Hey CD....If you have a good pair of waterproof walking boots, you could use them instead of a big heavy pair of winter boots, and then wear gaiters over them if you go walking in the snow...That's what is best for hicking, and you can wear your boots without the gaiters when in town.
And steel toe...well that can get really cold because it's metal and metal gets cold outside, so you might freeze your toes! Hhaha!
As long as you wear good thermal socks and your feet don't get wet, you will be ok. When I work in the forest, I always wear 'bamas' in my boots, they keep your feet warm and dry...And I mean really dry! At the end of the day, I could squeeze water out of them but the inside was still dry...And they prevent blisters.
Thermal underwear is small and light and will also keep you warm even if you get wet...Plus you can use them as pyjama's since they are so comfortable, and the top can also be worn alone and still look good. I stongly recommend polypropylen fabric, forget about cotton and all natural fabrics coz they get wet and you'll freeze.
I would only bring your big parka, and maybe a warm fleece, nothing more. Since you'll be wearing your parka all the time, you should not worry about it being big.