I'd like to point out that most of these people are wearing trilbies, not fedoras. A fedora has a much wider brim and looks like a cross between the trilby and a cowboy hat. But I'll just use "fedora" to mean trilby here because that's how it's commonly used.
Now, the headwear itself isn't the problem. Worn properly, the fedora can be a great piece of head wear and I'm quite annoyed at how horribly it's been abused by the neckbeards. Most of them are not wearing it properly. It's a piece of formal wear that is meant to be part of formal attire, as in some kind of suit or a nice jacket and slacks. It is not meant to be worn with shorts and a graphic t-shirt or casually in general.
Fedora worn properly:
Fedora worn improperly:
It's mismatched, like wearing a smoking jacket with athletic shorts. The fedora, worn improperly, makes it look you can't dress yourself. They're trying to use the fedora to add style and class to their outfits, but the problem is that shorts and a t-shirt is not a classy or stylish outfit, and the result is that the person comes off as awkward and appears to have no sense of style or of their appearance, which pretty much fits the "neckbeard" stereotype dead-on.
RatherDull said:
It's more about what attracts a person to a Fedora.
Fedoras are, more often not, worn by someone who doesn't have a clear sense of fashion identity and it really just consists of whatever they think makes them look cool. Which stems from a lack of confidence. That lack of confidence often leads to the "nice guy."
The truth of the matter is that with any piece of apparel that looks cool, it is because the person makes it look cool. Not the other way around.
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Also this. Having a personal style requires a lot of confidence. But it's the confidence in the identity that creates the style which informs the appearance, the neckbeards have this backwards and the result is quite obvious. They try to wear a certain style that to them symbolizes refinement and class, but make no effort to actually be refined and classy, so they aren't actually refined and classy, and thus no amount of nice apparel will create an air of refinement and class.
So what does it say about a person, when that person tries to ape a style they don't actually possess and have no interest in actually building? Its says that the person doesn't have much confidence in who he is, and even more so, it makes him look shallow because it signifies that he thinks style and identity are only matters of appearance. Shallow and lacking confidence...hmmm...just like "nice guys" (TM). And also just unattractive traits in general.
But it's not the hat that's bad. If you genuinely think that a fedora makes you look better, then absolutely go for it, no judgment. If you think it makes you look better and if you can look at yourself in the mirror wearing said hat and you think "This makes me feel better about myself and is how I want people to see me" then great. Wear whatever you want, if that's the case. Matt Smith manages to look damn sexy wearing a fez and a bowtie for crap's sake, both of which would normally be really...ill-advised to wear out in public in normal cases. But if you're just doing it because you think it will give you an element of character that you don't have, you're just making an ass of yourself.