In the PNW our winters are mostly cold and wet, just above freezing, so it's tricky to dress for if you're planning on going on a workout ride. My only solution has been to throw money at the problem, unfortunately. I blew a shitload of money on Q36.5 gear (Termico gloves, Long Salopette bib tights, R Insulation Jacket) and am incredibly happy with it, as lets me go hard in wet near-freezing weather without overheating or feeling cold, something I've never experienced before. Usually my base layer is a lightweight merino turtleneck, and I wear some generic Pearl Izumi booties over my riding shoes, and some thicker wool socks. I wear a nice custom merino cap under my helmet. I really should see if that guy can make me another one of those caps.
For more casual rides, I have that same merino base layer, and I pair it with a heavy leather motorcycle jacket, the above gloves, midweight jeans, motorcycle boots, and a bandanna to protect my face. Works well enough if I take it easy, otherwise I'll overheat in the jacket and boots. >>1286894
Merino is fuckin' amazing. The only synthetics that outperform it are fairly esoteric and expensive shit. Icebreaker, Pringle, and some other companies make some great stuff.