would jon actually go out and about in cool/gnc outfits? probably not, at least not when we know him, as he starts off horrifically insecure about being taken seriously in a way that doesn’t lend itself to allowing one to wear cool outfits, and after that his clothing concerns likely become largely “what would present the least hindrance were I to get kidnapped while wearing it?” which, again, doesn’t leave a lot of room for fun. what I do believe with my whole heart is that he inherited a certain amount of expensive jewelry and clothing from his mother and grandmother that he wouldn’t have felt right getting rid of, and, every so often, if he’s “bored,” he will decide to “play a bit of dress up” “for fun” and end up feeling a profound ache so deep in his chest that he thinks he might need to take the entire next week off work just to process it. and then he pointedly pretends that never happened.