I agree with wicking base layers. Make sure for winter, you're getting ones designed to be warm, usually made of a synthetic materal and especially look for "microfleeced" or "fleeced" in the description. Those go a long way.
I also agree with "buy once, cry once". Just bite the bullet and get heated gear, even if you have to buy it one piece per year, it's worth it. I put it off forever, just wearing multiple layers (microfleeced warming base layers, jeans, t-shirt, wool socks under cotton socks, thermal long sleeve shirt over t-shirt, vest, heavy winter jacket, leather overpants, warming sports gloves under leather gloves, etc).
Now with heated gear (I have First Gear heated gear, same gear as Warm-n-Safe, actually is made by them, even says so on the tag licensed to First Gear from Warm n Safe), it's way better. For one, all those thick layers makes moving around a pita and then if you stop in some place, you're boiling inside until you get back out riding. And then you're still cold at those temps (just less cold than without all the layers). With the heated gear, you have a lot more freedom of movement and comfort and you're actually warm rather than just "less cold". To be honest, I can't even stand to wear my heated gear if the ambient temperature is over about 55°F as it's too hot even on it's lowest setting, that's how warm the heated gear is. If you do heated gear, don't cheap out on it either with some cheap scAmazon rechargeable battery powered pieces of junk (they'll work, but only for about 10 minutes at which point they'll shut off for safety reasons and you have to stop to turn them back on).
I would add in though, get a sports balaclava to wear under your helmet and get a fleeced neck gaiter. You'll want both of those even with heated gear (or at least the balaclava).