Here's your assignment: Think of the 5 most outrageously bad clothing choices donned during a Supernatural episode. The eye-catching attire could have been on a guest or recurring star, or a regular character, but it has to be something so awful, the mere sight of it threw you out of the scene! To be clear, this isn't meant to insult Supernatural's wardrobe department. Most of the time they got it right! But in 15 years, 327 episodes, you have to allow that there were a few times when they may have been rushed, or gotten bad cues from a director, or didn't have budget to run to the fabric store!
Then think of the 5 BEST outfits worn on the show. Witch, demon, hunter, angel or victim about to die, who was smartest dresser on Supernatural? Prepare your lists before reading mine. I'll wait....
You're back! Okay, let's get started!
Supernatural's Fashion Faux-Pas
Honorable Mention: 3+ Layers of Hunter Cotton
You can't begrudge the boys their comfort. Wearing a t-shirt, button down plaid and a jacket is reasonable... but would it have killed them to do a job in the southern states in the summertime at some point? 
I'm not saying their outfits weren't practical and perfectly appropriate for their career choices. Even rolled up into duffle bags, their clothes always looked the same. So, good on them for stretching their shopping budgets. 
It just would have been nice to have gotten the t-shirts alone to show off those hunter muscles - at least once in a while. Real Fan Challenge: Did the boys ever wear 4+ layers?
#5 Castiel's Trench Coat - Seasons 9 to 13
Castiel's best known trademark is probably his trench coat. Complete with a business suit, white shirt and blue tie, our favorite angel's clothing was nothing if not predictable. As he was a solider first, the trench coat became his human vessel's socially awkward, aesthetically oblivious "uniform." His first trench coat, worn in seasons 4 through 8, was fairly smart looking, if one overlooked the frequent wrinkles. Personally, I'm partial to the light tan variation in men's coats. It was also longer in length, with wrist and waist ties. It won't make my "Best Dressed" list, but it worked well as Castiel's travel clothes for his increasingly frequent trips to Earth.
Sadly, Castiel transitioned to a different, far less attractive coat in 9.10 "Road Trip." 
Its dark tan/light brown color didn't do anything to compliment Castiel's blue eyes. It also had no styling whatsoever. Castiel's last appearance in this boring, nondescript garment was during his negotiation for his release from the Empty Entity in 13.04 "The Big Empty." 
Castiel's successful return to Earth was celebrated with the gift of a new trench coat. It wasn't a great improvement, but at least it had some style, so we'll call that a win. 
#4 Death's Skirt - 15.19 "Inherit the Earth"
Admittedly, Billie's commanding presence as Death is a really tough act to follow. Her all black leather ensemble, first seen looming over Dean at the top of a staircase, was one of the best entrances in the series. Before her, Julian Richings' black suit with black overcoat may have been simple but it was perfect for his understated menace befitting an ancient force of the universe. After those two masters of intimidation, the green pleated skirt on the last incarnation of Death was laughable.
Can you think of any historical, artistic or canonical reference that could have inspired that school girl outfit? Truly, I'm at a loss. 
#3 Naomi/Angels' Pant Suit - Season 8
8.10 "Torn and Frayed"
Presumably fashioned to portray angels in Heaven as up-tight, traditional and boring, the female angels' gray "power suit" went above and beyond its original objective. As a uniform that communicated no individuality, the pant suit also proved that the gender neutral angels had no sense of style or fit. Rank had no privileges either, as Naomi's wardrobe was the worst. Her blazer was proportioned too short for her enviably tall stature, making it look too small on her from both the front... 
and the back. 
8.19 "Taxi Driver"
The sleeves, the back flaps - everything about it looked like is shrank after too many trips to the dry cleaners. She always wore it buttoned (to portray Naomi's all-business-no-fun attitude) but the gaps just made it look ill-fitting. 
8.19 "Taxi Driver"
The other women in the garrison weren't any better off. The mere sight of the angel squad, clad in ill-fitting gray and white button-downs, made them instantly unlikeable - so I guess job well done by wardrobe! 
8.23 "Sacrifice"
Moral of the story: Even when you go to Heaven, you won't have anything to wear!
#2 Calliope's Dress - 10.05 "Fan Fiction"
One of my top five favorite episodes of Supernatural happens to have one of my top five least favorite wardrobe choices of all time. Calliope, the Greek Goddess Muse of Eloquence and Epic Poetry, was the villain of the week but the real monster to be slain was her dress.
That dress immediately pulled my attention out of the otherwise beautifully sensitive, sentimental 200th episode. The signature flowers that tipped Sam off to his adversary's identity creeped me out. They looked like bugs (or maybe butterflies?), that swarmed onto the dress and where working their way up to envelop the person inside it. The puckered bustline, 
and the bat wings that formed the cape,
screamed high school production costume department. Maybe that was the intent? Calliope manifested to watch a high school play so maybe her gown was supposed to mimic the art she was inspiring? My image of a Greek muse's attire is more flowing, luxurious satin or silk, as envisioned in these classic portrayals. 
(Reproductions shown on FilmDaily.com; GreekLegendsandMyths.com; and Theoi.com. Sorry, I didn't look up the original painter/ sculptor credits.)
As you can see from the quickie Greek mythology research, aspects of Calliope's appearance were authentic, such as the arm band and the high waisted gathering.
Credit must also be given for providing Calliope with a fully clothed bustline, which was conspicuously missing from several Greek depictions of the goddess. Still, the makeshift quality of the dress will forever be a cringe-worthy blooper in this epic episode. I'm have always been so distracted by Calliope's calamity, I never before saw that the actress who played the part was really quite attractive. 
But that dress! I've never been so happy to have a goddess disappear!
#1 Amara's Black Dress - Season 11
11.23 "Alpha and Omega"
Seriously. The Goddess of all Darkness, God's sister, the matriarch of all time and space, can't do better than a Simplicity pattern, slip-on, cotton (or maybe it's polyester) dress? The seams even puckered! 
11.21 "All in the Family" (this shot almost makes it look like a jersey)
The judges on Project Runway would have sent a contestant packing if they even tried to present that garment as a finished product!
The bodice also varied from the seemingly pinned, straight seam shown in the season finale (first photo above) to what looked like a v-seam when a plunging neckline was needed to distract hapless angels...
11.10 "The Devil's in the Details"
or humans...
11.13 "Love Hurts"
or viewers.
11.09 "Oh Brother, Where Art Thou"
It distracted me sure enough, but not for the reasons they wanted.
I yelled at the television every time I saw that dress. Poor Emily Swallow! You'd think God's sister would deserve to look, I don't know, powerful? Well fitted? I realize she had been locked up for a millennia but the wardrobe choice threw me out of her scenes all season long. Talk about a Queer Eye for the Straight Guy emergency!
Hopefully, this little red carpet commentary on Supernatural's wardrobe disasters made you laugh a little. Now I want to see your picks! What makes you cringe every time it appears on your screen? Have fun, get those "Best Dressed" lists ready, then keep going with Supernatural's Top 10 Best Dressed Characters!
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
Castiel's trench coat researched on http://www.supernaturalwiki.com
