I have had a pair of Hi-Tecs that I have use in the Winter for years.  I mostly use them for when I am clearing the driveway with our snowthrower.  They are very comfortable and waterproof.

I bought my son a pair of these when he became a Boy Scout. One of the first things he did was a five mile hike in these and they didn't bother him at all!  I thought he should break them in but he said they were fine.

So, waterproof, comfortable, and extremely inexpensive.  You can't go wrong!