Dean picks up a new plaid shirt when he and Sam go to Chicago. It’s a beige and brown plaid with an emphasis on the vertical brown stripes. It’s got breast pockets and does up with white buttons.
Brand: Denver Hayes
Dean wears it for the entire episode of Bloodlines (9x20).
Dean wears it again for the entire episode of Ask Jeeves (10x06)
In Halt & Catch Fire (10x13), Dean wears this shirt at the end of the episode when they drop Delilah off at the widow’s house to make amends.
In Into the Mystic (11x11), Dean wears this shirt while they guard Mildred and wait for the banshee to strike.
In The Chitters (11x19), Dean wears this shirt when he changes out of his suit and heads into the woods to try to find Libby, and first encounters Cesar and Jesse.
In The Raid (12x14), Dean continues to wear this shirt as he continues his argument with Mary in the opening Winchester scene of the episode.