Wow....you have it really rough!!
In Kingston, we had a few massive snowfalls just after Christmas. But when I left town this morning, there was NO snow on the ground whatsoever. It had melted on some warm, rainy days last week. However, this morning it was bitterly cold in Kingston. I got to Toronto (where there is a tiny dusting of snow) and it was still cold, but a whole lot warmer than Kingston.
I think I am in an easier position in other ways, as well. I rarely have to look professional. So if I decide to wear gear because it is what will keep me warm, it's okay. Sometimes I will wear my Gap sweater with my long underwear underneath and that's it.
I hear you on how frustrating it is to try to dress like a real person in this weather. This is where the skinny trousers and boots uniform really helps. My regular long underwear doesn't feel nice under skinnies (too bunchy./ bulky) but silk underwear is okay. Also, I find my Gap Really Skinny pants (not jeans) to be somewhat warmer. So with knee high boots, those pants, wool socks, a cami, a shirt, a merino sweater and a wool jacket PLUS my puffer coat or wool coat, I am all right even on the cold, cold days. That's what I wore today for my travels.