Get some wool socks to wear in the hiking boots & Uggs. If the uggs are real wool lined they should be fine. Many people wear tennis shoes all winter for errands, only wearing boots when spending time outside. You can always hit up a second hand store for things you find a need for. Leggins to layer under jeans would be good too. Of course a good coat, gloves, hats, and a scarf. Wool is super warm & water resistant. Hope that helps!