How to Dress Like Dean Winchester (Supernatural) | TV Style Guide

How to Dress Like Dean Winchester

By Matt
Last updated: January 25, 2024
Supernatural Dean Winchester Wilson's leather car coat

After dressing up as Dean Winchester for Halloween, and having such a difficult time in finding out where to find and purchase clothing/accessories similar to what he wears on Supernatural, I decided to write my own little guide on dressing like him.

Please consider supporting us on Patreon 🙂

Finding “Dean Winchester clothes” isn’t as easy as you’d think. But I’ve already gone through the trouble, I might as well make it easy on the next person, right?

If you're looking for more detail and variety on Dean's shirts, check out my article here.  For my article on his jackets, that can be found here.  And if you're looking more for his different accessories, you can see that here.

Clothing Purchasing Guide

We recommend:

Jacket & Shirts

Jeans & Boots

Dean's style overview:

  • Leather car coat
  • Faded straight/bootcut jeans
  • Solid colored t-shirts
  • Logger style boots

Dean Winchester's Leather Jacket

Supernatural Dean Winchester Wilson's leather car coat

We all know and love the leather jacket that Dean gets from his dad, John Winchester. This was one of the hardest things for me to find when I was putting together my costume.

I eventually found a great replica and ordered it. My original intentions were to return the jacket after Halloween, but I actually liked it a lot and decided to keep it.

I ended up ordering this replica Supernatural Dean Winchester leather jacket through Amazon.

I was actually able to purchase all of the stuff for my costume through them. Amazon also has a great return policy, so if you decide you don’t want to keep anything you can always return it. Usually if you have to pay anything, it’s just the return shipping. Of course you could end up like me and just keep the jacket because it’s so awesome.

His original leather jacket was a Wilson’s M. Julian car coat, but it was only made in the 90’s. That Wilson’s jacket isn’t made anymore, but Wilson’s does sell a replica of Dean’s jacket now.

It wasn’t available when I bought my replica off of Amazon, but here is a Wilson’s leather jacket replica. I don’t own this jacket, but since they made his original one, I’m sure there are people who would rather get it from Wilson’s.

What Shirts Does Dean Wear?

Supernatural Dean Winchester gray tshirt

Most of the long sleeve button up shirts he wears are Dickies work shirts. As far as colors go, Dean usually sticks with khaki/brown, black, grey and dark/earth greens. Actually, when I think, “Dean Winchester clothes”, those are always the colors that come to mind.

He does occasionally wear a red button up work shirt, but that’s a Carhartt brand. Not that it makes much of a difference, as both Dickies and Carhartt are excellent brands.

Where to Purchase Dean Winchester's Work Shirts

Once again, comes to the rescue. You can find the Dickies work shirts here. And here is a good alternative for the Carhartt shirt.

Dean's Jeans

This was actually one of the easier parts of Dean’s clothing to match. The older Winchester generally wears distressed jeans that are a slimmer fit. He doesn’t wear “skinny jeans”, but they aren’t baggy either. Dean Winchester clothes are always the perfect fit.

Where to Buy Dean Winchester's Jeans

You can probably go to most major clothing retailers and find a pair of jeans similar to the ones Dean Winchester wears, but these distressed jeans are a pretty good match.

Dean's Boots

Supernatural Dean Winchester logger boots

What kind of boots does Dean Winchester wear? He wears a wide variety of boots on Supernatural, but the most common ones are a logger style boot.

As far as I could tell through my research, you can never tell exactly what brand of boots he’s wearing. Not to worry! There are at least a couple different styles/brands that look really similar (if not the same).

Where to Purchase Dean Winchester's Boots

Again, I bought mine through Amazon. I think these boots look almost identical to Dean’s, especially when wearing the right jeans: Chippewa logger boots.

The boots I bought were actually made by Frye’s, unfortunately they’re not sold anymore. The Chippewas I linked above look almost identical to the boots I bought. And more importantly, almost identical to the boots Dean wears.


In my opinion, the way Dean dresses is awesome. It looks great, works for almost any situation, and you keep a pretty manly look.

Since dressing up as him for Halloween a few years ago, I’ve actually adopted the style myself. I don’t wear the exact same clothes he does, I’ve given it my own touch.

