Just in case anyone else is still reading this for cold climate advice, I thought I'd add my two cents even though I'm late to the party.
For years I made the mistake of ignoring my legs when trying to dress warmly. I'd have a billion layers on my top half, a hat, gloves, and then just... jeans. It's true that it's the wind, not just the cold, that really makes you feel cold. I've never been skiing (saw too many injuries among friends when I was a teenager), but I have two pairs of ski pants that I wear when outside with the dog, etc. They're a bit... swishy... for everyday wear, but they're great for around the yard, hiking, etc. I wear long underwear or thicker tight-fitting pants underneath, both to add warmth and to decrease the need for frequent washing.
If you're not in a situation where you can wear ski pants, then at least wear a coat that covers your butt and upper thighs. I've found that helps a lot. I see all these trendy cropped down puffy coats lately, and I wonder where on earth they expect people to wear them!
Seems like everyone has their preferred boot. I love my Bogs. They're waterproof and temperature rated to -58F/-50C. Even the ones with laces are easy to slip on/off for quick trips to the yard. And they're actually comfortable -- not overly tight or stiff. Micro-spikes have saved me from ice more times than I care to remember, and they keep me from hibernating inside due to fear of slipping.