Never have I been more excited to show off my preppy side – which, I should say, is fairly nonexistent anyway. But if the Marc by Marc Jacobs Top Schooly Printed Leather Shoulder Bag gives me a chance to express a different sense of style, I’m all for it. I love this boxy bag, from its deep blue plaid to its pretty burgundy canvas lining. Plaid patterns are always in style, so I can count on wearing it every year without fail. Available for $400 at Net-a-Porter.