Samulet. Renowned. Infamous even. Obviously, if you’re wearing this it means you’re cosplaying as an earlier season incarnation of Dean, because he stops wearing the Samulet in early season 5 (creys). However, I’ve noticed it’s one of those details you kind of need to have in order to cosplay as Dean. He a hard character to be recognized as in most situations, and the Samulet is one of those details that people tend to look for. Now, where to get one? Ebay or amazon. A word of advice though, don’t buy this one:It’s flat. And don’t buy the tiny one either. My brother bought me that one, it’s literally like a centimeter tall, it’s minuscule. The best mass produced one I’ve found looks like this:A bit shiny but you barely even notice in photos. Plus, it tarnishes pretty quickly. An advantage of it being cheap, lol. But if your budget allows for it, jump on the opportunity to get one like this:There’s always at least one on ebay, and they typically cost about $100-200. That particular one is about $180.
Dean’s other accessories generally include a silver ring on his right hand (started off as a prop Celtic pewter ring, when Danneel and Jensen got married though he apparently just started wearing his wedding ring on his right hand because he didn’t like not wearing it), a large, black plastic watch, an elephant hair bracelet, and a Tibetian bracelet of skull beads. The real deal is hard to get a hold of for most of these (minus the ring, which you can find at any store for about $10, and the watch which you can get a similar one at Walmart), but they are easy to replicate. There is a tutorial on how to make an elephant hair bracelet floating about (though I suggest making it out of leather cord, lol), and the beaded bracelet can be made out of any beads that look like skulls, painted various shades of brown and strung onto some sort of cord. The watch is worn on the left hand. The bracelets and ring are worn on the right.
Hair and Makeup:
Dean’s hair is pretty standard as far as haircuts go, but damn is it hard to achieve as a cosplayer. In fact, I cut and dyed my hair to match his for seven months just in order to cosplay as him, because I couldn’t find a wig that would work. The problem being the fact that his hair is short enough to expose scalp on the sides:

As I said though, it’s a pretty standard haircut if you’re looking to get it yourself. Ask your hair dresser for a crew cut with some length on top. About 1 1/2-2 inches of length. The sides should be about a #4 (clipper speak for 1/2 inch) graduate down to a #3 (3/8 inch). Show them a picture of Jensen too. And make sure they know to NOT TAKE TOO MUCH OFF THE TOP NO MATTER HOW MUCH THEY WANT TO. Assure them that you need a little bit of length to style. So many times have I gone to get a trim while I had this style and returned home looking like a freshly shaved cadet and had to grow my hair out a bit before the con. Too many times.

Seriously, I had like no hair, it was not the best look for me.

If you’re female bodied and unable to grow your own sideburns, ask them to keep them when you get the haircut, tell them to trim the straight across mid ear.
If you need to dye your hair to match Jensen’s (which is a very light ash brown), take lots of precaution in order to ensure you hair does not go brassy. Use a bleach that adds cool tones, and add some cool violet additive to your dye. Wash with a violet shampoo intended for silver and bleach blonde hair. The dye I used was Wella Color Charm in 336 Light Brown Intense Ash. You have to touch up literally every four weeks though, because believe me, your roots will grow in FAST.
Wig options? Alas, generally “spend a lot of money.” The wig I very desperately am trying to save up for is a full lace wig made of human hair, eliminating the exposed scalp problem (you literally cannot cut a wefted wig short enough to match Dean’s hair length). You can find it here. The closet other “inexpensive” (only not really) option I found was this wig, which is still a bit long, but can be trimmed down and styled to resemble Dean’s Season 1 hair, which was a bit longer. I’m still debating whether 10SP14 or 38 would be the best shade for that wig. 38 technically contains grey fibers, but it reads as light brown, the grey ashing out the overall color.
Makeup is pretty standard, FtM contouring if you need it, a few freckles added with a very light brown eye pencil if you really want to (you want them to look like they’re a part of your skin, not sitting on top of it, making you look like Howdy Doody), and for me, the tiniest bit of green eye enhancing mascara and some lipstain layered with carmex to make my lips look shiny, flushed and large without looking glossed. You can add some blood too, if you’d like. I enjoy doing that.

