Ultimately the ventures of AMERIKA HIGHSKOOL is pretty irrelevant on the whole of your life except for local bragging rights if you're ever going to end up being the Highschool star QB that ends up staying behind trying to work blue collar because you somehow suffered too many concussions playing futy-bul. And even then you're likely to outgrow the varsity jacket all the while, I know guys who've managed to outgrow the service uniform or whatever they got for serving the military twenty years ago. Chances are as a whole it's not going to fit.

But at the same time I can understand a sort of emotional want to have one, it's a good thing to show off while it's a culturally significant thing to have.

That said, I'd say just give the jacket to the kid. Saying no in mind just really sort of paints an un-pretty picture of the faculty as a whole. Even if he's doing some extra curricular activity. So he's going beyond his handicaps as sports or band kids go beyond what's expected to be average.