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#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??

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This may be the only picture where you can see Sam's trousers. 

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Add the coordinating scarf and pocket square for Sam, and the beaded bracelet for Dean... and, well... 

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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!

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How many of you gasped when Dean woke up in the WWII uniform? Robbie Thompson always knew what the viewers wanted!

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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

15 10 Tap Dancing Dean

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! 

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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. 

15.10 HLC 0356 Dancer Dean

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(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,

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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.

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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. 

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Blue Steel gasp.

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#1  Tuxedos for the Win

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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!"


I know I missed some of the best dressed moments! Help me out and add them in the comments!

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