I feel your pain. I used to be a stylish hat wearer. I could wear anything. I don't know what has happened to my head as I've got older, but now hats look awful on me.
In winter I seem to look like a burglar whatever hat I wear, and in summer I look like a startled owl in all hats. S'not fair. :(
The closest I can get to not looking laughable is something like this hat