The Look – The basic idea behind dressing like a hipster is not trying whatsoever. In fact, getting dressed in the dark would probably be an excellent way to nail the carefree, relaxed look that hipsters embody. Therefore, my main advice to you for dressing like a hipster: don’t care.
The Components -If you’re anything like me, not caring about how your outfit is not an option. Therefore, I’ve compiled a list of a few key wardrobe necessities that will no doubt let people know “I AM A HIPSTER” right away.
The Glasses: A hipster always wears frames that are too thick to not have been inspired by Dexter’s Laboratory
The Flannel: I shouldn’t even have to tell you this but it should be oversized and never match the rest of your outfit.
The Hat: Any respectable hipster should own at least two beanies, one must be gray. Fedoras are also accepted (especially those with tiny feathers).
The Scarf: Buy lots! Buy them in every shape, size, pattern or color. You’ll be warm and stylish, it’s a win-win.
The Cardigan: Cardigans are a staple of the hipster wardrobe. They can be found anywhere from the Gap to thrift stores. Hipsters generally sport cardigans that are too large with a deep v-neck and buttons (which looks awesome over your v-neck tee).

The Shoes: Hipsters like to walk, a lot, so the shoes should be comfortable. Try checking out a pair of oxfords, but your dirty old Converse will also fit the bill.
The Ironic Sweatshirt: This sweatshirt should be a pull-over. The front should have either kittens on it, Christmas décor or both. Also, it should be worn un-ironically. Or ironically. Whatever.

The Real Deal
While people (myself included) may joke about hipster fashion, there is something to be said for the true hipsters. These people are unabashedly themselves and never let anyone tell them who to be, what to do and especially not how to dress. So, if you know a hipster or if you are a hipster (not that you’d know it, but maybe you suspect) then more power to you, and check out this contest over at College Magazine. Happy hipster-ing!
P.S. Don’t forget your skinny jeans.