Fedoras work for Jon Hamm because he has the chiseled facial aesthetics to pull it off. Some double chinned pink faced schlub wearing one (ie, 95%+ of fedora owners) looks stupid.
And yes, most women past college age have something long term, married, etc. Most people do. I guess if you want to be single still, you can skew younger (college girls) or older (divorcees). That or pull a GAF and go without. Just understand you're in a dwindling minority and if you're cool with that, that's fine. Just understand that it isn't going to be the college days.