Note: This one has been edited.
I never thought about the whole Hipster thing much while it was happening (is it over now?) but looking back I wonder if there wasn't some element in the media coverage of it that was far less about Hipsters themselves than something else. And media coverage was how I experienced the subculture.
I never found Hipsters annoying. The term was used as an insult by people I knew - implying a kind of deeply flawed desperation to be cool. Flawed in that being a hipster was precisely uncool. And it implied a longing to fit in, to conform. But no one used any other sub-culture in the same way or to the same extent. When I was Hipster aged - my sense was the sub-culture was largely composed of white people aged 18-30 - Slackers were the Hipster equivalent. The difference, aside from cataloguing the attributes of the two types, was being a Slacker implied a social and political position - Slackers were Slackers because there was no point in trying. The game was rigged. Slackers were non-political because there was no way for them to be political. They didn't want the successful career because success was determined by factors beyond their control - a fact that is still largely true but more widely ignored. Hipsterism never implied much to me except a preference for tight jeans and facial hair (for guys) or straw hats (for ladies). The skinny jeans weren't attractive (at least to me) but since many of those making fun of Hipsters had once worn bell bottoms, or stone washed jeans with strategically torn knees, I question their right to make aesthetic judgements. I also question why they cared.
In retrospect, there seems a weird antagonism not just to hipsters but to the youth culture of the time (of which hipsterism was nothing more than the prevalent mode). My experience of the culture was mostly through the media. The young people I knew during that era (say 2005 to 2010) were architecture students. And no matter what is happening in either the dominant or sub-cultures, architecture students have their own thing. They care about details - well designed shoes, carefully chosen watches and pens, little things like jewelry and accessories. For the most part they lean towards monochrome - a trend that probably began with the original hipsters in the 50s and has been preserved in that highly artificial environment. There have been a lot of discussions (within the architecture community) about why architects wear black. The most absurd position I ever heard was that they were representing themselves as the "vanishing point" in a perspective drawing. I vacillate between thinking they (we) want to look kind of formal without sacrificing our prerogative as "creatives" to forego the suit and tie and thinking it is because we don't want the world to know we can't match colours. Anyway...
The media didn't just disdain Hipsters or Hipsterism, they were kind of hateful about it. It isn't unusual for someone like John Stewart to be mean or angry for comic effect (or more sincerely as in the case of the 9-11 First Responders) but for him (or the Daily Show correspondents) to be excessively mean to any aspect of youth culture is strange. I can't think of any other sub-culture (particularly youth sub-culture) that was derided in the same way.
I think anger against an almost entirely harmless sub-culture was about something fundamentally else. Something that had very little to do with the sub-culture itself - with the possible exception of its membership. Why else would people get seriously bothered by other people taking pictures of food? Or wearing straw hats? Or moustaches? There was nothing offensive about them. They weren't dangerous, or political, or adversarial towards anyone. I have difficulty thinking of a less offensive sub-culture. Serious sport fans are far more annoying to me than people excessively proud of their facial hair.
"The joke is over when even victory is a downhill run into hardship, disappointment, and a queasy sense of betrayal. If you can laugh in the face of these things, you are probably ready for a staff job with a serious presidential candidate" - Hunter Thompson, Better Than Sex: Confessions of a Political Junkie
After the September 11, 2001 terrorist attacks the media acted like the whole world had changed. It hadn't. Almost nothing had changed (unless you believe some element of the US government destroyed the Twin Towers, a theory I'm neither willing to accept or reject). But the US went crazy. And, as a result, people started thinking politics really mattered again. Then the Bush White House got the Patriot Act enacted and started invading people. That made politics seem to matter even more. It is my belief people on both sides were offended by a group of relatively affluent, relatively educated group of people who chose to be more interested in Instagram than Congressional races. Who valued Pabst Blue Ribbon more than the Freedom of Information Act. Who didn't Occupy anything except antique stores and coffee shops.
Skinny jeans aside, I think the Hipsters were fundamentally right in their political stance. I like watching politics. It's a blood sport with no winners. Since no one is worth cheering for that doesn't matter much. I think Hunter Thompson captured the mood in America in 1992 perfectly. The only thing that mattered was defeating George Bush the Greater. When his son successfully stole the 2000 election that was the final straw. Global terrorism or no, run-away economy set to self-destruct or no, immanent environmental catastrophe or no, one thing you can control is the filter on the picture you just took with your iPhone (probably of a meal you are about to eat).
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