Does your guy live in caps? Mine sure does, I don't know if its because his hair is receding or because, they look cool. Whatever it is, I think he will dig the one I just picked out for him! Check out the Dallas Cowboy NFL Hat that will fit him so well. He likes the adjustable back so, I was sure that it had it going on before I bought it! I might just go and order some more NFL Apparel for him if he's a good boy!