Trump may be okay with Elon wearing Dark MAGA hats and t-shirts in the oval, but this is something else
Trump is a vulgarian, but he cares about aesthetics and he cares about how people reflect on him. His taste may be awful, but it's part of his self-image
Tim Pool has neither the social nor financial capital to get away with a beanie and hoodie in the WH. I'll be surprised if Trump puts up with Pool's wardrobe even if Pool is a sycophant on par with Loomer (I almost said suck up, but...)