I have a few flatcaps/ivy caps that I wear every day, unless I'm working or shooting, in which case they may be swapped out for a Guinness ballcap. Then there's the fedora (not a trilby) that my music fraternity wears instead of letters. I prefer the flatcaps even with suits, but the fedora is pretty nice when one needs to look extra classy.
Nice to see others of the same bent. I tend to stand out a bit.