Now, I have naturally green eyes, but if you really desperately want them and you don’t have them, contacts are your friend. Now, there are many different kinds of green eyes. My girlfriend and I both have green eyes, but they aren’t even remotely the same color. Hers are almost a grey, very cool toned, and mine are more of an olive, with flecks of gold and amber in the center, very warm toned. Jensen Ackles’s eyes are the same way, a warmer green (though green itself is a cool color and this a bit of an oxymoron. Bear with me).
Most green color contacts out there will make your eyes the cooler toned green, almost a jewel tone. Dean’s eyes aren’t like that. Go for a green with some golden tones in it, like Puffy 3 tones.
Well, okay then! I hope I’ve given you guys some insight into how to cosplay as Dean, especially considering this took me about an hour and a half to write. Good luck, and happy cosplaying! If you have any more specific questions, feel free to ask!

I can indeed! In fact, I’d be more than happy to!

Dean Winchester. You know him. You love him. You want to be him… Well, only for a day, because then you can take everything off and not have to deal with dead parents, crippling self loathing and the apocalypse and all that. And I’m going to tell you how.

My credentials? Well, I cosplay as Dean, too. I don’t claim to be the best Dean out there, but I am probably in the running for most anal retentive when it comes to details and screen accuracy. If you’re wondering what I look like as Dean, voila:

I am going to break this costume guide into three major categories:

  • Clothing
  • Accessories
  • Hair and, yes, makeup

Now, are we ready? Seated comfortably? Got your bag of pork rinds and/or sandwich? GREAT!

Clothing:

What Dean’s outfits are comprised of will vary from season to season, however the main idea stays the same. Dean normally wears a minimum of two layers, but typically can be seen in three. His standard outfit is comprised of the following:

  • Bootcut jeans, generally stone washed denim, with several holes worn through them
  • A dark solid color crew neck t-shirt, despite fan fiction’s propensity for putting him in band t-shirts. His most common color choices are black and grey, sometimes he wears navy blue.
  • An overshirt. Despite the jokes about the Winchesters and plaid, it’s actually Sammy who usually wears the most plaid. Dean wears solid colors, though he does have a few plaid shirts. His favourite is a greyish green workshirt, but he also frequently wears navy blue work shirts, and he also has a red one (which is actually the best color on Jensen Ackles, it brings out his eyes). He has three main plaid ones I can think of off the top of my head, a tan one, a dark grey one and the infamous red and white one he wears in All Hell Breaks Loose.


    A.K.A. The Shirt of Creys.
  • A coat or jacket. Season’s 1-5 heavily featured Dean’s car coat, a vintage Wilson’s coat in brown leather that is almost impossible to find.

  • There are dupes available, just search “vintage car coat” on ebay and look for one with similar collars/lapels and button closure. I was able to find a Gap coat that is pretty much a dead ringer, minus the cross seam in the back:

  • Easier to find by far is one of Dean’s several military style jackets. The one he wears the most often is an olive green one from Gap (it’s called “Military Commander Slub Twill Jacket”). He also has one in grey, and one in navy blue.
  • The boots that Dean wears vary from season to season. Best that I can tell, he tends to favor vintage lace up motorcycle boots in brown leather. They look a lot like Red Wings.

Variations from this norm:

  • Henleys. He has a few, normally we see him in either the grey one, or a black waffle texture one. In Everybody Loves A Clown, he even wears one with no overshirt and the car coat. 


    Fuck, they need to do that more often.
  • Costumes. FBI suit, hospital scrubs, gym coach, 1940’s, cowboy, LARP, etc. He has a few. They’re entirely different entities, so I won’t cover them in detail.
  • Occasionally he will wear a v-neck t-shirt, but that’s a small detail, so unless you’re doing an outfit where he specifically wears a v-neck, I would stick to crew.
  • Also occasionally, he will only wear a t-shirt. This is typically when he’s working on a car, digging himself out of a grave, etc. Usually in these instances he wears his overshirt tied around his waist. He looks almost naked when this happens, fer real.

Accessories:

You’re probably noticed that Dean wears a lot of jewelry. True facts, this is because Jensen Ackles likes jewelry (you’ve probably seen how he loves wearing rings and leather bracelets), and thought that Dean being a hunter would have a lot of protective amulets and such all over him. So he picked out some stuff for Dean to wear from a box of random shit wardrobe gave him, and the showrunners said they’d make stories behind them. Only one piece of Dean’s jewelry really does have a story behind it though, and is:

  • The Samulet. Renowned. Infamous even. Obviously, if you’re wearing this it means you’re cosplaying as an earlier season incarnation of Dean, because he stops wearing the Samulet in early season 5 (creys). However, I’ve noticed it’s one of those details you kind of need to have in order to cosplay as Dean. He a hard character to be recognized as in most situations, and the Samulet is one of those details that people tend to look for. Now, where to get one? Ebay or amazon. A word of advice though, don’t buy this one:

