I didn’t realize this til tonight, but Benny never had his hat in purgatory or at his resurrection. He got it afterwards and all I can think of is he and Dean walking down the road to a bus stop and getting some snacks at a gas station. Benny sees the hat and Dean says something about it being dorky so of COURSE Benny buys it and from then on always wears it around Dean to show he can in fact rock it.