Improperly wearing one shows a lack of self-awareness. It has a (formerly) classy reputation because it's meant to be worn with a suit. For one reason or another, it fell out of vogue with the suit-wearing crowd, and was picked up by hipsters looking to add something to their ensemble. You see, even then, we're talking about hipsters who've spent time and money coming up with a look that (in theory) is supposed to echo and play with that older style. It may not match, per se, but it's part of a concerted effort to look good.

Now we turn to the modern neck beard: he wears the fedora in order to get some of that, "class," we talked about. Thing is, it was never that the fedora made anybody look classy, it was that well-dressed people just happened to wear them at one time or another. If you wear cargo shorts and a Naruto graphic button-up, a fedora isn't going to save that outfit. It just makes the wearer look like a dope. The only guys that do this are the ones who genuinely do not understand how to dress themselves, and that, as I said, shows a lack of self-awareness.