One day, I want a fancy cycling jacket.

I tend to run warm, so for 20-30F I wear:
wicking baselayer (synthetic)
1/2 zip merino wool cycling jersey
wicking high-viz long sleeve top over that
merino wool buff for my neck.

And hat/earband, gloves, shorts/legwarmers--and an overpant if it's really cold.

I have those Columbia OmniHeat boots that are lightweight, waterproof, and excellent. They are too warm for temps over 30ish, so I only bust those out when it's really cold. Temps in the 40s, I wear my summer hiking boots from Ariat.

For the top half of me, that serves me into the teens. Then I add my wool-blend hoodie on top.

I have started using Rapha's Winter Embrocation, and that stuff is amazing for knees, neck, and lower back. It's like wearing a heating pad.