This shirt is quite nice, I think. It’s a bold horizontal stripe, and similar in style to Sam’s Green & Blue Camping Blanket Shirt, so I’m naming it the same. It does up with buttons. It has two flapless breast pockets that also do up with buttons.
In Don’t Call Me Shurley (11x20), Dean wears this shirt at the beginning of the episode, when he is doing the ironing.