I've been thinking about that too? My assumption was that he got arrested or was involved with a crime scene and got called in for questioning or something, because they all look hella grumpy in the in-character shots. Or maybe that's just the face you make when you're on the subway, idk. But the idea of it being Karen's is ADORABLE, and I love it. You know that if Matt was at her apartment and in need of a shirt for some reason, she'd give him that just for irony's sake.
Re: Matt's NYPD t-shirt