okay well if you're trying to distract yourself pls feel free to provide some thoughts on the topic of Sam's wardrobe specifically his terrible shirts and his reasons for loving them so kindly (or alternatively: Sam and Dean go to the beach and Sam's beachwear is like Jared's bizarre beachwear choices) (... I invite you to tell me more)
I won’t pretend to be able to write good meta/speculation, but I do have several (disorganized, unsubstantiated) thoughts on Sam’s often eccentric fashion choices. My ideas on the subject are deeply connected to both the way Sam and Dean were raised, and to who Sam is as a person, and can be distilled into two possibly contradictory streams of thought:
1) During his childhood, there wasn’t enough room for Sam to have many things of his own, and he was discouraged to a certain point from expressing individuality. Starting when he got to Stanford, he used his clothing as a way to show his individuality, both to himself and others, by literally wearing it on his sleeve. This tendency, IMO, continued into Season 1 (hence the legendary purple dog shirt), but disappeared slowly in the years after that as the course of his life changed and his sense of self was eroded.
2) Sam as a person is highly function-oriented. He isn’t all that interested in luxury. He eats because his body needs it, not because he really enjoys food (and he tries to feed his body only things that will be beneficial to it). He works out because it makes him a more efficient hunter, not to look good or impress anyone (except maybe when he was soulless and fond of doing shirtless chin-ups in motel rooms). I’d imagine his attitude toward clothing is largely the same. A shirt is a shirt. It serves the same purpose as any other item of clothing: to keep him warm and conceal his well-defined chest from our collective lustful gaze. This is my theory on why, for example, the hideous and infamous rusty bacon shirt has made so many appearances. To Sam, plaid is plaid. What the thing looks like is irrelevant.
Anyway, these are my rambly thoughts on Sam’s choice of shirts. Of course, they can probably be easily refuted, since Sam has also done things like grow his hair out and keep it consistently long, despite the impracticality of the style and the frequent resulting jabs from Dean, so he clearly still has personal preferences re: his appearance. But alas, writing meta is not among my strengths. I’d love to write fic on the subject at some point though (possibly involving Sam and Dean and the beach…).