    It’s flat. And don’t buy the tiny one either. My brother bought me that one, it’s literally like a centimeter tall, it’s minuscule. The best mass produced one I’ve found looks like this:


    A bit shiny but you barely even notice in photos. Plus, it tarnishes pretty quickly. An advantage of it being cheap, lol. But if your budget allows for it, jump on the opportunity to get one like this:


    There’s always at least one on ebay, and they typically cost about $100-200. That particular one is about $180.
  • Dean’s other accessories generally include a silver ring on his right hand (started off as a prop Celtic pewter ring, when Danneel and Jensen got married though he apparently just started wearing his wedding ring on his right hand because he didn’t like not wearing it), a large, black plastic watch, an elephant hair bracelet, and a Tibetian bracelet of skull beads. The real deal is hard to get a hold of for most of these (minus the ring, which you can find at any store for about $10, and the watch which you can get a similar one at Walmart), but they are easy to replicate. There is a tutorial on how to make an elephant hair bracelet floating about (though I suggest making it out of leather cord, lol), and the beaded bracelet can be made out of any beads that look like skulls, painted various shades of brown and strung onto some sort of cord. The watch is worn on the left hand. The bracelets and ring are worn on the right.

Hair and Makeup:

Dean’s hair is pretty standard as far as haircuts go, but damn is it hard to achieve as a cosplayer. In fact, I cut and dyed my hair to match his for seven months just in order to cosplay as him, because I couldn’t find a wig that would work. The problem being the fact that his hair is short enough to expose scalp on the sides:

As I said though, it’s a pretty standard haircut if you’re looking to get it yourself. Ask your hair dresser for a crew cut with some length on top. About 1 1/2-2 inches of length. The sides should be about a #4 (clipper speak for 1/2 inch) graduate down to a #3 (3/8 inch). Show them a picture of Jensen too. And make sure they know to NOT TAKE TOO MUCH OFF THE TOP NO MATTER HOW MUCH THEY WANT TO. Assure them that you need a little bit of length to style. So many times have I gone to get a trim while I had this style and returned home looking like a freshly shaved cadet and had to grow my hair out a bit before the con. Too many times.

Seriously, I had like no hair, it was not the best look for me.

If you’re female bodied and unable to grow your own sideburns, ask them to keep them when you get the haircut, tell them to trim the straight across mid ear.

If you need to dye your hair to match Jensen’s (which is a very light ash brown), take lots of precaution in order to ensure you hair does not go brassy. Use a bleach that adds cool tones, and add some cool violet additive to your dye. Wash with a violet shampoo intended for silver and bleach blonde hair. The dye I used was Wella Color Charm in 336 Light Brown Intense Ash. You have to touch up literally every four weeks though, because believe me, your roots will grow in FAST.

Wig options? Alas, generally “spend a lot of money.” The wig I very desperately am trying to save up for is a full lace wig made of human hair, eliminating the exposed scalp problem (you literally cannot cut a wefted wig short enough to match Dean’s hair length). You can find it here. The closet other “inexpensive” (only not really) option I found was this wig, which is still a bit long, but can be trimmed down and styled to resemble Dean’s Season 1 hair, which was a bit longer. I’m still debating whether 10SP14 or 38 would be the best shade for that wig. 38 technically contains grey fibers, but it reads as light brown, the grey ashing out the overall color.

Makeup is pretty standard, FtM contouring if you need it, a few freckles added with a very light brown eye pencil if you really want to (you want them to look like they’re a part of your skin, not sitting on top of it, making you look like Howdy Doody), and for me, the tiniest bit of green eye enhancing mascara and some lipstain layered with carmex to make my lips look shiny, flushed and large without looking glossed. You can add some blood too, if you’d like. I enjoy doing that.

Now, I have naturally green eyes, but if you really desperately want them and you don’t have them, contacts are your friend. Now, there are many different kinds of green eyes. My girlfriend and I both have green eyes, but they aren’t even remotely the same color. Hers are almost a grey, very cool toned, and mine are more of an olive, with flecks of gold and amber in the center, very warm toned. Jensen Ackles’s eyes are the same way, a warmer green (though green itself is a cool color and this a bit of an oxymoron. Bear with me).

Most green color contacts out there will make your eyes the cooler toned green, almost a jewel tone. Dean’s eyes aren’t like that. Go for a green with some golden tones in it, like Puffy 3 tones.

Well, okay then! I hope I’ve given you guys some insight into how to cosplay as Dean, especially considering this took me about an hour and a half to write. Good luck, and happy cosplaying! If you have any more specific questions, feel free to ask!