He can wear anything he wants. So can you. So can anyone.
If he wants to, and for all I care, he can dress up like a clown. Or dress up like a jester. Or he could wear Gucci or Prada. Or wear steampunk leather outfits like he is in the world of mad max. Or he could go clean cut preppy. He can wear a fedora and a trilby on top of one another.
But, by personal choice and temperament, he wants to dress as he dresses. It just so happens that his personal preference aligns with a particular trope. A particularly uncool trope in popular culture.
I’m pointing out that alignment. I am not making him dress that way and I am not forcing culture to judge him.
It takes a lot less effort to generate your superficial criticism than it takes the GP to reply.
Fortunately, he did reply in a sibling post, but he didn't have to.
I'm not buying this alternative reality where I'm trolling by pushing back on mocking someone's choice of a hat that is one of a limited number of common hat styles.
But why should he not be allowed to wear one? Again, you're policing. It's a discriminatory dick move.