I just want to get a few things out of the way first. It is likely that everything you know about hipsters is bad information, as the definition has been warped. Here's the initial definition that all of the hate spawned from:
Hipster: Someone who picks certain aspects of cultures or subcultures that they like, instead of embracing the entire culture or subculture.
Then we have false definitions like this one, made due to the misguided nature of hipsters as a meme:
Hipster: Someone who only likes things from when before they were born.
and this:
Hipster: Someone who only likes things that aren't mainstream.
Those aren't true.
One would want to be a hipster, because you don't have to have things you dislike about subcultures/fandoms with the things you do, and you can pick other things, too. Want to be a guy who wears lumberjack clothes, but plays baseball? Go do that! Want to use typewriters, but play Xbox 360 games? Right this way! Moving into fandoms, Want to be a brony who hates background ponies and instead prefers background elements in video games? Do it!
There are better examples, but that deviates from what my points are.
My points are:
1. Hipsters are regular people, and need to be treated that way
2. That person in the pink hoodie who thinks he's a hipster is probably NOT a hipster.
3. It's easy to understand why one would want to be a hipster.