Most Helpful Guy
Well, I actually prefer girls in winter up here, because it's easier to pick out the ones who have real class from the ones who don't. A nice jacket, jeans, a cute cap and the most important thing would be boots. A pair of good-looking boots clicker-clacketing down the side walks yanks my eyes to the source.
Girls who go to lengths showing off their bodies during winter(skirts or dresses going out on town, any tight leggings at all), are usually very insecure, at least here. If it appears you can't showcase yourself without baring skin or curves, it usually speaks volumes to guys about your confidence. Makes you shark bait on town.
So my tip is, show class and wear boots. That always attracts me. Girl in a miniskirt in summer rarely gets half the attention I give a cute-looking girl who knows to dress herself, in winter. Or summer, for that matter, haha.
Also, wool underwear, as in shirt(exists in t-shirt varieties as well) and leggings, under a sweater and jeans, keeps you warm while not being too bulky like a second sweater would be. Might itch if you're not used to it, but if Michigan is anywhere near as cold as here, guys are very used to girls actually dressing warm instead of freezing half to death in skimpy clothing.
Not that I'm implying that you'd wear a skirt during winter, or anything, just making general observation of college girls here.