One of Sam’s uglier plaid shirts, in my opinion, (sorry Sam...and Jared, who has worn this to a convention, I believe). It has pointed pocket flaps and is another snap up. Plaid on the shoulders runs diagonal to the rest of the shirt.
Brand Information: American Eagle.
In Sin City (3x04), Sam wears it at the very end of the episode when he talks to Ruby.
Sam wears it while training with Ruby in the summer of 2008, as we see in flashbacks during I Know What You Did Last Summer (4x09).
In After School Special (4x13), Sam wears it to go see Mr. Wyatt at the end of the episode.
In Fallen Idols (5x05), Sam wears it at the beginning of the episode while he and Dean drive to Canton, Ohio.
In All Dogs Go To Heaven (6x08), Sam is wearing this shirt at the beginning of the episode when Crowley meets them at the diner.
In Like A Virgin (6x11), Sam wears this shirt when he joins Dean for the trip to Oregon.
In Let It Bleed (6x21), Sam wears this shirt from the beginning of the episode, until after they summon Balthazar to tell him about Castiel and Crowley and ask for his help.
In Hello, Cruel World (7x02), Sam is wearing this shirt as he sleeps on Bobby’s couch. He wears it throughout his discussion with Dean about his hallucinations (and field stripping his weapons). He changes out of it before they get the news about the swim team deaths.FATE: Unknown
Worn by Jared: March 2008 Salute to Supernatural LA (source)