I go back and forth between wanting to and not.
I'm drawing a lot of inspiration from the '20s and '50s now (often directly, by buying vintage clothes), and sometimes I really think that hats would add a lot to the look, and other times I feel they would make my outfit too period or kitsch.
For one week, I had three or four '50s hats on my watch list on Ebay, and close to right before the first would end I decided they weren't good for me.
Besides being "unusual", hats can be just so much extra work(depending on the type of hat).
Some hats you can just throw on over your head and it will completely cover your hair, but for most I feel like I'd have to do even more with my hair to make it look perfect so that the hat doesn't look out of place, and then sometimes your head starts to itch or get hot....and it can just be a hassle sometimes. Did I mention I'm a guy? Haha.
Who knows though. Maybe I'll get a simple cloche or fedora to wear often.