
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.
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:
Close Match: Replica Supernatural Jacket
Exact Match: Dickies Work Shirt
Close Match: Lucky Brand Jeans
Close Match: Men's Logger Boots
Close Match: Replica Dean Winchester Ring
Close Match: Replica Dean Winchester Necklace
Exact Match: Suunto Core Wrist Watch
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

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?

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, Amazon.com 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

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.
Conclusion
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.