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8. His gym teacher outfit

It's always a good idea on your birthfday to air out your legs, let them breathe a bit. And what better way than via red, belted shorts? Red, belted shorts! Plus, if he gets cold, Dean can always put on his gym track suit.

There's a little bonus Janitor Sam for you, too. Dean wouldn't be happy if we celebrated his birthday and totally ignored his brother, after all.
7. A Henley


These shirts are just really flattering on him. I think maybe it's the round neckline. Whatever it is, he should really wear them more often. Just look how versatile it is! If it's a little chilly, button up the collar and push the sleeves down. If it's a little warm, pop some buttons and push up the sleeves. It's a win-win situation.
Comments
Time After Time really was a treat for all the hot looks!
I definitely like the slightly longer hair this season too!
That was fantastic! I felt like it was MY birthday. (Oh what a present that would be... To have Dean jump out of my birthday cake.. It ain't the candles raising the temperature! Smokin'...)
But I digress. I love all your splendid sartorial choices. I would add one more - the blue jumpsuit from MTNB. Thud!
However, I must confess -- the slouching against the Impala and the thigh holster get me every time. And the tux. And the 40's gear... Okay, I'm just repeating you.
But, there is one more. If he could just figure out a way to wear a sniper-rifle-po ised-next-to-hi s-face-in-perfe ct-lighting at all times, I would be a happy camper.
And speaking of camping, I say again.. Why, oh why, can't the boys have a summer moment, by a lovely lake, and be wearing nothing but their surf shorts?!! C'mon. They have to hunt near the beach sometimes!
Thanks again!
Pragmatic Dreamer
THE PEARL HANDLE GUN IN THE SHOULDER HOLSTER! OH MY.
SUZEE51, YES I SAW THAT VIDEO, I AM TRYING TO GET THE FULL HOUR WITH THE J'S, & NOT JUST LITTLE CHUNKS OF IT. I CAN GET THE FULL HOUR FROM OTHER CONS BUT NOT CHICON.
HE REALLY MUST DO A LOT OF UPPERBODY STUFF. HIS BICEPS REMINDS ME OF CHRIS PINES FROM STAR TREK & UNSTOPPABLE.
OK I NEED TO GO TAKE MY MEDICINE, MY HEART IS SKIPPING BEATS. THANKS
You’ve made some wonderful choices here.
The canvas jacket, the sweater vest, the Henley(I never knew it had a name), the plaid shirts, the 40’s attire and Dean’s longer hair.
Mind you those that suggested the camping and beach attire works for me too.
Ok I have to go stand out in the snow for a moment.
Thanks for the gorgeous pictures. Is it Feb. 3 yet? We get to see shirtless Dean in that one. Something to look forward to. Shallow, I know.
Although, your number 10 would be my number 1. Just love the cocky Dean in that leather jacket with the upturned collar. So badass!
I'd also add his jewelry back.
Camping with shorts is also a great image to dream of. Hmmmm!
Great pictures, thanks!
Dean looks cool leaning against the Impala, no matter what he is or is not wearing.
Is this list limited to only clothes???
AMULET, where are you???????????
I definitely like the 40's attire the best, but the tux runs a close second!
And speaking of sexy, I just rewatched all of season one and he wears a red shirt in that season. Maybe more like maroon? He looks good in that color too. Really, really good. Did I mention he looks good?
Love your choices. I pretty much welcome anything that shows his shape. The man is just beautiful.