I believe everyone here who says they've never heard of the connotations and think fedoras are cool because of the way they look, but the fact that the friendzone/nice guy/forever alone thing paired with fedoras is so widespread there are several websites and blogs dedicated to mocking fedoras and the people who wear them, make the connotations real. You can wear a fedora all you want, and personally you know you're not one of those Nice Guys (none of the people on this forum seems to be like that at all), but if someone has a negative reaction to your head wear of choice at least you know why.
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I give people the benefit of the doubt more often than not, but it's impossible to be completely neutral regarding anything. To me, fedoras really do represent those things I posted. Plus, purely stylistically speaking, the ball cap + formal wear/fedora + t-shirt thing Jace said is pretty good. I kind of like to keep casual and formal clothes separate.