The key to this look is the same as every other hipster look: most of your effort goes into looking like you don't care at all. Meanwhile, since you're getting all educated and whatnot, let's just say that there is a "subtext" to every good hipster outfit that "complicates" its apparent simplicity.
What's the subtext to a good college hipster outfit? Let's have a little tutorial from the teacher's edition, shall we?
Everyone says I'm hot (distressed jeans), but appearance doesn't matter to me (baggy cardigan). I come from money, but I hate pretention and will probably be a social worker for two years before I marry someone from the yacht club (Birkenstocks). I'm well-read and interesting (i.e. I have bangs and named my cat Beckett) and can sometimes correctly use the term "existential" in coffee house conversations...I might not even shave my armpits (literary t-shirt). My parents send me absurd amounts of money (especially when I threaten to join the Peace Corps), but to show solidarity I eat Top Ramen and say "OMG, I am SO broke too!" (Ray Bans).
Plus, this outfit comes with a hipster bonus: You can smirk with superiority when the hopelessly un-hip girl next to you exclaims, "Oh, I looove Maya Angel-owe!" Rookie!