About the author


I'm a huge fan of sci-fi/supernatural/monster type shows. After putting together some of my own custom costumes and outfits from TV characters, I decided to start writing my own guides.

Tiffany - July 8, 2014

I have a question… Where can you get the military style jackets? I’ve looked everywhere.

    Matt - July 8, 2014

    Hi Tiffany, have you checked my page on Dean’s different jackets? Here is the URL:
    If it’s not covered on that page, let me know which jacket you’re talking about exactly and I’ll do what I can to find out 🙂

      Dean's Girl - April 16, 2016

      I have a pair of Red Wing boots that are similar to Dean’s that I wear. And I love them.

      These are what mine look like:

      They’re not the color of Dean’s but they work just the same.

    Sam - August 27, 2015 this is websit hope u find one but u know hunters dont wear military jackets really 🙂

      Matt - August 30, 2015

      Yeah, the Alpha Industries M-65 is a jacket I talk about on that page.

        Aiden - November 5, 2015

        what are the under shits he wears

    Sam - November 21, 2015

    You can look on amazon

Tyler - October 13, 2014

Hey what about his undershirts? Those are the ones I’ve had some trouble with I thought you’d have an idea!

Eric - November 3, 2014

The military-style jacket Dean wears is very easy to find, actually. They’re basically standard U.S. military M85 field jackets. You can find olive drab ones fairly cheap through military surplus stores/websites. There are manufacturers that also make it in other colors, such as black and camouflage. I hope this helps you out.

    Matt - November 3, 2014

    Hi Eric, and thanks for the tip. A lot of Dean’s jackets (or at least ones similar to his style) can be found at military surplus stores. But the Alpha Industries M65 is the same exact jacket Dean wears, and if I can find the same exact clothes he wears, that’s what I like to share.

    But there are always alternatives, which is good because a lot of the clothing the Winchester’s wear on Supernatural isn’t cheap.

Eric - November 3, 2014

For the undershirts just look to traditional “worker” brands such as Carhartt, Dickies, etc. I picked up a few from Bass Pro Shop that are Magellan Outdoor brand and they are extremelly good quality for a low price. With Carhartt you’ll be shelling out a good bit of cash per button down so Magellan is a great brand if you’re wanting the look but are on a budget. That said, however, I do find Carhartt to be the Cadillac of work clothing overall. He also wears plaid on occasion, most likely flannel, though that’s more Sam’s thing. Black and gray t-shirts tend to be his standard base layer.

    Matt - November 3, 2014

    Hey Eric, thanks again for the tips on Dean’s clothing. I like the comparison of Carhartt to the “Cadillac” of work shirts 🙂 It’s true though, their clothing is very durable and lasts a while.

      Eric - September 1, 2015

      Allen, true story. I’ve owned the Carhartt Sandstone Sierra jacket in black for over 10 years now. It’s my signature jacket and the thing is a tank. The same as my pair of original Oakley SI Assault Boots. Bought them in 2006 and still wear them to work (nearly) every day even now.

01adrian - November 12, 2014

Do you know of any jacket that dean wears that is for sale who is a bit cheap?

    Matt - November 12, 2014

    I can’t think of any of Dean’s jackets that are less than $100 brand new, but a lot of the jackets Dean wears you can’t even get new anymore anyway. So you can check places like Ebay, or local thrift stores and/or military surplus stores. I cover some of this info on my Dean’s Jackets page, but there are a couple of Gap jackets that aren’t made anymore that can be found on Ebay (I’ve bought a couple). And you can probably find a black M65 field jacket at a military surplus store or a thrift store.

Xeneize1 - November 28, 2014

Wrangler sells many Dean type shirts at good prices (although I prefer Carhartt). My wife buys alot of them for me because she’s a big Dean fan and says I look good in the style 🙂 Also, IIRC, Dean has actually worn a wrangler shirt from their Riggs Workwear line.

