obviously, running with the Winchester's didn't exactly afford you all luxury. Sure, you all took out various credit cards with numerous fake ID's, but charity shop clothes were very often commonplace in your "wardrobe" (a duffle bag)

when you consistently got covered on blood, monster guts and various other liquids or bodily fluids, it was easier to just throw ripped or ruined clothes away and buy brand new ones than to try and clean them — sure, there were the staple items, Deans leather jacket, Sam's Carhartt jacket, leather work boots, a pair of converse that Sam had had since college — but they were one of very few items you ever kept and carried with you.

which is all a long winded way to say that you and the boys had ended up in a thrift store — and they had ended up sitting outside of a fitting room, as you tried on clothes to check if they fit.