Supernatural Chat: Sam and Dean Play Dress-Up – What’s Your Favorite Winchester Costume?

Supernatural - Sam and Dean costume collage

Hey there Supernatural fans. How are y’all surviving the hellatus? Still hanging in there? Well, just remember that as of now we have less than one month to go. We’re in the home stretch people! We can do this!

To get us through the next few weeks, I decided to go for a fun post chock full of what I hope everyone will agree is some pretty nice Winchester eye candy. You gotta love the fact that Supernatural is the type of show that gives our favorite guys a chance to change it up every once in a while and dress in different costumes. While some are hilarious and others are sexy, all are sure to bring a smile to a fangirl or fanboy’s face.

I’ve picked out a few examples of Sam and Dean playing dress-up, check them out below.


Though we can’t see the boys’ faces or even much of their bodies in this bulky gear, who doesn’t enjoy seeing the Winchesters dressed up as firefighters? I’m sure a lot of people (like Dean) wanted to be firefighters when they were little and even if you never wanted to be one, chances were you wanted to be rescued by one (especially if said firefighter turned out to be a Winchester).


Okay so no, I most certainly have not ever had fantasies about Sam and Dean dressed as priests. No really, I mean it. Okay so yeah, maybe the Chippendale version from the blooper reel where they cut off the sleeves but c’mon I’m only human.


Folsom Prison Blues was the first episode of Supernatural I ever saw (wow, seems like I’ve said that in a lot of my articles recently) so of course I had to include the boys in their prison attire. Is it just me or do Sam and Dean somehow make even an orange jumpsuit look good? Just sayin’.


Once again, the Winchesters manage to take what should be a boring costume and a somewhat boring job (sorry to any repairmen or women out there) and make it look a heck of a lot better. Maybe it’s knowing that when they put on a costume, it means that soon they will be hunting some sort of version of evil, but even in jumpsuits, they look pretty darn good.



Here’s one example where the costumes they chose were already pretty sexy. I mean c’mon now, who *hasn’t* had a cowboy/cowgirl fantasy? Put the Winchesters in the outfits, give them the hats and the guns and boy howdy do they look mighty fine.


SUPERNATURAL - "Red Sky at Morning"

Yet another example of a costume that didn’t necessarily need help from the Winchesters to be sexy. I remember when I first saw the promo pics for Red Sky at Morning and saw the boys in their tuxes, I just about passed out. I think part of the fun of these outfits is the fact that the boys usually never dress up in anything nearly so fancy. I love their normal turnout of boots, jeans and flannel, but it sure was nice to see them in tuxes for a little while.


Supernatural - Sam and Dean as Doctors

Lack of medical knowledge aside (well, unless you count field dressings and stitches done with tooth floss), who wouldn’t perk up at the sight of Sam or Dean walking in to your hospital room? With those white coats and scrubs, the boys almost don’t look like the Winchesters and yet somehow they look even better.

FBI Agents (or anyone in a suit)

Supernatural - Sam and Dean as FBI Agents

The first couple episodes of Supernatural showed the Winchesters wearing only jeans and flannel shirts so when they dressed up in suits for the first time, I definitely sat up and took notice. I remember early on that my friends and I got so excited whenever we saw them in suits in promo pictures. After that, it began to happen so often that it wasn’t nearly as exciting, but still pretty cool any time they suited up.

Special Mention: Dean’s Wacky (and Cool) Costumes

Supernatural - Dean costume collage

As much as the Winchesters dress up as a matching set, it seems like Dean has gotten more than his fair share of extra costumes as well. Some of them have been downright hilarious and others have been completely sexy, but all of them have one thing in common – Dean.

It seems like no matter what Dean wears, he magically pulls it off. I thought I’d never be able to take him seriously after he wore outfits like the lederhosen and the tiny gym shorts, but somehow even after he takes a dip into the ridiculous, he has no trouble coming back to be the badass Dean we all know and love.


Those are just a few of my favorite costumes from Supernatural over the years. What about you folks? Got any favorite Winchester costumes? Sound off in the comments below. I love hearing from you guys!

”Supernatural Chat” is published every Tuesday. If you’re curious what this column is all about, check out our introductory post on it and more articles here.

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