There's just something about a gray sweatshirt. I've long been a fan of pairing one with a super fancy and heavily embellished (or even metallic) skirt or a pair of sleek black ankle-length pants and sky-high heels—it somehow brings the OTT and seriousness of whatever else you are wearing back down to earth. If dressing is a bit of a balancing act, the gray sweatshirt is the casual counterpart. And it's only the gray version. White sweatshirts look schlubby; black, too much like you are trying to pull a fast one and wear a sweatshirt where a fancier top should be. Gray really is the ideal color. Jane from Sea of Shoes above, agrees—she pairs hers with some serious Marni booties. Check out a few of the best ($$$$ and not so pricey) options out there...