I tried to wear a Trilby but it made my head look weirder than normal.
Normally people don't notice how big my head is until they try putting hats on me and the shorter brim of a Trilby just makes me look like the Mekon, in a hat.
The bigger the brim the smaller my head looks (in a Fez I look like an escapee from Easter Island).
Though when I wear a Fedora I tend to get a lot of this (I have a rather hasidic look and demeanor generally so add the hat and ...) :
