I favor a dress code for entering the White House. And no hats for men while indoors. He does great work we are told on this thread. Great. But what does that have to do with looking like slacker slob?
It’s a running gag. That is what he wears every day on his podcasts. He must have a dozen of the same in cleaning rotation.
I think he has admitted he suffers from male pattern baldness, so the beany maybe covers the Rogaine or he just thinks the beanie is a better schtick. Too many shaved heads already on the internet. :-)
In this case the attire is akin to a trademark. To see him any other way would likely make him unrecognizable to his audience. So...I’ll give him a pass.