Dean really likes greys and greens – I guess they bring out his eyes. This shirt is a little worn at the collar, but that can only be seen in close-ups. Its breast pockets have a slight point to the flaps, and they do up with buttons.
Brand Info: Dickies
In Children Shouldn’t Play With Dead Things (2x04), Dean wears this shirt while he and Sam discuss how to kill a zombie until after they kill (and rebury) Angela Mason.
In The Usual Suspects (2x07), Dean wears it for the entire episode except when he and Sam are at the coffee shop.
In Houses of the Holy (2x13), Dean wears it after the second murder shown in the episode, until the end of the episode.
In Tall Tales (2x15), Dean wears it when he and Sam (and Bobby) go after the Trickster at the end of the episode.
In Heart (2x17), Dean wears it from the beginning of the episode until he kills Glen.
In Dream A Little Dream Of Me (3x10), Dean is wearing it when Sam shows up at Bobby’s hospital room with the information about the dream root. Dean keeps the shirt on until Bobby wakes up.
In Long Distance Call (3x14), Dean wears it the day after he gets his instructions from “John” until the end of the episode.
In Lazarus Rising (4x01), Dean has been buried in this shirt – though it has lost all its buttons somehow. After digging himself out of the grave, he ties the shirt around his waist on the way to the gas-station. He uses it to break a window, and then puts it back on. He changes out of it after he’s convinced Bobby that he’s not a monster or a demon.
It’s a Halloween miracle when in It’s The Great Pumpkin, Sam Winchester (4x07), Dean wears this shirt and it’s been all cleaned up and all its buttons have been replaced. He is wearing it when he arrives at the motel eating candy, and Sam tells him about the contents of the hex bags. He wears a suit to check out the second murder scene, and then changes back into this shirt when doing research afterwards.
In Death Takes a Holiday (4x15), Dean wears it from when they interview the shooting victim, until the failed séance in the graveyard.
In Lucifer Rising (4x22), Dean wears it for the entire episode.
In I Believe The Children Are Our Future (5x06), Dean wears it when he and Sam test out the joy-buzzer on the ham and then go to the joke shop.
In Changing Channels (5x08), Dean wears it when he is in the sitcom.
In The Real Ghostbusters (5x09), this MIGHT be the shirt Dean is wearing from the beginning of the episode until the ghosts are destroyed.
In Unforgiven (6x13), Dean is wearing this shirt at the end of the episode as he and Sam are packing up, and Sam collapses.
In Mannequin 3: The Reckoning (6x14), Dean is still wearing this shirt, of course, as the episode opens and Sam comes to. He keeps it on as they leave town, stop for food, and Dean finds their next job.
In Defending Your Life (7x04), Dean wears this shirt once he changes out of his suit from the beginning of the episode. He wears it until Sam tells him to suit back up so they can go check out the second murder victim (the guy who was attacked by a ghost dog).
In Slash Fiction (7x06), this may be the shirt that Dean wears from when he arrives at Frank’s house until the leviathan doppelgangers are dispatched.
In Repo Man (7x15), this may be the shirt that Dean is wearing from when he and Sam jump Jeffrey in the alley until the end of the episode.
Other Appearances: Some people believe that this is the same shirt that John wore, and subsequently died in, in In My Time of Dying (2x01), which would mean it is also the shirt his soul is seen wearing in All Hell Breaks Loose Part 2 (2x22) - and possibly also the shirt he wore in Salvation (1x21) and Devil's Trap (1x22). I can't confirm or refute this. I never believed it was the same shirt, but then, I have to admit that it is very similar looking and I really don't have enough evidence to prove anything one way or the other.
FATE: In Lazarus Rising (4x01), Dean digs himself out of the grave while wearing this shirt. Somewhere along the way, it loses all of its buttons:
Yet, once again the Great Hidden Tailoring Talent of the Winchesters resurfaces and the shirt also resurrected good as new in It’s the Great Pumpkin Sam Winchester (4x07).