
Although I personally have never dressed up as Sam Winchester, I came across quite a few different articles on his clothing style. Whether you’re interested in their style for cosplay, a Halloween costume, or just because Sam and Dean dress awesome, read on.
Clothing Purchasing Guide
We recommend:
Exact Match: Carhartt Jacket
Close Match: Snap Shirt (White Blue Check 016)
Close Match: Men's Relaxed Straight Jeans
Exact Match: Men's Duke Leather Boot
Jackets
Shirts, Jeans & Boots
Sam's style overview:
- Snap up plaid shirts
- Weathered straight leg jeans
- Blundstone boots
Sam's Jackets

Although Dean is known for wearing quite a few different jackets, his most famous has to be his leather jacket. Sam on the other hand doesn’t seem to have any one jacket he is known for. But with all the research I did, I found quite a few that are either exactly the same, or very similar.
If any of Sam’s outerwear is recognizable, I would say the hooded Carhartt jacket he wears is up there. He starts wearing it really early on, and doesn’t stop until at least season six. I can see why, Carhartt products are well made and made to last (from my own personal experience).
Sam’s style of outerwear changes throughout the show, but some other recognizable ones would definitely be the brown jackets, one suede, one corduroy. He starts wearing these jackets when he begins wearing those long sleeve plaid snap-up shirts.
Where to Buy the Jackets
This Carhartt J130 jacket in carhartt brown looks just like the one he wears on the show. Sam also owns another jacket that seems pretty popular on the show. It doesn’t look quite as warm, and it lacks a hood. This Carhartt Men’s Extremes Arctic-Quilt coat is a pretty good match.
If you haven’t caught on yet, the brothers tend to wear a lot of Carhartt clothing.
Sam also wears a few different hoodies, but not for very long. After season two you’ll rarely see either of the brothers wearing one. But if that’s the look you want to go for, this Hanes hoodie looks pretty close to Sam’s charcoal hoodie.
As for the brown suede and corduroy jackets, I don’t think anyone knows what brand and style they are. Most likely, just like Dean’s jackets, they aren’t made anymore and you’d have to scour E-bay.
But, after searching through Amazon.com, I’ve found a couple very similar looking jackets. This Legendary Whitetails jacket is a really good match to the brown jacket Sam wears.
Supernatural Jeans

The brothers wear similar, if not the exact same types of jeans on the show. So any jeans you find on my dressing like Dean page would work here. But I’ll show you a few examples.
These Buffalo David Bitton straight leg jeans are probably some of the best jeans to look like a Winchester, but really anything that looks similar to those will do.
Their style in Supernatural for jeans is basically slightly destroyed, slim fitting (but not too tight!), and usually with Dean he wears bootcut style (though in the past few seasons he seems to have switched to straight leg).
Snap Style Shirts
Where Dean usually wears some type of Dickies or Carhartt button up work shirt in a solid color, Sam tends to wear a bit nicer looking snap up shirts in plaid.
Obviously Sam wears a lot of different colored plaid shirts, so choose whichever color you like. Or if you’re going for a look specific to an episode, this snap up long sleeve looks a lot like one Sam would wear.
Footwear

Just like Sam’s jackets, his shoes/boots change quite often throughout the show. He wears Chuck Taylor type tennis shoes, a generic looking pair of black shoes, and a pair of slip on boots.
Where to Purchase Sam Winchester's Boots
I think the boots that most look like Sam’s would have to be these Blundstone 550 slip on boots. They look exactly like his boots to me, and they’re the boots I envision when I think of “Sam’s shoes”.
And since we know that Castiel’s boots are Blundstones, it makes even more sense that Sam’s boots would be Blundstones too.