With the reddit and others blazing with hate towards fedoras, I'm all for fedoras.
That said, if you don't want to look dork, you'll have to think about the overall clothes you're wearing with the fedora. Fedora with a fitting suit and a crombie coat is just superb. Fedora with casual clothes can work, but takes some effort. Fedora with a t-shirt, it'll never work, unless the hat happens to be a prop and you're a rap star on a stage.
Also, fedora with glasses... one needs to be even more careful and stick to the classics. No amount of chutzpah will make Oakleys work with a fedora.
That said, if you don't want to look dork, you'll have to think about the overall clothes you're wearing with the fedora. Fedora with a fitting suit and a crombie coat is just superb. Fedora with casual clothes can work, but takes some effort. Fedora with a t-shirt, it'll never work, unless the hat happens to be a prop and you're a rap star on a stage.
Also, fedora with glasses... one needs to be even more careful and stick to the classics. No amount of chutzpah will make Oakleys work with a fedora.