I go to UMN-TC, but UW is a kinda similar school.
Usually, snow is not a huge concern because most colleges up here have excellent ground crews that get out in the mornings way early and clear any overnight snow. I know at UMN I can survive winter in my regular shoes. Only times you have to worry about snow is when it's snowing during the day. Just pick up a pair of waterproof hiking boots, you don't need to go nuts and get sorel boots or anything.
The women - well, I'd completely disagree on this point. I'm making a total stereotype here, but I'd bet that the women who go to public florida schools probably are probably a little more on the....side. UW-madison is going to have PLENTY of good looking women. Sure during the winter they wear more clothing, but it leaves something to the imagination!. Plus there's always the opportunity to meet a nice, well-mannered midwestern girl
In terms of winter clothing, don't buy anything until you get up there. Selection will be much better.... At most stores up in these parts you can completely deck yourself out with some great gear for a good price. You can also deck yourself out with some REALLY GREAT gear at an expensive price...
Also, layering IS key. Buy some thermal underwears.
And, unfortunately, you can't predict how snow will be - in recent years, we've almost had snowless xmas. But then we've also had 3-foot snowfalls in october-november. If you're relying on public transit, you'll be fine.... people know how to get around in the snow.