How to Dress Like Dean Winchester

How to Dress Like Dean Winchester

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.  If you’re just interested in the clothes/accessories and where to buy them, check out my costume page.

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?

Dean Winchester Clothes vs Real Products

Item Name & ImageScreen Cap of Clothing/Accessory
Replica of Dean
Winchester's Original
Leather Jacket
Replica Dean Winchester Leather Jacket
Dean Winchester's leather jacket and shirt
Wilson's Replica Dean Winchester Leather Jacket
Wilsons Replica Dean Winchester Jacket

Dean Winchesters leather jacket and shirt
Dickies Long Sleeve
Work Shirt (multiple colors)
Dean Winchester Costume Dickie's Work Shirt
Dean Winchester Dickies shirt
Carhartt Long Sleeve
Work Shirt
Dean Winchester Carhartt Long Sleeve Button Up Shirt
Dean Winchester Red Carhartt Long Sleeve Shirt
Lucky Brand Jeans
Lucky Brand Bootcut Jeans
Dean Winchester rocking out
Chippewa Logger Boots
Chippewa Logger Boots
Dean Winchester's Boots
Rocky GorTex Logger Boots
Dean Winchester Rocky GorTex Logger Boots
Dean Winchester's Boots

Dean Winchester leather jacketDean 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.

Where to Buy Dean’s Leather Jacket

I ended up ordering this replica Supernatural Dean Winchester leather jacket through (multiple sizes are available).

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 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.

For details on more of Dean’s jackets, check out my page on Dean Winchester’s jackets.

Dean Winchester Dickies work shirtWhat 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.  If you want information on some of Dean’s other shirts, you can check that out here.

Where to Purchase Dean Winchester’s Work Shirts

Once again, comes to the rescue.  You can find the Dickies work shirts here, Dickies Men’s Slim Fit Long Sleeve Work Shirt.  And here is the Carhartt shirt, Carhartt Men’s Oakman Work Shirt, Dark Red.

Just to be clear, all colors and sizes are available.

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 Men’s Premium Denim 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).

Dean Winchester's Boots

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: Carhartt Men’s 3691 8″ Logger Boot.

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

I’ve also read claims that Dean has worn Rocky GorTex logger boots.  You can find the Rocky’s here, Rocky Men’s 9″ Great Oak Waterproof GorTex Insulated Logger Boot.


If you’re looking for details about Dean’s different watches, bracelets, etc., I cover all of that on my accessories page.

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.

Would you rather dress pretty much the same or add your own style?


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