Love hats. They must have wide brims to fit my big features and wide shoulders: if I take a hat with a mid-size brim and put it on my head, the brim magically shrinks to an inch wide. So, fedoras and floppy hats, mostly. I can get away with a beret sometimes, if it is big and floppy and I can tuck in all my back hair, otherwise no.
My hat style has been compromised by glasses and greying hair, which narrow the options/change what used to work; and by fewer opportunities to wear one, between singing in the church choir (I was always known for having a hat on in church, sadly no more) and by the darn sunroof in my car which makes the ceiling too low to drive comfortably wearing one.
I often shop the mens dept to get hats to fit my big head. DD on the other hand at age 28 found a perfect fit in the toddler dept!