Grunge did not die for this

So what is a hipster?
According to my buddy, Ren, who seems to know more about it than I do ("Because I hate hipsters." - My buddy, Ren) they are middle class kids who want to be different and cool like the grunge kids of the 90s, so they wear a lot of plaid.  And grow beards.  And play acoustic instruments.  Or something.  Except that at this point in the year of our Lord, 2015, hipster as a subculture has become so popular that it is no longer hip to be hipster.
Also according to my buddy, Ren, even though he is not a hipster, because he has interest in things that are not popular to mainstream audiences, he is probably more hipster than self-proclaimed hipsters are.  And then he went on a bit of a tirade about how hipsters say they like Twin Peaks but they do not really understand it.  (Which is a viable complaint when you are as passionate about Twin Peaks as my buddy, Ren.)
So I am going to classify hipsters in the style of my buddy, Ren.  Hipsters are people who want to be ahead of the curve, so they wear plaid and play acoustics and grow beards and wear fake glasses.  The dictionary definition is:
a person who follows the latest trends and fashions, especially those regarded as being outside the cultural mainstream.
-which is both less specific and less disdainful.  But it does still fit.

Now, I have difficulty with really explaining this with things that exemplify what hipsters really are.  And a large part of that comes from my confusion with the differences between hipster, alternative, and indie subcultures.  Scott Pilgrim vs. The World was one of the first works that came to mind, but although some of the characters featured in the universe of Scott Pilgrim might be hipsters, the story is largely one of the indie music scene.  And the film and comic series Scott Pilgrim itself has certainly gained enough popularity that it would be considered too mainstream to be hipster.

Hipster characters in a non-hipster work

Or maybe a show like Portlandia works, which is still probably too mainstream to be hipster, but nonetheless features many characters that would probably fall into the subculture.  With the coffee shops, underground music, and eccentric 20-somethings galore, the show itself sort of presents us with a bizarre, sometimes abstract world, that seems to be filled with people who might be considered hipsters.
Even though it might not be a hipster work in of itself, it is a show that regularly parodies hipsters.
In fact, here is a link to 15 Spot-on Hipster Parodies from Portlandia, which shows this quite well.

Battle of the Gentle Bands!

I am just grasping at straws, here.

According to this list of The Most Hipster Musicians and Groups, Neutral Milk Hotel is the most hipster band.  I know some NMH fans who would be offended by this assertion.  Nevertheless, Neutral Milk Hotel live at the Ottowa Folk Festival seems pretty damn hipster to me.
One of my favorite bands, Fleet Foxes, is #5, so here is one of their music videos (one of my favorite music videos) for good measure.

So hipster music, in contemporary terms, seems to have moved on from jazz to more folk-like songs to accentuate the sort of natural quality of hipster style.

Hipster in contemporary terms is such a broad style that it more than anything seems to be general mainstream youth style than an anti-mainstream subculture.  They have good music.  They have good coffee.  I can dig it.