Gregg Gorse asks this question (or at least, he did in 2014, but it’s new to me in 2015):
Why does being Hipster often have negative connotations? I feel like, to some, being Hipster can mean being a breaker of cultural norms. Breaking these norms comes through pursuing difference. In that way, you could say a Hipster is an individual who seeks out cultural variance. Someone who goes against the grain. Doesn’t jump on the bandwagon. Surfs on a lonely tidal wave. You get the picture. If Hipster can be viewed as a label for somebody who strives to be different, then Hipsters must be pretty unique. Being unique isn’t that bad of a thing.
Simple: Because hipsters are not unique. They have a label, a look, an attitude and enough checklist fodder to fill entire books across multiple literary genres. In other words, the exact opposite of surfing a lonely tidal wave.
This is not an indictment of hipsters; in fact, I share many hipster tendencies. As a child, I wore thick glasses, sipped my grandfather’s cheap beer, wore skinny jeans and rode a single-speed bicycle. As a teenager, I eschewed Nirvana CDs in favor of vinyl records from the 1980s. All through that era, I lived in what is now a gentrified neighborhood, while wearing a lot of secondhand clothes adorned with retro logos and concerts I never attended. Today I have a retro-styled record player and own an iPhone and a Mac laptop that I often take to coffeehouses. I care for the environment and sometimes shop at Whole Foods. I was deep into most of this long before it was cool to say, “before it was cool.”
But no one would ever mistake me for a hipster. Hipster style makes me look square, even if in many cases its adherents make (or otherwise just have) more money than I do. (Most hipsters deny their hipsterdom, so again, cred.)
I love my hipster friends, assuming I have any left now. But let’s not pretend being a hipster is some brave or noble stance, any more than my clean-shaven face is a brave and noble rebellion against beards. Hipsterdom does not make people unique. Other things might. But not that.
A truly grain-going-againster doesn’t have a term, because they are busy being themselves, and thus aren’t morphing themselves into clones of their friends. They’re hard to pin down. And I, at least, find that super-interesting.
Fifteen years ago, hipsters were much less common. Does that mean people weren’t seeking outsidership in 2000? Of course not. It just took a different form then, maybe in nu-metal/rap-rock (or whatever other lamestream trend was hot at the time; I didn’t pay attention). It’s mainly an aesthetic difference. But someone who was truly their own person then is probably the same person now.
The one thing that is justified to dislike about hipsters is that some are exclusionary, which is against the outcast code (to the extent that there is one). Some hipsters (though not most) can be every bit as snooty, snobbish and elitist as the country-club crowd in a 1980s class-warfare comedy. How appropriately ironic.
You wouldn’t understand.