I've had my boots for 20 years and love them. They are similar to the ones in this link by the same manufacturer:
http://tinyurl.com/3xbmfa
Rubber, watertight sole. The lining is removable and washable (always a nice feature). My lining is polartec but the one on this site is Thinsulate. I use thinsulate mittens (again, 20 years old) and it's just as good. I only need to wear a cotton athletic sock in these boots. That's how warm they are.
I would also recommend a tightly knit long sweater with a turtleneck underneath. If the knit is tight enough it keeps the cold out very well. Oftentimes, that's all I wear. But I'm a native so don't go by me! Polar fleece is good, too. But make sure it's of good quality. There's some really cheap stuff out there that is not as tightly knit as the good stuff.
If you can't wear wool socks, (they drive me crazy) put a cotton sport sock on first. Cotton absorbs moisture and is more comfortable.
Also remember that if you're walking, you'll generate heat. My kids swear by UnderArmour when they participate in outdoor winter sports. I've never used it. Too tight for me. Supposedly, it "breathes" but I prefer loose cotton with a good sweater.
I find that when my feet, hands and torso are warm, the legs naturally follow.
Now get out and get some exercise! You're a New Englander now!