Unbelievably Easy Ways to Cosplay Dean Winchester (Jackets & Shirts)

How do you cosplay Dean Winchester from Supernatural?  I’m going to break down his style into a few sections.  In this post we’ll cover what style of jackets, shirts and T-shirts Dean wears.

Dean Winchester's leather jacket and shirtCosplay: Dean’s Jackets and Their Styles

Of course Dean wears quite a few different jackets on Supernatural.  The most famous being his leather jacket given to him by his dad (John Winchester).  From what I could find, the actual leather jacket used on the show was a Wilson Leather M. Julian, slightly customized.  They don’t make the jacket anymore, but there are plenty of people/companies that make replicas.

It’s safe to say that the majority of Dean’s other jackets have a military style.  He does wear a couple of different jackets that aren’t, but they’re usually plain, solid-colored jackets, a zipper in the front and collared.  What makes them “military style”?  Well they usually have epaulets on the shoulders and large, square pockets on the front of the jacket.

Dean’s Leather Jacket

The style of Dean’s leather jacket is considered a driving coat.  This style of jacket is a bit longer.  Instead of stopping at or just below the waste like most jackets, it stops just above mid-thigh.  With the large front buttons and collar, it’s definitely a unique piece.  I personally own a replica of this jacket, and people compliment me on it all the time.  Even friends who know about and watch Supernatural don’t realize it’s from the show until I tell them.

The fit of this jacket is actually really nice.  You can wear a couple of layers underneath it, or you can wear it with just a T-shirt underneath(just like Dean does).  Since it’s real leather, the more you wear it, the more comfortable it gets.  You could even sand it and put it in the dryer for an even more worn-in look.

Dean’s Military JacketsDean Winchester's Alpha Industries M-65 field jacket

Dean’s military styled jackets come in different colors and fits, but one thing remains the same: when you see them, you think “military”.  From his Alpha Industries M-65 field jacket to his plethora of Gap brand jackets, you’ll find plenty of similarities.

Most of his jackets have epaulets (the things on the shoulders), and some of Dean’s jackets that don’t have them, originally did.  I guess the costume designers on Supernatural like to customize the jackets sometimes.  In most episodes when Dean is wearing the M-65 field jacket, the epaulets are removed.  But there are a few episodes where they’re still attached.

Just remember, rough/rugged and military are what you should think if you’re looking for a style similar to Dean’s.  If you’re curious about where to buy these jackets, or just want to see what I’ve found, check out my page on it here.

Dean’s Shirts

Dean Winchester’s shirt style is simple, and easy to replicate.  Colors generally stay the same throughout the different styles, and you’ll see him with long sleeves, short sleeves, and button ups.

Long Sleeve Shirts

The style here varies from henleys, thermals and button ups.  The button up work shirts are all either Dickies or Carhartt brand.  The only other button up style shirt he wears is plaid, which Carhartt carries a wide variety of.  Dean almost always wears these shirts unbuttoned with a solid colored T-shirt underneath.  These long sleeve button up work shirts are great for wearing over a T-shirt, or layering under one of your Dean Winchester style jackets.

If you’re wearing one of the button up shirts, remember: roll up those sleeves!  Unless he’s got a jacket on over the shirt, Dean always rolls his work shirt sleeves up to just below the elbow.  If you’re wearing a thermal or henley long sleeve shirt to cosplay Dean, go with whatever you’re comfortable with.  Dean wears these shirts both ways.

Short Sleeve Shirts

The look and style of Dean’s short sleeve shirts are pretty much undershirts.  Sure, he wears just a T-shirt and jeans in a few episodes, but it doesn’t happen very often.  Rarely is he seen wearing a T-shirt with any sort of logo or graphic on it, but it does happen.  Grab some black, grey, white and green T-shirts.  Just make sure they fit you well, you don’t want to look like you’re wearing a football jersey.


In my opinion, Dean’s style of dress in Supernatural is pretty timeless.  Heck, he even went back in time in one episode, and his clothing didn’t even seem too out of place.  If you’re cos-playing as Dean Winchester or just love the look, I can see why.  It’s pretty simple and masculine.  I mean, you’re wearing boots, jeans and flannel.  How do you get more manly than that?

If you want to see where to buy the clothing and/or see what I’ve picked out, check out my page on How to Dress Like Dean Winchester.  What do you think about Dean’s style?  Question or comment on this article?  Let me know below.


  1. Rachel June 21, 2014 at 3:14 am

    • Allen June 21, 2014 at 5:26 am

  2. Jessica September 2, 2016 at 10:20 am

  3. 86Del August 21, 2017 at 12:55 pm

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