I started cycling a lot this winter and I think I am getting it down pretty good. I am a bit unsure at when I need a balaclava and goggles vs a skull cap, neck gaiter and yellow tint sunglasses. I tend to error on not using a balaclava cause I hate it but it does work a lot better. I usually just have a spring windproof jacket, fleece layer and then either a t-shirt or a long sleeve insulated shirt. I then wear hiking pants and sometimes long underwear. All works pretty good to about 10F. I find feet and hands always still get cold. I just bought a massive pair of boots to cycle in that are one size larger. This with toe warmers and wool socks seems to have done the trick. I use mitten liners and over mitts. I always end up still pulling my thumb into a fist to try to warm things up. My core is never an issue - always warm and I don't feel a lot of cold in my legs. My head at the start of the ride is cold but that always gets better mid ride.
I am kind of worried that as temps go higher though I will cook myself..... Or not hit the right temp to drop the ridiculous sized boots. Boots just slide on - so easy. Cycling shoe covers with multiple socks is a pain. So long to get ready.