In college someone asked me why I never wore a hat. The question caught me flatfooted. I had no answer at the time.
I don't wear a hat all that often, mostly because I can't get them to stay on my head. One stiff breeze and off they go. I think that the average hat size is just a wee bit too small for me. I have a fedora that I sometimes wear to work when it's raining, but then I hang it on my monitor stand and as often as not I forget to wear it home.
Maybe I'd try harder to find a hat that fit, if I didn't have a full head of hair. I rarely cut it, mostly because I'd rather wear it long, but also because I never know from one play to the next what my character will be.
When I performed in 1776 a couple of years ago, I was cast as Stephen Hopkins, oldest member of Congress. I bleached my hair white. That looked very odd when it started to grow out. And it was a lot of trouble - next time I think I'll just wear a wig.