How To Get Into Dean’s Pants (Cosplay Part II)

So a couple of weeks ago I wrote an article on cosplaying Dean, covering his jackets and shirts.  This week I’m going to finish it up by getting into his pants…and his footwear and other accessories.

Dean Winchester Destroyed JeansGet Into Dean’s Jeans

Believe it or not, the style of jeans that Dean wears does slightly change in Supernatural.  Early on in the show (the first few seasons at least) he tended to wear jeans that were more destroyed and torn up looking.  We’re talking huge holes here, like the size of an adult’s fist.  Dean always has the “bad boy” look, but he really kicked it off in the first few seasons with his awesome leather jacket and torn up jeans.

Not only does he tend to wear more worn out jeans at first, his jeans also fit a bit more loosely.  I’m not saying that Dean ever wears tight jeans, but they’re definitely a looser fitting style.  And coming back to the more torn up look, the bottom of his jeans (literally the very bottom) are pretty torn up in a lot of episodes (as if he stepped on them as he walked).

Even in the later seasons though, he never wears what I would call “nice” jeans.  Dean’s jeans are always at least slightly faded, but in the later seasons they usually have less (if any) holes, and the bottoms don’t look like they’ve been continuously stepped on.

What style jeans does he wear though?  I’ve read conflicting information across the internet… Some people claim he only wears straight leg jeans, others say only boot cut.  I’m pretty sure he wears both styles.

Again it seems like this is something that changes as the seasons progress.  He definitely wears boot cut style jeans in the first few seasons, but as times goes on Dean seems to transition to straight leg.  As for the color, stick with blue jeans.  He never wears black jeans (from what I can remember), but the colors run from light, stonewashed to a darker blue.

So what do we have as a recap for Dean’s style of jeans?

  • Destroyed (personal preference on the level of destruction)
  • Good fit (not too loose and not too tight)
  • Boot cut or straight leg
  • Blue jeans (light stonewashed to dark blue…just not black)

If you want to see what jeans I picked out, you can check out either my How to Dress Like Dean page or the Dean Winchester Costume page.  The costume page is basically just pictures of the clothing/accessories with links to buy them on, the other page is an actual article (but still includes links on where to buy everything).

Big Boot Style

Dean’s boots…they go well with his leather jacket :)  Through almost the entire series he sticks to logger style boots.  Logger boots have large heels and are usually at least 8″ tall (from top to bottom).  In some promo shots for season one, I think he does wear Caterpillar Akon boots, but I don’t recall ever actually seeing them in an episode of Supernatural.

My personal favorite boots of Dean’s are the brown/reddish logger style boots that he seems to wear the most often. Everything I’ve read that claims to know what type of boots they are say they’re Rocky GorTex insulated logger boots.  They look exactly the same from what I can tell, but I’ve never seen a screen cap that proves they’re the same boots.  It doesn’t really matter, of course.  You just need something that’s almost identical, even if it may not be exact.

Dean Winchester's Shoes Season 1 Episode 3Dean does go without wearing boots in Supernatural, but it doesn’t happen very often.  For example, in season one, episode three, dean has these distinct shoes (not boots) shown in the picture.  I’m sure there are times other than just that episode when Dean doesn’t wear boots for his footwear, but that episode/those shoes have always stuck in my mind for some reason.

What are you looking for in the footwear part of your Dean Winchester cosplay?

  • Boots (duh!)
  • Logger style (tall, large heels)
  • Brown/slightly reddish in color

Again, if you want to read a few other things I’ve written on Dean’s boots, its on the How to Dress Like Dean page.

The Little Stuff (Belt, Ring, Watches, etc.)

I did find a few screen captures of different belts Dean wears, but they’re all really similar and usually pretty generic.  They’re typically wide, black or brown colored leather belts.  That’s why on my Dean costume page and accessory page I just link to a brown leather Carhartt belt.  When it comes to Dean’s belts, you want to keep it simple and manly.  Nothing fancy going on here (and there shouldn’t be).

Replicas of Dean’s silver ring can be found all over the internet, so that’s definitely not something that’s going to be difficult to find for your cosplay.  That is, assuming you’re going for the version of Dean in seasons one through five.  After season five, episode seven, Dean stopped wearing his silver ring.

It’s a good thing fans of Supernatural are so curious about the show, because a few of the exact watches Dean wears on the show have been identified.  Throughout season one, Dean wears this Smith & Wesson S.W.A.T. black rubber strap watch.  It definitely matches the rough and rugged style the Winchesters obviously prefer.  Later on in the show, Dean can be seen wearing the MTM Black Patriot, and also the Suunto Core.  These last two watches are kind of expensive though.  The Suunto usually runs $300+ and the MTM $500+.  I guess Dean has been running a lot of credit card scams…and maybe a bit of pool on the side to afford those watches.

Dean Winchester Cosplay Suunto Core

Although the prices are kind of all over the place on those watches, they all have one thing in common: their style.  Sure, some of them might do it in a fancier (maybe better?) way, but in the end they’re all  military/rugged/outdoorsy types of watches.

Oh, and let’s not forget Dean’s necklace.  It holds a lot of significance in the show (in my mind).  You find out pretty early on in the show (season three, episode eight) that Sam gave it to Dean as a Christmas present when they were younger.  Later on (in season five) Castiel reveals that it could be used to find God.  Dean ends up throwing it away in episode 16 of season five when they find out God is masking himself from the amulet.  So once again, another accessory that Dean wears and is never seen again.  Like with the ring, you can find replicas on Amazon if you’re interested in buying one.

Last but not least (well, maybe least), a couple of different bracelets Dean wears.  I didn’t know it before I started looking into my Dean Halloween costume, but one of the bracelets Dean wears is supposed to be made out of elephant hair.  I figured it meant that elephant hair had some sort of significance, so I looked it up.  Elephant hair bracelets are supposed to bring the wearer good luck.  I don’t think you’d be able to find an actual elephant hair bracelet, but Amazon does sell some replicas.

The other bracelet I found that he wears is a skull bracelet.  I don’t think this one has any significance (someone correct me if I’m wrong) though, and from what I could find, he doesn’t wear either bracelet past season two. Amazon sells a replica of this bracelet too.

What do we take from this?

  • Wear a rough/military/outdoorsy style watch

And that’s really it.  All of Dean’s other accessories are pretty inconsistent throughout Supernatural, so you can choose whichever ones you like best, or none at all, and you’ll still be staying true to your Dean cosplay.


I guess getting into Dean’s pants isn’t so difficult after all.

I feel like we covered a lot of stuff here, but I wanted to try to be pretty comprehensive.  I know I’ve found the shoes that Dean wears for sale online in the past, but I can’t seem to find them now.  If I do ever find them, I’ll make sure to update the article.  Or if any of you know where to buy them, please let me know in the comments down below.


  1. Dano93 July 12, 2014 at 10:50 am

    • Allen Jones July 12, 2014 at 3:03 pm

  2. I believe there is a god, but i am not sure he still believes in us. August 6, 2017 at 8:30 am

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