For those of you who have to think about life post-Summer lazin', aka slowly but surely reset to back-to-school mode, why not go the prepster route? Sure it can look a little over the top, but nothing says studious and intelligent like a good plaid accent, dainty headband, and cardigan set. Gossip Girl's Blair Waldorf nails the look, right down to the heeled oxfords and textured tights. Now it may be too hot to contemplate sweater sets but you have to start somewhere, right? Head to one of these five prepped out New York spots and stock up accordingly. Add some librarian glasses to the mix, pick up some existential lit from The Strand, and put that light reading to good use in Washington Square Park — even the Queen Bee would be proud of you.