Urban Outfitters DV by Dolce Vita Boot, $129 // Michael Kors Runway Watch, $250 // Madewell Leather Rucksack, $248 // Bop Basics Leather Baseball Cap, $88 // Forever 21 Tribal Print Scarf, $9.80 // Forever 21 Gold and Leather Ankle Boots, $42.80 // Dolores Petunia Swarovski Friendship bracelets, $35 ea // ASOS Tailored shorts, $30 // ASOS 15 Denier Tights, $7 // Urban Outfitters Skylar Sunglasses, $16

Back to school fashions vary by region, age, culture, and a whole host of other factors. But if I were able to go back in time and coach my teenage- or twenty-something-year-old self, I would probably take myself shopping for the above items. Once can never have too many pairs of good, basic, black ankle boots (...and please don't call them booties! Pet peeve!). I like the trendier, edgier versions to be on the cheaper side, in case the trend is a flash-in-the-pan. Classic black leather boots without much embellishment should be an investment piece in every woman's wardrobe - they go with everything. Skirt with tights, skinny jeans, even a pair of tailored slacks. Make sure you invest in a comfortable, durable, well-made pair. I love Dolce Vita's iteration above.

I'm also loving the classic collegiate baseball cap, but reworked in a leather style for a bit of an edge that is also kind of timeless looking. Classic "clubmaster" style sunglasses are a must since festival fashion is still going strong, but pick up an affordable pair first before you go splurging on the Ray-Ban version. A classic geometric/tribal print scarf can be tied onto your backpack (I have a soft spot for leather rucksacks) in case your classroom is a bit chilly. And I'm loving the glammed-up take on the classic friendship bracelet - with Swarovski crystals! Totally my thing!