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Making it Work: Dressing the Winchester Way

Well, dahlings, we are here to discuss the fabulous and sometimes fabulously hideous fashion of the Brothers Winchester. If you wanna be a resident of the Supernatural world of glorious ghouls and hotter hotties then you’ve got to know how to dress the game.

Here are some of the rules for looking like you belong to the hunter’s club.

1. The first thing you must have is a jacket. Jackets are a NECESSITY for hanging with the Winchester clan.

They can be leather (and RIP Dean’s leather jacket o’ hotness)

Post-apocalyptic camo flack (and if you don’t think 2014 AU Killer Dean is hot, then you need to just walk away now gurl)

Angelic cotton blend trench (and the bonus? This fabric is so durable that it can survive water, fire, and blood – as well as having a neat compartment for storing your wings)

Or just plain ol’ devilishly delicious green corduroy (and yeah if you notice the similarity between Lucifer Sam fashion and AU 2014 Dean fashion then you win a gold star and a big hug since it means our AU Dean was all woeful and pained.)

No matter what, you must remember to have a jacket at hand to attend the Winchester party. If not, then gurl you are gonna end up out in the cold.

2. The next thing you MUST HAVE are jeans. If you aren’t carrying denim, well then you are really out of the loop.

Your jeans can be can crisp and new

Or they can be ripped and rugged

3. And of course, you can never forget your flannel.

Flannel can be for those days when you are feeling extra manly

Or when you’ll need extra warmth from the cold, cruel world

Flannel is an essential item in the Supernatural closet. Once you have the flannel you have the formula for everyday success because in the America of Supernatural, it is ALWAYS chilly so you must LAYER, LAYER, LAYER. If not? Then you may as well be naked. So ladies (and gents) go to the nearest woodsman store and stock up.

4. The next thing you must own… suits.

The life of a hunter can be sophisticated at times, so you must have career wear on hand.
For those late night visits to the hospital (and isn’t Sam’s hair hot here? I mean, if hair was an accessory we’d so be going there, but that’s for another time dearies.)

And sometimes you need even more formal wear (yes, Sam, even I’m agape at the gorgeousness that is Dean in a tuxedo.)

Career and formal wear are essentials, but they require one thing to make them complete.

5. Always remember to have a white shirt.

And all I can say about Dean in a white shirt? (jaldfjafdioajfdlasjflkdjaklfdjaskljfldajfdioa…dead.)

6. But to go with the white shirts and the formal suits, you should always leave room in your closet for the occasional costume.

For when you are feeling holy and divine

Or when you are feeling hot

Or when you are feeling active

Or when you are feeling nostalgic

Or even more nostalgic

Or when you just feel like letting loose

The point, dear girls and boys, is to make sure that your wardrobe is just as fun as it is serious. We all like costumes every now and then.

7. Now as for accessories….you can never go wrong brightening up the wardrobe with some selected pieces or items. In the world of the Winchesters, you choose your poison.





Or even jewelry

And let us take a moment to mourn it...

You can dress like a Winchester, but no matter the material, the style, or the occasion the fashion sense of Supernatural would not be anything without these two necessities...





# Beverly 2013-04-09 11:11
"No matter what, you must remember to have a jacket at hand to attend the Winchester party. If not, then gurl you are gonna end up out in the cold."

Bookdai - you missed a very important point. If I am invited to a Winchester party, I may "forget" the coat because there are two gentlemen there willing to warm me up. :lol:

Great article to wake up to - love it!!!! The last two pictures are especially yummy.
# suzee51 2013-04-09 12:49
Loved, loved, LOVED this article! Thanks for the giggles and the drooling . . .

Oh, and Bookdal? "For those late night visits to the hospital (and isn’t Sam’s hair hot here?)"

The reason that I didn't notice Sam's hair in that picture was because I couldn't get my eyes away from Dean's shoulders and arms filling out that suit jacket! *sigh*

(Honestly, that man can make anything he wears sexy.)
# elle 2013-04-09 13:03
This was hysterical! So funny. I loved it.
# Sylvie 2013-04-09 14:29
Thanks for the laughs! And might I just add that I fell off my chair with those last two pictures. Hubba, hubba! :oops:
# love2boys 2013-04-09 14:35
Sometimes I can't quite get over the beauty. But - this is why the Impala is bigger on the inside than it is on the outside! Right? All those clothes, immaculate, pressed when needed, in the trunk with the weapons. I love me some Supernatural. Go hair! Go eyelashes!
# lkeke35 2013-04-09 15:00
I loved this article and the wonderful pics that went along with it. It's all beautiful.

Also: nice buttshot of Sam in ripped jeans.

When are you gonna do an article about Sam's hair?
# Alice 2013-04-10 13:40
I'm not sure if you're aware, because we do have a lot of new visitors on this site, but every season I do a feature called "The Enigma of Sam Winchester's Hair." I also do a few occasional hair articles here and there if the episode is exceptional. I believe I did one for "What's New Tiger Mommy?" I'll provide links if you didn't know, otherwise you can find those via search in our archives.
# Bamboo24 2013-04-09 18:02
My own personal opinion, for what it's worth....

Love Dean in blacks, blues, dark greys, and whites.

Love Sam in reds, browns, and dark greens.

Both guys look great in plaid.

Sam looks better in a suit.

# Leah-unlogged 2013-04-09 18:30
I might have to give it to Sam in suits but Dean in tuxedos has the edge IMHO :P
# gunznammo2 2013-04-09 18:06
Those are two beautiful and amazing brothers. Can't get enough! Thank you!

