My serious answer is no. He does not need to lose the hat. It makes him feel special or something or whatever, so he can wear it if he wants. There's no harm in wearing something dumb if it makes you happy.
My not-so-serious answer is... God damn, kid! The other kids are going to start making fun of you something fierce if you keep wearing your dad's fucking police hat... You're like sixteen... Can you imagine going to high school with a kid like that? Who wears his dad's sheriff hat? People would be so mean to him... One of the other kids should start wearing their parent's fireman hat. I'd personally like to wear a silly sailor hat. Neither of my parents are/were sailors, but sailor hats are fun... and hey, my user-name is Gilligan, so it would be fitting. Then maybe I can spend some time shoved into the locker next to the one Carl will be shoved into.
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