I can tell what is NOT a good combination. Don't use a boating paddle jacket as a cycling rain slicker... EEEWWWW!!!!

Each place will be a bit different. We have a lot of winter weather in the 30's and 40's. Occasionally down to the mid 20's at night.

I'm usually good with just a single layer of fleece or sweater + cycling jacket. If it gets cold, I zip up. Warmer, I open it a bit more. I do like waterproof ski gloves, but don't get too excited about warmers.

Good weatherproof winter cycling shoes are great.