
First read this article in Adbusters entitled "Hipster: The Dead End of Civilization." I think it adequately sums up why hipsters are a bad thing and indirectly explains the difference between a true hipster and somebody who merely subscribes to modern fashions and wears tight pants. To summarize, it comes down to hipsters standing for nothing really except seeking authenticity through consumerism. Co-opting working class values and trends and spending lots of money doing it.
A lot of quote-unquote hipsters are really just artsy people who do cool things like sell street food in The Mission or make swimming pools out of dumpsters in Brooklyn. These people are not actually hipsters in my eyes. They are doing something and creating interesting things rather than buying something obscure and then ditching it when it isn't obscure or authentic enough for them anymore.
Again, great article, but I disagree with it where it draws a bright line between hipsters and punks...which brings me to the penultimate punk band, The Sex Pistols.
They declared their allegiance to the working classes and held mainstream society in contempt but really I think it's pretty safe to say they were just intellectually retarded nihilists consumed with image, self-indulgence and popularity. Sound familiar?
Sid Vicious was chosen for his attitude rather than his musical ability and they ended up becoming just as vacuous and rich as the ruling classes and cliched rockers they claimed to abhor.

Punk was sort of an interesting counter-culture moment and I see the value in bands like The Ramones and The Clash. I like the do-it-yourself attitude and the quesitoning of authority, but check out this quote from Johnny Rotten: "[The Ramones] were all long-haired and of no interest to me. I didn't like their image, what they stood for, or anything about them; They were hilarious but you can only go so far with 'duh-dur-dur-duh'. I've heard it. Next. Move on."
Newsflash...The Ramones were developing your sound while you were busy tearing holes in your Pink Floyd shirts and spending money on hair gel and red dye. Get over yourselves. Who cares how long their hair was?
Also, The Pistols (and pretty much all punks and hipsters) constantly talked about how much they hated hippies. The punk-hippie dichotomy really deserves to be explored fully in another post, but when you come down to it, they really weren't that different. The main difference I see is that at least hippies were trying to do something and change the world* while punks were consumed more with rebelling for the sake of rebelling and were ultimately a much more selfish group of blowhards. It's the same difference between a hiptser and somebody who isn't utterly worthless.
*That they failed and ended up becoming the big wigs they were rebelling against is irrelevant to me. At least they initially stood for something.