This shirt looks like so many of Dean’s shirts, except for the fact that it has very dark buttons. It also appears to have seams on its breast pockets. The buttons sometimes appear black. This is actually two shirts - exactly the same make, but one is grey and one is green. It is really hard for me to tell which is which all the time, so I've combined them into one entry.
Brand Info: Eddie Bauer
In Swan Song (5x22), Dean wears this shirt from the beginning of the episode until he says goodbye to Bobby after Sam’s death. (grey)
In Live Free or Twi-Hard (6x05), Dean is wearing this shirt as the episode opens. He wears it while they talk to the newest missing girl’s father, but changes out of it before he and Sam go to the Black Rose bar.
In Family Matters (6x07), Dean wears this when they go to the Campbell Compound to check if Samuel has a soul. He keeps it on for the rest of the episode.
In Clap Hands If You Believe (6x09), Dean wears this shirt when he and Sam go to talk with the fairy-lady in her trailer. Presumably, he wears it until he gets out of jail.
In Appointment in Samarra (6x10), Dean wears this shirt for the entire episode.
In ...And Then There Were None (6x16), Dean wears this shirt at the beginning of the episode at Bobby’s, and also when they go to the cannery to hunt the monster.
In My Heart Will Go On (6x17), this may be the shirt that Dean is wearing at the beginning of the episode when the boys are at Bobby’s.
In The Girl Next Door (7x03), Dean wears this shirt from when we join the Winchesters at Rufus’ cabin until the end of the episode, except for a brief scene when Dean talks to the coroner and then phones Bobby from the car.
In The Mentalists (7x07), Dean wears this shirt at the beginning of the episode when he steals the Dodge.
In Adventures in Babysitting (7x11), Dean wears this shirt at the end of the episode when he tries to convince Crissy’s father to stop hunting and then says goodbye to Crissy.
In Party On, Garth (7x18), Dean wears this shirt until they kill the shojo.
In There Will Be Blood (7x22), Dean wears this shirt for the entire episode.
In Survival of the Fittest (7x23), Dean continues to wear this shirt for the entire episode, and thus is sent to Purgatory still wearing it. (green)
In We Need to Talk about Kevin (8x01), Dean returns from purgatory still wearing this shirt at the beginning of the episode. He immediately steals someone’s backpack and changes. We see the shirt in flashbacks of Purgatory as well. (green)
In A Little Slice of Kevin (8x07), we see Dean once again wearing this shirt. Either it did not get nearly as ruined in purgatory as it seemed, or Dean liked it so much he bought more than one. In either case, it’s looking whole and hearty at the beginning of the episode, as Dean spots another thing from Purgatory that he didn’t think he’d ever see again – Cas – while on his way to Rufus’ cabin. He and Sam briefly wear suits on the case after that, but we again see the shirt that evening when Dean is lying in bed with the laptop and thinks he sees Cas outside the window.
In LARP and the Real Girl (8x11), Dean wears this shirt after the case is wrapped up and he and Sam say goodbye to Charlie and then Sam decides they should stay for the Battle of the Kingdoms. (grey version.)
In Everybody Hates Hitler (8x13), Dean wears this shirt at the end of the episode, when he and Sam are back at the Bunker, and Dean brings Sam a glass of whiskey while Sam organizes the library. (grey version).
In Goodbye Stranger (8x17), Dean wears this shirt from when we first see him (the real him) in the bunker taking inventory on some old boxes.
In Freaks and Geeks (8x18), Dean might be wearing this shirt when he and Sam track down Krissy and then meet Victor for the first time.
In The Great Escapist (8x21), fake!Dean wears the grey version of this shirt in his second scene, when Kevin sends fake!Dean and fake!Sam out for food.
In Clip Show (8x22), Dean wears this shirt from the beginning of the episode until they get back from visiting the priest in St. Louis.
In Slumber Party (9x04), Dean wears this shirt from the beginning of the episode until the Wicked Witch is defeated. (grey version).
In Black (10x01), Dean is wearing this shirt on the first day we spend with him and Crowley at the bar. He takes it off only to have sex, and then wears it again until after he kills the demon in a fight.
In Paper Moon (10x04), this might be the shirt that Dean is wearing from the morning that he and Sam sake out Kate’s apartment until the end of the episode.
In The Things They Carried (10x15), Dean has changed into this shirt when they drop Cole off at his friends house and then proceed to follow him to the cabin. He wears it for the remainder of the episode. (grey version)
In Paint It Black (10x16), Dean wears this shirt after his confession when the sister finally comes clean about the ghost in the church and they begin to hunt it. (grey version)
In Angel Heart (10x20), this might be the shirt that Dean is wearing when they see Claire off at the end of the episode.
In The Prisoner (10x22), Dean is wearing this shirt when he arrives in Shreveport. He wears it until the end of the episode. (grey)
In Plush (11x07), Dean wears this shirt after he changes out of his suit and goes to Rita’s house for the second time in order to confront her about the information she withheld about her brother. He keeps it on for the rest of the episode.
FATE: Dean is sent to Purgatory while he is wearing this shirt. So I assume it takes quite the beating.
In The Prisoner (10x22), the shirt gets severely bloodstained while Dean slaughters the entire Styne family. (grey)