    Matt - December 2, 2014

    Yup, Wrangler’s clothing would definitely fit in with Dean’s style. And I think you’re right, I do remember reading somewhere that Dean wore a button up Wrangler shirt 🙂

hovac - November 30, 2014

This site is awesome
I really wondering about dean’s shirt and jaket
Thank u!
Could find about dean’s other leather jaket?
i don’t know exactly but on season9 or 8 dean wearing red leather jaket

    Matt - December 2, 2014

    Hi Hovac, thanks for the kind words 🙂

    I’m pretty sure I know which jacket you’re talking about, there was a short comment discussion about it on my “Dean’s Different Jackets” page. Here’s a link to the comment conversation:

      Jimmy - April 19, 2016

      I wud like to buy the hamster suit dean wore on the episode. We’re can I find it

Bill bob - January 24, 2015

At wallmart has some for 30

August - February 8, 2015

Hey, thanks for making this website, it really helped me with my cosplay! One thing though, I noticed in ‘About A Boy’, Dean has new shoes, and I was wondering if this is the first time we see them or if he had them any earlier, or at the start of season 10? And also, if you know of any good places to find them?


August - February 9, 2015

No not those, and I realize now they’re probably his FBI shoes, but I meant the ones Sam found under the dumpster when Dean went missing. They look something like this:

August - February 9, 2015

Also, I’m a but obsessive and kind of a perfectionist lol so I tried to get as close as I could to Dean’s wardrobe. I looked really closely into the shoes, and from that picture I think they may have altered them this season. I’m not 100% sure, but the boots I got for my cosplay were these:

From the research I did on the early looks at Dean’s boots, I think they’re the closest. (Although, I know his are custom). Just thought I’d throw it out there! :p

    Matt - February 9, 2015

    Oh yeah, and you’re right, those are most likely his FBI shoes.

    And those Chippewa boots you linked do look really really close, very nice find 🙂 I’ll probably add those to the table, especially since the Carhartts I recommend have been out of stock for so long.

August - February 10, 2015

Okay cool!
There may be other Chippewa boots that are better(they have a pretty expansive stock), but yeah I personally love mine 🙂
Super awesome website, man! Definitely a permanent bookmark lol

Deborah Winchester - March 10, 2015

Thank you so much, this website is very helpful!
I’m a huge fan of Supernatural and I love the Winchester-style 😉
I was wearing clothes like them before I watched the show, but now it’s even better to dress like the brothers 🙂

    Matt - March 13, 2015

    Hi Deborah, thanks for the kinds words 🙂

Nexus - March 18, 2015

It makes me glad I live out in the country close to a salvation army store, a store that has a bunch of different work and military clothing (can’t remember the name), and walmart .__. aside from the bracelets and such I can dig up most of this lol. Thanks for the awesome guide, now I have to just figure out that hair.

    Matt - March 25, 2015

    Hey Nexus, glad to be of help! 🙂 You can pretty much make a “Winchester wardrobe” just by going to Sears/Walmart type stores, it’s pretty nice.

John - March 19, 2015

I was wondering, where can I find Dean’s new boots, the ones he’s wearing in Season 10?
These ones:

    Matt - March 25, 2015

    John, I’m not really sure how to answer your question. No one knew the exact boots Dean wore before, and these “new” boots are basically identical to his old ones. The closest thing I can find is what’s already on this website.

      John - March 31, 2015

      Dean’s old boots were Rocky Gore-Tex Logger Boots, an older model, older than the ones currently out by Rocky…The new ones do have some differences, the heel is not as a high, the rings around the lace-holes are different, and the line on the side of the boot doesn’t arch all the way to the bottom of the boot, it just connects to the other line..

        Matt - April 4, 2015

        Gotcha. Whenever I was trying to find all of Dean’s clothes, I wasn’t ever able to find any definitive proof of what brand/model his boots were. The closest I ever saw was a good screencap of the sole of his boots, but that only proved the brand of the sole maker, which apparently is used across a bunch of different boot makers.

          John - April 10, 2015

          I think you’d have to contact the wardrobe person to find out..I currently have the Chippewa loggers, but I’m a perfectionist, and that model is really bulky. So i’m not satisfied.

        Winchester1409 - June 22, 2015

        Hi John,
        Did you find what model it is?

        Aaron Coley - May 6, 2016

        I can’t to seem to find the boots Dean wears. I ordered the same Chipewa boots John did and he’s right, they’re way too bulky. I’m thinking it’s because of the steel toe but I’m not sure. Do you know where I can buy some less bulky boots that look like Dean’s?

          Matt - June 7, 2016

          Yeah, it’s unfortunate. I really like the Frye boots I got years ago, but they aren’t available anymore 🙁 I’m going to look for some more boots, hopefully I can find some close matches.

Click here to add a comment

Leave a comment: