Your seasonal staple fitted. It doesn't hurt to have one favorite fitted hat each season. And for the guys who don't wear fitted hats– you may not have any in your closet now, but there will probably be atleast one weekend, or rainy afternoon, where you wish you had a nice fitted to just switch it up a little bit. Check out Fitted Hats.
Cardigans. One can never have too many cardigans, so it's okay to slightly stock up. They take you from Fall to Spring without a hitch, while making cameos during the Summer season.
T.U.G Idea: When buying a "varsity" type sweater, get one that doesn't boldly sport the designer's logo so that you can customize and authenticate it. Go to your campus bookstore and purchase a custom embroidered patch of your university's emblem. Then iron and sew it onto the sweater. Some of you are probably like, "what, sew!", lol. Well, if you don't want to sew it yourself then most dry cleaners (with tailoring services) will sew in on for a few bucks.