I just started biking last March, so I am only a bit ahead of you on this. I found it tricky even in the spring, because you sweat quite a bit, but then you cool down on the downhills.

Shoe covers (Neoprene or some other synthetic stuff) made a big difference - I'm sure there are non wool warm sox. I just got an excellent pair of lined biking gloves.

For the in between weather last year I work bike tights without a chamois over bike shorts, which worked pretty well. I just got arm warmers and leg warmers (Decente) to help with the transition season this year.

For the top last spring I layered a synthetic running turtle neck with a fleece top and then a biking wind/rain jacket. I just bought a warmer winter bike jacket on end of season sale.

I think a pair of cold weather tights with a chamois will be needed - would like to hear the suggestions on those.

Also, I got a poly skull cap for under the helmet which covered my ears, but I suspect there are better head gear options out there.

Looking forwar to the usual TE helpful advice on this one -- thanks for asking the question