What to Wear: Rainy Day

1. Alexander Wang Sweatshirt, Mr. Porter. Investing in a basic sweatshirt will carry you through the Fall- especially those overly chilly classrooms. This is perfect for an overcast day as it can handle a little rain on its own, or be worn under a rain jacket.

2. Denim Skirt, Topshop. This dark denim skirt is another update to your summer cutoffs (and again- you can totally wear it to class). I know it seems like the last time you bought a denim skirt you were in the dressing room at Abercrombie and Fitch getting ready for a middle school dance, but trust me, the new styles are less ripped and more flattering.

3. Hunter Boots, Hunter.com. Hunter boots are such a staple for me that I keep a pair in my car. It may seem annoying to wear them during the Summer, but there won't be a puddle you can't handle.

4. Marc by Marc Jacobs Tote, Shopbop. While this tote looks like it is made of leather, it is actually neoprene (read:pretty waterproof). It won't get worn in bad weather, and the structure will hold up over time. It's also able to fit a laptop and notebooks for class.