About T-Shirt Design
You do not have to think too hard about High. Hoodie T-Shirt. The joke is right there and it gets the point across fast. It fits really well with everyday humor, but you do not have to be obsessed with that stuff to enjoy the joke.
You could wear it for casual days, bring it out for holidays, or just keep it in the normal shirt rotation. This is the kind of idea that works well on novelty shirts because you can understand it right away.
The graphic tee style keeps the whole thing casual and easy to understand. The whole point is to get a laugh, and the shirt does that without making things complicated.