What suggests to you that these are the same people? Like, if I wore lensless glasses for kicks, would that put me into the "high school bully" class?
You're doing what TFA complains about: making assumptions about people & speaking ill of them because of how they dress. Why make assumptions? Why get mad because some guy wears a V-neck?
It's "cool" to be a nerd now, only in the sense that you can generally like whatever you want and be accepted for it. And I think that's great. Wish it was like that when I was a kid. Hipsters tried to make being a "nerd" "cool" in their usual exclusionary fashion, by ironically appropriating what they thought was ugly and awkward. Unsurprisingly us ugly, awkward folks didn't like that.
EDIT: I have nothing against the guy in the article, to make that clear.
Who the hell knows? Not you. You are just judging them for their style and how well they can pull it off. This tells you nothing of who they actually are.
I'm not sure how old you are & I apologize if this comes off as patronizing, but I promise you'll be happier when you let go of some of this stuff. You're getting pissed off at some guy on a fixie with a "Chthulu is my Homeboy" shirt on because you got bullied in high school for wearing glasses? Two reasons not to do this:
1) It's arbitrary: you don't know if the fixie guy was a bully or bullied as a kid, if it even matters; you're just hating some random person who has nothing to do with your childhood.
2) There is a cost and probably no benefit: being bitter and angry at people is not free of cost- it can make you feel bad, increase your stress, and make other people not want to be around you. What's the cost/benefit ratio on hating PBR drinkers?
Can we stop for a moment to appreciate how amazing this is? As a social development, this is something I could barely even conceptualize when I was in high school at the turn of the millenia.