From Suits to Shorts: Dean Winchester’s Most Memorable ‘Supernatural’ Fashion Moments

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Image Courtesy The CW.

What does a priest, a cowboy, and a medieval squire all have in common? Dean Winchester! Over the course of 15 years, Supernatural‘s Dean Winchester has donned a variety of outfits in the name of hunting assorted monsters, demons, and a whole plethora of other beings. With the series now at it’s end, let’s take a look back at some of the most memorable, classic, and sometimes hilarious Dean Winchester outfits throughout the show!

Whole Lotta Uniforms

A lifetime of hunting monsters has meant that the Winchester’s have sported just about every uniform we can think of. That has, of course, brought us some truly wild unique (and hilarious) uniforms!

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Priest Dean

The Winchesters have impersonated some questionable professions, but one that stays at the top of the list is their priest uniforms. It brought us some hilarious moments including Dean’s running into Crowley, who was also dressed as a priest of all things. One that’s often associated with an older person who is much less cheeky, it’s a wonder some of the victims believed Father Dean was actually an agent of the church.

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Kitchen Staffer Complete with Hairnet

Dean in a hairnet is something I would never have thought to include on my Supernatural bingo card, but we got just that in season 9. Undercover at a wellness center, Sam is given the coveted new position as yoga instructor while Dean is relegated to food prep, which would normally make his day except everything in the kitchen is healthy “rabbit” food. It’s hilarious to watch him pout and ends up being a good thing when he sneaks a taste of the pudding and thereby uncovers how people are being drugged and subsequently drained of all their fat!


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First as a childhood trauma counselor and then as a CPS worker, we got two episodes of Dean sporting the most glorious cardigans ever to grace the show. They just look so warm and comfortable, it makes you want to steal them and snuggle up with a hot cup of coffee. It’s a shame we didn’t get more of Dean rocking his cardigans.

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Texas Ranger 

Arguably one of the best undercover looks of the show, Dean dons a cowboy hat and boots to pass as law enforcement in none other than Dodge City, Kansas. His love for all things western are well established, so it’s fun to watch him get excited for this case as well as force Cas to wear a hat. The bolo tie really completes the outfit and the whole episode is filled with delightfully hilarious western references that make it a fun and lighthearted one fans will always remember.

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Coach Winchester

Of course we can’t have a list of Dean’s most memorable (and outrageous) outfits without including the Coach Dean uniform from season 4. From the headband to the socks, the whole outfit has you shaking your head and Dean’s dedication to the job. You can’t help but laugh at his “The whistle makes me their god” line and well, every single moment he’s on screen. This one is not a uniforms fans will likely be forgetting soon.

A Ramblin’ Man

The classic Dean Winchester look has evolved over the 15 years that we’ve watched him, but some staples have stuck with us from the moment they appeared on our screens.

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Dean’s Leather Jacket

When we think of the early days of Supernatural we almost always think of Dean sporting his (John’s) leather jacket. It was a look that we were sad to see go, but one that will forever remain in our hearts as one of the classic Dean Winchester looks.

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Plaid All Day Every Day

If there is one thing the Winchester’s have in their closet it’s plaid and flannels and plaid flannels. Dean wears an impressive variety of the pattern, so much so that everyone knows if you want to “dress like a Winchester” you just throw on a plaid button up and you’re basically there.

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The Red Shirt

Dean usually dresses in muted earth tones like browns and greens so when he’s in this red shirt, fans sat up and took notice. It’s best known from Dean’s time as a demon, red of course symbolizing his demon status, but we do see it a few more times after that and we’d just like to send a personal thank you to the wardrobe department for each and every one.

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Dean’s Green Jacket

After the leather jacket disappeared Dean when through a few different jackets before landing on the green army jacket that we see him wear often in later seasons. They aren’t exactly the same from season to season of course, but from season 7 onward he dons some variation of a green army jacket right up to season 15. It seems Dean found his perfect color (after all, it does match his eyes!)

