In Part 1 of "Supernatural Top 10 Best and Worst Dressed Characters", I ranked the top 5 worst wardrobe choices in the history of Supernatural. From the heavenly host to the gods above, we proved that supernatural beings may be all powerful but they certainly don't always know how to dress.
It's always better to be positive than negative, though, so let's double that number when looking for the BEST dressed characters in Supernatural! Actually, it was fairly easy to think of outfits that made a lasting, good impression throughout the years. Turn your mind's filter to 'clothing mode' and let the images pop up randomly. See? You probably thought of many of the same fashionistas I remembered... but then again, maybe you came up with a lot more!
So, think of the 10 BEST outfits worn on Supernatural. Witch, demon, hunter, angel, or victim about to die, who were smartest dressers from the past 15 years? Which outfits really stood out for you? Prepare your lists before reading mine. I'll wait....
You're back! Okay, let's get started!
Supernatural's Fashion Forward Hall of Fame
Honorable Mention: Yoga Instructor Sam - 9.13 "The Purge"
ALWAYS a win, muscle-clad Sam in a tank top and shorts. Showing off one's buffed physique while working out is one of the best reasons in the world to go to the gym! 
Look at that beautiful landscaping outside the spa! What? You didn't notice the plush greenery? Yeah, I totally understand.
Honorable Mention: Medieval Sam, Dean and Charlie - "LARP and the Real Girl" 8.11
Admit it These costumes make you smile. Just looking at them, you know people are having fun. 
These guys are joyful, carefree and living in their dream world - if only for an hour or two.
Charlie doubled down by looking fabulous in the best medieval warrior garb ever fashioned for a reigning queen...
while also enjoying the splendor of her court.
#10 Vacationing Amara - 15.02 "Raising Hell"
Nothing says independent, confident woman like a mustard yellow pant suit!
Talk about making an impression! This outfit took command of the room (and any pesky godlike brothers) as soon as Amara emerged from her boudoir. 
An animal print blouse, multiple rings on every finger, and look at those earrings! Is that green nail polish? This woman's fashion is saying everything she wants to say to her brother, and then some! You go girl!
#9 Cowboy Sam and Dean - 6.18 "Frontierland"
Is it the Stetson hats or the leather vest? Maybe we just like the idea of Sam and Dean as cowboys?
Or maybe we want to live in a town where Sherriff Dean keeps the peace... 
and dreamy eyed Sam rides his horse up to the fence of our Ponderosa ranch house. 
I'm not sure where fantasy ends and fashion begins, but these outfits work well on these boys!
#8 Billie as Death
You know, there was nothing special about Billie's outfit. It was simply a black tee (or body suit) and black jeans, but those pieces alone, fitted skin tight, let you know she was woman/reaper/entity you didn't want to cross.
13.05 "Advanced Thanatology"
The full length black leather coat and black gloves simply put the exclamation mark on the statement that she was the new supreme master of Death. 
13.05 "Advanced Thanatology"
Striking a pose in black on black says don't mess with me in so many ways. 
13.19 "Funeralia"
Understated and powerful. That was perfect Billie.
#7 Rowena's Gowns
Even in the depths of Hell (or Hell adjacent hideout), Rowena wouldn't be found dead in anything other than the most stylish dress.
10.17 "Inside Man"
While not above using her feminine wiles to lure her marks, seduce her co-conspirators, or distract her intended victims (when on the occasional assassination mission), it never appeared that Rowena used her clothing as weapons. They always seemed to be a genuine extension of her personality. 
10.17 "Inside Man"
Is that a shawl over her dress, or a part of the dress? I wish I could get infinity scarves to lay that perfectly on me. 
10.17 "Inside Man"
Look at that cloak! While it may be the expected overgarment of a witch of a bygone Scotland, it's dramatic nonetheless.
Rowena as a socialite was never a disappointment, either. From the front, side and back, her gowns were the height of fashion. 
13.19 "Funeralia"
Ironically, her last dress on Earth was not a favorite of mine. I was all for the color but the satin draping and elastic cuffs were a cross between high school musical and Amara's hand-me-downs (See Supernatural's Worst Dressed Characters). The overall impression Rowena left, however, was class through and through. What were your favorite gowns from Rowena's closet?
#6 Samifer
The jaw-dropping impact when Sam appeared in that all white suit was enough to secure Samifer a place in our fashion hall of fame.
5.04 "The End"
It almost appears as if Sam's shirt is a cream color in these shots, but I've never noticed that on my television. I just remember white did not stand for the good guys, and being terrified by the menace hidden behind the suit color's undeserved, feigned innocence. 
5.04 "The End"
Ten years later, the same white suit carried the same message of doom for Dean.
15.05 "Proverbs 17.3"
Messaging through clothing at its best.
Click "Next" to see the Top 5 Best Dressed Characters!
#5 Trust Fund Sam and Dean - 15.13 "Destiny's Child"
Be honest. What first drew your attention: Sam's man bun, his all plum colored suit, Dean's suede jacket, his braided belt.... or the car they were driving??
This may be the only picture where you can see Sam's trousers. 
Add the coordinating scarf and pocket square for Sam, and the beaded bracelet for Dean... and, well... 
we have the exact same reaction as Dean!
#4 Dean in Uniform - 8.20 "Pac Man Fever"
They say there's something about a guy in uniform. Based on this episode, I'd say they're right!
How many of you gasped when Dean woke up in the WWII uniform? Robbie Thompson always knew what the viewers wanted!
Anyone care to take a crack at all those decorations and insignias?
#3 Fred Astaire Dean - 15.10 "The Heroes' Journey"
Who would ever have guessed that we'd get a tap dancing Dean in Supernatural? 
Dean said there was no singing in Supernatural (a rule which Jensen also broke in season 15) but he never said Fred Astaire or Gene Kelly couldn't make a guest appearance! 
White satin lapels, hat, bow tie and tuxedo stud buttons set the stage for a performance that left us all smiling with delight. Anything other that that classic movie attire would have lessened the iconic nature of this 1.5 minute scene that we'll never forget. 
(Alice posted the video clip of Dean's Dance number if you want to see it again!)
#2 Buttoned Down Dean
From the moment Dean put on that period appropriate clothing in 7.12 "Time after Time", he knew he looked goooood!
With the full 3-piece suit...
with the jacket off...
or with an extra layer added...
from head to toe, 
Dean made a mighty fine Treasury agent! 
Michael reprised that sharply tailored, collar bar shirt plus overcoat classic on Dean in the season 13 finale and season 14 premiere.
14.01 "Stranger in a Strange Land"
Michael's style switched out the tommy gun for a pocket watch, and the fedora hat for a cap, but the impact was the same. 
Blue Steel gasp.
#1 Tuxedos for the Win
3.06 "Red Sky at Morning"
What can I say but...
"they come runnin' just as fast as they can
'cause every girl crazy 'bout a sharp-dressed man!"
Phew!
I know I missed some of the best dressed moments! Help me out and add them in the comments!
Enjoy more Top Ten Highlights of Supernatural, including Best (and Worst) episodes, running comedy bits, creepy kids, grossest scenes, classic rock scenes and so much more!
Browse Nightsky's serious and not-so-serious Supernatural commentary on her Writer's Page!
New Screencaps courtesy of http://www.homeofthenutty.com/supernatural