It’s the very visible stitching at the seams that distinguishes this greyish beige shirt from Dean’s S1 grey/tan shirts. It’s got buttons and visible seems. It has two breast pockets that do not have pocket flaps, but do up with little buttons. There are actually too versions of this shirt, a green one and a beige one, but they are very hard for me to tell apart.
Brand Info: Wind River
In Children Shouldn’t Play With Dead Things (2x04), Dean changes into this shirt before they go talk to Angela’s friend Neil for the first time. He changes out of it after they confront Angela’s father for the second time and Sam yells at him. (Note: the shirt appears very grey in this episode – almost green in some shots.)
Dean wears this shirt for the entirety of Born Under a Bad Sign (2x14), only taking it off so that Jo can see to his bullet wound.
In Folsom Prison Blues (2x19), Dean wears this shirt after they escape from the prison.
This might be the shirt Dean wears in Ghostfacers (3x13), for the duration of his time in the Morton House.
In No Rest for the Wicked (3x16), Dean wears it from when they are getting ready to hunt Lilith until the end of the episode...much like Dean, the shirt doesn’t survive.
In Death’s Door (7x10), Dean is wearing this shirt in Bobby’s memory of a movie-night at his place.
Dean must have missed this shirt and bought another one... because, in The Born-Again Identity (7x17), he wears this shirt while at Rufus’ cabin as he tries to find help for Sam.
In I’m No Angel (9x03), Dean wears this shirt at the end of the episode, when they’re all back at the Bunker after successfully finding and rescuing Cas. (beige version).
FATE: Dean gets shot in the left shoulder while wearing this shirt in Born Under a Bad Sign (2x14), yet, the Winchesters amazing blood-stain removal and tailoring skills miraculously resurrect it as though nothing ever happened.
It is completely shredded (not to mention soaked in blood) in No Rest for the Wicked (3x16):
(Note: This is the beige version of the shirt.)
In All Dogs Go To Heaven (6x08), the Skinwalker wears this shirt (presumably given to him by Dean) after Dean and Sam pick him up from the pound. He wears it until he changes into a dog during the fight in the warehouse. Then, presumably, Dean and Sam recover the shirt.
In Remember the Titan’s (8x16), Prometheus wears this shirt. It could, in fact, be an instance of clothes sharing, as Prometheus doesn’t have any belongings of his own, and this appears to be the green version of the shirt (not the beige version that was destroyed by the hell hounds):
If this IS indeed an clothes sharing event, then that means that the back of this shirt gets run through by an arrow when Prometheus kills Zeus. And thus both versions of the shirt are now ruined.