Hipster/Beatnik Analysis

Hipsters are not about irony.  They are about hypocrisy.
Brag about vinyl record collection... doesn't own a vinyl record player, keeps all music on MacBook.  Yammer about how antique stuff is superior to modern contrivances... have nervous breakdown if they keep the same iPhone for three months straight.  Eat kale, ride bikes, talk nonstop about how gluten is bad for you... spend the weekend snorting cocaine in bathrooms.  Blog about WalMart is driving away all the local, hard-working business owners... while slurping on coffee from Starbucks.  Buy antique, retro-looking t-shirts with pre-faded logos from a bygone, pre-internet era... from an online catalog.
Hipsters are the distilled essence of all the phoniness of every counter-culture that has preceded them.  They have inverted emptiness and made it into their homes.  They are offensive to the degree in which one values honesty.

What's bad about hipsters is that they're hypocritical. In their quest to get away from the mainstream, they have created a subculture that has become part of the mainstream. That is because they openly flaunt the aspects of their subculture and talk of why they think their way of life is the best, which attract disillusioned people who think that they are getting away from the vox populi, when in reality they are simply joining another part of it that pretends it is not. It is sort of like a teenager that states to everyone they know that nobody can tell them what to do them one day, and then the next day they go to school and sit down in a desk and accept what a teacher tells them to do. It defeats the purpose of publicly stating that no one can tell them what to do. It's hypocritical.
Most of them used to be emo/scene kids back in the 90's/early 00's and the paradox of uniform individuality seems to be common thread through most social fads. They're just a manifestation of postmodernism  really, which isn't in and of itself a bad thing-but what is-is following trends out of fear of social rejection or ridicule even if that trend is ridiculed by others outside of it, older or who don't understand it. A lot of people spend an awful lot of time and energy pretending to be someone else and hipsters are no different, it's a silent tragedy.

What's so bad about hipsters? Gentrification. Something not even alluded to here. Perhaps it's outside of your experience. 
Adhering to such a strict look or lifestyle makes this basically meaningless and soulless youth movement easily identifiable to property developers and advertisers as a monied demographic without conscious or code. The rapid destruction and displacement of communities in cities, not just in America, have been shown to directly follow in the wake of ironic glasses and whimsical street art. 
People's homes and social spaces are being systematically taken away from them to cater directly to this demographic. The 'hipster' look and lifestyle is a symbol of economic power.

The problem with SOME hipsters is that they appropriate different elements of cultures and then become cultural critics of the culture they have appropriated. Because this hypothetical hipster "found' some esoteric style before you, or he has more knowledge about it than you, he suddenly has the right to 1) say you're not cool (whatever that means) or 2) you shouldn't appropriate that because you don't really know about it, 'understand it' or adopted it to late. 
Ultimately, they are social engineers who inflate their own status, in our informal social hierarchy, through cultural elitism. It's annoying as fuck and pretty much a more nuanced form of "High School'. 
Iconoclasm is not authentic when the goal is to be iconoclastic

Hipster culture now feel more Dadaist than it does convenient and/or conservative. Just for sake, or just in spite but it is definitely a bandwagoned movement; it looks cool, defying, and appeals to everyone in their late teens- 20 somethings. Hipsters adorn the following ten stereotypes:

- A nice Macbook... w/ f'n stickers and decals slapped on the side of it (strong sign)
- Fixed Gear Bicycles ( definitely a strong sign)
- Big ass glasses
- A hat, any hat, doesn't matter, grab a beanie and join the club. Fedoras are more of a mascot.
- SKINNY TAPERED JEANS...worn by guys. Just...how can you breathe down there? (Instant hipster)
- Smokes cigarettes and drinks Starbucks coffee (bad combination, strong sign)
- Politically correct for the most part, will associate themselves as libertarians or anarchists
- Have student loan debt & majored in something they didn't even work hard in
- Has a strong reference to everything 90s, nostalgia gaggers for the most part
- Strong sense of narcissism

The problem with hipsters is not so much what they listen to, or what they wear... It's more about how they act about it. Hipsters are people who show off about what band they listen to, because they think it makes them seem cultured. Same goes with clothes, movies, etc. It's basically snobbery- they're just trying to seem cool, to seem clever.
Hipsters are gross because they are pretentious, vacant, and pursue image rather than substance.  They strive for mediocrity rather than greatness, collectivism over greatness, intuition over rationality.  Their views are self-contradictory and hypocritical.
On the positive side, their strident quest for rebelliousness of image has necessarily instilled a refusal to accept self-consciousness or the judgments of others.  And that can make them fun to be around, as long as they can't identify anything in you that smacks of something vaguely reminiscent of The Enemy.  The Enemy is in no way clear, understood, or defined, but rather a mystical sentiment associated with words like 'corporate, conservative, science, money, practical, define, rational, logical, precise, purpose, meaning,' and many, many others.
Anyone who is truly revolutionary, they will not accept or include, because he will not bother with the mustache, the top hat, or any of the other images of group affiliation with a group that is solely affiliated around image.  And because, frankly, he will actually be different, whereas hipsters aside from their fashion choices, are supremely normal and worshipers of normalcy.
 They very carefully play within all the rules of the status quo, even in their speech and thoughts.   

They are the new zombie class of a society that explicitly encourages nominal and superficial "uniqueness," as a spice for the blandness of conformist behavior.
   They are the cowards who admired the boldness of rebels, sought to emulate them as weaklings do, but without any understanding of what make the rebel a rebel in the first place.