Now we need an article about all the weapons said brothers have in their arsenal. ;-)
# lkeke35 2013-04-10 16:20

Now we need an article about all the weapons said brothers have in their arsenal. ;-)
There is actually a website for the Winchester's weapons: at the IMFDB. The Internet Movie Firearms Database. It's pretty comprehensive up til about season 3.
# eilf 2013-04-09 18:09
I love the greyhound t-shirt - wouldn't care which of them wore it :D (or not, that too)
Far Away Eyes
# Far Away Eyes 2013-04-09 18:43
Squee. That's my first reaction to this lovely piece.

Giggle snort. That's my second.

This made me smile wide and big. You, dear Linda, have just earned yourself a Little Girl Clap.

Love it. And now I know WHAT TO WEAR as opposed to What NOT to Wear.
# judyann 2013-04-09 19:02
What a perfected ending to a beautiful day! Love, Love, Love Dean in white dress shirt and Sam in the green jacket. Escpecially love the last two pictures, could stare at them all day!
Clarice 0909
# Clarice 0909 2013-04-09 20:34
I'm still laughing out loud :D :D :D :oops:
Probably my neighboors are gonna throw me out of this building....
Loved and concur....
The only thing better than a Winchester with all his layers, is both Winchester without any layer whatsoever....

Take care,

Cla; }
# Donna 2013-04-10 00:21
I actually dressed hunter style the entire winter. Now that summer is near I'll switch to Khaleesi style.
# E 2013-04-10 14:47
Lovely! How beautiful are these boys?! You could do an expose on their various ties alone.... I remember thinking how great Sam looked in that grey suit and purple tie in Goodbye Stranger. Did anyone else think that?
# ConKnee 2013-04-10 21:16
I must admit it every time Jared takes off his shirt, I'm like "Jensen Who".
Clarice 0909
# Clarice 0909 2013-04-11 06:59
I must admit it every time Jared takes off his shirt, I'm like "Jensen Who".
Well, my reaction would probably like "Where is shirtless Jensen??? Wanna some Shirtless Jensen time too!!! why not both of the shirtless a whole episode???????"

:o :roll: :lol: :D
# eilf 2013-04-11 09:33
Type 'Jensen Ackles Soccer' into Google Images


you're welcome :D
# ConKnee 2013-04-11 18:13
WoW! In all my time in stalking researching Jensen Ackles I have never seen these picture. A profound thank you.
Clarice 0909
# Clarice 0909 2013-04-11 07:00
I must admit it every time Jared takes off his shirt, I'm like "Jensen Who".
Well, my reaction would probably like "Where is shirtless Jensen??? Wanna some Shirtless Jensen time too!!! why not both of them shirtless a whole episode???????"

:o :roll: :lol: :D
# ConKnee 2013-04-11 18:05
why not both of them shirtless a whole episode???????"

:o :roll: :lol: :D

Why haven't they done that yet?
# ryder21 2013-04-10 21:42
I just love Jensen in a suit and tie. That green tie he was wearing at the beginning of Heart so suited his eyes, and the grey suit and tie at the beginning of FaG was....whew!
Pragmatic Dreamer
# Pragmatic Dreamer 2013-04-11 21:57
A hearty thank you Bookdal.

Joy abounding looking at this, although I shed a tear for the stolen Leather Jacket of Manliness. (If it wasn't so flippant, I would say that stealing that piece of divine apparel was a crime against humanity.)

And I so miss Dean's jewellery. I know the amulet got tied up with other things, but it was such a powerful symbol of all things Winchester. I hope it's found again somewhere - like around Dean's shirtless chest!!!! (Smiling again!)

All in all, and all these pictures makes me long for the good ol' days when a man of a certain standing (they're Men of Letters after all) needed "dressers". Not the wooden drawers type. But a real person who helped the man in and out of his couture.

Hand going up in the air to volunteer for that job now!

I have to say though, I am still longing for the beach episode!!! Maybe as a special treat in season 10?

Yours in dreaming of denim & flannel,

Pragmatic Dreamer :P
# fanotheboyz 2013-04-12 16:54
Thank you. It's cool and rainy here today and I've been having trouble warming up. Not anymore. Fan please?
# debbab 2013-04-13 22:47
Loved your fashion review. New clothing this season so far besides the costumes. Dean in that grey/plain jacket when he interviews the man who saw the burning bush and heard Samandriel. Sam's sweater vest look when he researches the Nazinecromancers.
Can anyone remember when Dean stopped wearing the ring? I know when he tossed the necklace, but cannot remember the ring toss or was it just not continued?
Amruta Karve
# Amruta Karve 2013-04-15 01:12
Where did all the accessories of Dean go?? I mean i know he threw away the "Samulet". That's okay. But why did he stop wearing that awesome ring in his right hand finger and that breslate?? And also how and where Dean's leather jacket got lost?? Did they show it on the show or we are just assuming it got lost in Purgatory i think?? He had it season 7, right?? I don't remember......
# LEAH 2013-04-15 15:11
I believe the leather jacket got stolen (from the set, or on location). I do know that Jensen was not sad to see the amulet go. It was always flying up and bonking him in the face during action/fight scenes. It even chipped his tooth once. As for the other stuff, don't know for sure.
Amruta Karve
# Amruta Karve 2013-04-15 01:16
Those tattoos are the best ever! It's dual purpose..... saves you from getting possessed by demons and has some great design for a tattoo... :lol: