I don’t like those small brimmed ones, I think they are called a Trilby. If Federline would wear it, I wouldn’t.
I wear a wide brimmed one, more like something The Shadow would wear, but I usually only wear it when I dress nice and it works with a suit and trench coat. And I usually only wear it when it’s cold out, as its a fairly warm wool one. When I wear it more casually it’s with this really thick, vintage dead stock brown wool coat. I think I pull it off well.
