Dean is really starting to like grey/charcoal plaids. This particular plaid shirt looks like it might be a cotton flannel shirt, as it looks pretty thick and cozy. It has dark and light greys making up the plaid, with thin double red lines running through it. It does up with brass-coloured buttons.
Brand: Abercrombie and Fitch
In Devil’s Bargain (13x13), Dean wears this shirt when they track Lucifer and Anael down to the motel that they’re staying in.
In Beat the Devil (13x21), Dean wears this shirt after Gabriel and Rowena have captured Lucifer, and they’re able to use his grace to open a door to the alternate world. He wears this shirt until the end of the episode.
In Exodus (13x22), Dean wears this shirt for the entire episode.