I've never been a big hat wearer myself, tended to like wearing beanies when younger (when I had hair) now not so much, even in winter. I wear cycling caps under my bike helmet so I don't tan like the vents in the helmet, and to prevent sweat down my face since I don't have hair to  soak it up, and also really like bandannas as well also in sport for same reasons

I'm with you Joe, I only wear my furry hat with earflaps when I'm outside below zero. I spend a lot of time shaving my head every day, and I want to show it off! The barber that gave me the headshave yesterday even commented how nice and shiny my head was, and he liked it.