Due to Berlin’s reputation for being a party city, everyone goes there to, well, party. At the same time, Berlin is filled with Hipsters who pride themselves on appearing as though they got dressed in the dark in a thrift shop that hasn’t accepted any donations since 1985
Being a Hipster has become a pretentious phenomenon in and of itself before the Hipsters started controlling the clubs in Berlin. Originally intended as a counter-pop-culture-movement, it has since become the mainstream "cool club" to belong to. You have to take time to look like you didn't take time. You have to work hard to look disinterested. And you can only be into things while they're still outside of mainstream culture. The whole concept of "not caring" has been turned on its head, since now you have to care a lot to look like you don't care. (Generally speaking, of course. There are some people where being a hipster just comes naturally.) There was an awesome episode of Happy Endings about this last season, as well as this too-long-but-still-hilarious sketch from the Harvard Sailing Club.
Anyway, the Hipsters often control entry to the bars and clubs and take unbelievable pleasure in turning people away for whatever inane reason they come up with that evening. As a result, people often "go Hipster" in order to get into particular clubs. In other words, the Hipsters themselves have taken their counter-mainstream cultures and forced it to become mainstream in Berlin. Anyone who wants to get into a club assumes a Hipster persona, and the longer they stay in Berlin, the more Hipster they become for real.
I was turned away from some random bar for showing up in a group (they let people in one by one, but turned away anyone who was in a group of more than two) and turned away from Watergate because one of our people was too fancy (he was wearing a plain white button-up shirt instead of a t-shirt with some ironic graphic image on it). Berghain, the most famous club still in existence in Berlin, has a reputation for making people wait in line for up to two hours, only to reject them for no reason once they get to the door. (I’ve also been informed that Cookies also has the Hipster Pretention Phenomenon from time to time, but I think we got there early enough to avoid that issue.) Visiting Berghain, Watergate, or Cookies is worth it at least once just to see whether or not you can pull off Hipster Chic. Luckily, because it’s Berlin, every time you’re turned away, there are three more clubs right next door waiting for you to arrive.
As a result, whenever I go to these places, I just arbitrarily put on a random conglomeration of clothes without looking in the mirror. I know that the mismatching nature of my outfit, which would normally drive me crazy, will be exactly what I need to get past the doorman. I've even purchased a pair of ankle boots that I ironically wear in warm weather with a summer dress and mismatching scarf. If I want to go super Hipster? I put on my square, thick-rimmed glasses - something I ordinarily don't need outside of the classroom.
Despite the inherent irony and pretention that exists in Berlin Hipster culture, I love the influence it has had on the city - there's always some crazy art exhibit or underground club, people wear clothes that are interesting to look at, and no one gets stressed about life. Berlin lives in the now and the only question you have to worry about is, "How long is now?"