We know it's hard to let go of that Summer break freedom, but let's face the facts: we can hear those (figurative) school bells beckoning the return of class, study sessions, and dorm life. Before you're knee-deep in textbook shopping, we've made the process of back-to-school shopping an easy and superstylish one. Instead of going overboard on one-off pieces, focus on investing in staples that can not only play part in a chic transitional wardrobe, but nail the whole schoolgirl-meets-sophisticated-lady vibe, too. We've found the perfect dark-wash cigarette jeans that will get you through late-night library brainstorms and look great on your first date with the boy across the hall. There's also the footwear must haves: a classic ankle boot, a statement metallic sandal, and an Audrey Hepburn-inspired skimmer flat in the sweetest nude hue. Lest we forget, we've culled a versatile mix of slinky sheaths, polished layers, and eye-catching accents, too. It's time to put those erudite skills to the test; first up, commit this equation to memory — 16 styling essentials, 17 ways to wear them, with an infinite number of future outfit combo possibilities to ace the Fall semester.