I think he's shooting for "cool dude ballplayer," along the lines of Clayton Kershaw or Bryce Harper. Come to think of it, the person I really need to answer this question is Clayton Kershaw. Dude's got a straight-up coiffure, and I don't think I've ever seen his hat come off.
Yeah, my wife brought up the possibility of the "back-at-ya." Hopefully he won't need that to fix it. I told him he needs to figure out something that works before this weekend. Anyway, I knew there had to be other parents out there who experienced this, just because I see too many kids doing the same thing.