Sam introduces us to a new blue plaid shirt, just in time for it to be destroyed. Not much to say about it – it’s a very dull blue and grey plaid.
In Dark Side of the Moon (5x16), Sam is wearing it when he is shot. He changes out of it after he is resurrected.
FATE: Sam is shot with a shotgun at close range while wearing this shirt, destroying both the front and most likely the back of the shirt:
Possibly Worn By Jared: September 2008 EyeCon Orlando Florida (or it's just a similar shirt...the dates don't really match up, as Jared would have to wear it to the convention years before it appeared in the show) (source).