Funnily enough, Supernatural’s protagonists are linked with flannel shirts more than any other apparel. This comes down to the later seasons’ liking for Sam and Dean to wear such garments, although they’ve also been clad in a number of other clothes.
Dean isn’t the biggest fan of fashion, yet the guy does have good choices in a number of styles. True to his character, he’s also been seen in weird and even hilarious clothes. With fifteen years worth of seasons from Supernatural, there were bound to be some hits and misses. Let’s see which ones of Dean’s outfits made it to the list.
Worst: Gym Teacher Outfit
It goes without saying that Dean is responsible for all of the funniest episodes in the series. This particular one wasn’t as funny as you’d think, but Dean did have a hilarious bit coaching the school’s basketball team after being hired as the gym teacher.
While it’s certainly a fun segment, Dean’s outfit is a travesty. He looks like a rejected athlete who still can’t comprehend why people can’t take him seriously. Easily making things worse are his socks pulled up all the to his knees, which has the effect of bringing focus on those very red shorts.
Best: 1950s Inspired Suit
When it comes to dressing sense, the angels have had some wins and some misses. Alternate Michael may have been a bad dude, but the guy certainly knew how to make Dean look like a million bucks. As part of his first act of using Dean as a vessel, Michael got him clad in a 1950s suit.
Despite the look being out of style about 60-70 years ago, Dean certainly brought it back and then some. This style evokes a sense of class you wouldn’t expect from Dean, yet instantly makes any guy want to get a similar ensemble to look as classy as Dean does.
Worst: Nightgown
The history of Supernatural is filled with memes dedicated to it. This is mainly possible due to the antics of the characters themselves, and Dean’s nightgown is definitely going to get memed out as well. That doesn’t mean it’s a flattering look, though.
First of all, the color is what makes one wretch in disgust since it’s so in-your-face in appearance. Then there’s the fact that there are no pajamas, meaning, like Sam, a person is inclined to avert their eyes once Dean sits nearby.
Best: Tuxedo
Whenever Dean is wearing a suit you can be certain he’s not going to be too happy about it. Maybe it’s one of the angels’ powers to make their vessel look dapper if they want to, as this tuxedo was Alternate Michael’s doing.
Dean himself had worn a tuxedo once before and looked superb both times. The winning quality of this tuxedo has to be how it’s so form-fitting, in that Dean has a very edgy appearance that isn’t hindered by a needlessly billowing coat.
Worst: Red Flannel Shirt
This isn’t as bad you might think, it’s just that Dean was far too old to be wearing such a style by this point. This look would suit a guy in his early-20s, not a man who was in his late-30s by this point. For a tough guy like Dean, the flannel also seems too casual.
Dean is better off in leather-bound clothes that aren’t so “neat” in appearance. He also got much burlier later in life and the flannel is better suited to the younger Dean who was far leaner.
Best: Demon Dean's Rolled Up All-Black Combo
Darker colors have always suited the Winchester brothers. It almost doesn’t matter what they’re wearing as long the color scheme is on the dark side, and Dean went with an all-black combo that was an absolute winner in style.
Making it better was his choice of rolling the sleeves up, as they had the effect of going with his cleaner, combed hairdo. The shirt in the inner layer might have clashed had it been a lighter color, so kudos to Dean for opting for a black one. Demon Dean might have done a lot of bad things but he was an ace in appearance.
Worst: Half-Sleeved Formal Look
If you’re ever looking for films and shows starring the Supernatural cast, then be sure to check out Batman: Under the Red Hood. Jensen Ackles played the Red Hood and Supernatural fans got to see Dean interact with a figurine of the character.
Unfortunately, Dean looked way too much like a geek for this crossover to seem cool. The problem was wearing a half-sleeved shirt which never looks good on anyone. Not to mention wearing a tie in a buttoned-up shirt and this was setting up Dean to be a total nerd both in his attitude and appearance.
Best: Additional Brown Jacket Layer
Everybody knows that it wouldn’t be Supernatural if the guys weren’t wearing a bunch of layers in their apparel. Dean took it to another level by wearing this brown jacket, making it three articles of clothing. Well, nobody’s complaining about it.
After all, it made him look a total badass, what with Dean also holding the weapon that was going to kill Dick Roman. This jacket was well complemented by the contrasting shirts underneath. Plus, points go to Dean for carrying himself like a man on a mission.
Worst: Cowboy Outfit
Chances are, you’ll find boys in kindergarten running around looking Dean does here. Rather than keep it simple like Sam, he opted for the full wannabe cowboy appearance that is just laughable. It wouldn’t even have been that had that weird line not been dangling out of his hat.
Maybe the vest wouldn’t have made him seem so juvenile if he hadn’t been wearing a buttoned-up shirt underneath. Whatever it might be, Dean looks nothing like John Wayne or Clint Eastwood, but more like a kid who’s forgotten he’s a fully grown man now.
Best: V-Neck Black T-Shirt
It’s most likely that this image of Dean pops up in your mind whenever you think of him. This is because this looks makes up one of the many reasons why Dean is such a cool character. It’s a simple look, yet one that gives Dean that oomph factor of a protagonist.
The shirt is form-fitting and the V-neck allows for Dean’s intimidating and impressive frame to stand out. The rope of his amulet becomes prominent due to this shirt and there’s no way it would have come across as impressive as it does, had it not been the black scheme that you’re looking at.