I still wear a trilby whenever I'm in the city - and a flat cap in the countryside. I get some good-natured, amused looks from people, doing so at my age. Whenever I meet someone who can remember when men my age still dressed well, it's so cheering to see what it means to them.
I do like pillbox hats, though I think they're a little too discreet. I think berets and brimmed hats go best on women. Kraftie will probably tell me that a beret is a pillbox - somehow.
Given that most people are incapable of driving road cars well (myself included), I hope not.