Everyone’s Crazy ‘Bout a Sharp Dressed Man

We’ve been graced with Mr. Dean Winchester in a variety of suits throughout the years. Formal tux and bowtie, two piece suits with stylish overcoat, three-piece beauties, you get the picture.

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Suit and Bowtie

The suit might be there go to when it comes to undercover work as FBI agents, but for fancier occasions like casing a high class party for occult objects, Dean was forced into a bow tie and suit combo by Bela in season 2. Is it just us or does he give off James Bond vibes? Not everyone can pull of the bow tie but Dean is among those who can, and should, wear it often.

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1940’s Dean

When Dean gets thrown back in time he teams up with famed hunter Eliot Ness, who thankfully demands Dean be dressed appropriately for the times. This lands him in the hands of tailor Ezra Moore, who turns out a Dean so impeccably stylish even Dean admits in the mirror that he looks awesome.

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FBI Suit

We see Dean in suits quite often while working cases as an FBI agent or some other agency employee, but in the later years of the show he adds a fitted coat that really kicks the whole look up a notch!

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Ok yes, technically this isn’t Dean, but we couldn’t have a list of Dean’s greatest looks without including the angel. For all his faults, what with wanting to destroy the planet, he had impeccable style. He could have chosen a more battlefield ready look but instead he opted for a tailored three-piece suit complete with pocket watch, overcoat, and cap, proving he knows what looks good on his vessel.

A Touch Too Much

Lastly we hit on those outfits that are so over the top they fall into a category all their own. The beauty of this show is it’s creative range that has brought us some truly unique Dean outfits that we can’t forget. Are they too much or just enough?

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Dean never passes up the opportunity to don a costume, so it’s no surprise that when Charlie demands he dress in character for her LARP kingdom he readily agrees. Dressed to the nines as her handmaiden, he escorts her as they work to uncover what is killing off her fellow LARPers. If the episode isn’t amazing enough, the final shot of Dean giving a rousing speech (stolen from Braveheart) to bolster their troops with a long flowing wig and face paint is really the cherry on top!

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Those Purple PJs

I mean, what words can do justice to the hilarious shot of Dean in that purple nightgown and cap running down the hall, or him casually seated on the table as Sam just shakes his head. In this moment, we were all Sam Winchester slightly exasperated but mostly amused at Dean’s antics.

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Frontierland Sherriff 

Dean shows up to the wild west dressed for… well according to the locals, not the wild west. They make fun of his serape and his too clean appearance from the second he arrives. However when things go south for the local sheriff, Dean inherits the title and receives an upgraded wild west Sheriff look that leads to a duel at high noon. It’s a little cheesy, sure, but we’ll take any excuse to watch Dean geek out over his love for all things western!

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Tap dancing Dean

Just when we thought we had seen all there was to see on Supernatural, the writers come up with one more over the top idea: Dean tap dancing during a dental procedure dream. It doesn’t matter how many times you watch that scene; you come away wondering how Jensen is good at literally everything and smiling so big your face hurts. Somehow it worked and Dean looks perfectly at home styled in the classic outfits we see in old black and white films.

I hope you enjoyed our little journey of Dean’s most memorable outfits over Supernatural‘s amazing 15 year run. We’re going to miss his classic Dean style as well as his undercover and sometimes over the top wardrobe selections. Which outfit was your favorite? Let us know in the comments below!

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By Brianna
Brianna works full time in the publishing industry, passionately building books to bring to the masses. Her first fandom was Harry Potter, which she joined at age 11. Her love for books took her abroad to earn her Masters Degree at University College London, after which she lived in New York City, and now resides in Austin. She loves all things fandom including Supernatural, Doctor Who, and more. Ever the introvert, she can usually be found reading, playing with her dog, listening to music and practicing yoga. Brianna joined the Nerds and Beyond staff in 2018 where she unites her love for all things "nerd" with her passion for writing. Find her on Twitter here: @bookbag09
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