Think extremities. Head-Hands-Feet.
I wear a base layer next to the skin that will wick away sweat better than any Cycling jersey- then put on a short sleeve jesey- a long sleeve if it is cold enough and if colder still then a lighweight fleece would replace the Long sleeve. Finally the top lcoat. Must be windproof and if wet- waterproof. But it also has to breath. Have a variety of top coats that will suit any condition from the Pertex that is completely wind proof but nothing else- right up to the goretex jacket that is waterproof. My favourite though is an old Jacket that the inner waterproof liner is falling apart but that one is also warm.
Legs and it will be the Knickers. Long bibs that cover the knees (And it is pronounced Ka-Nickers) Keep the knees warm and that is most of my problems solved down to 20F. Below that or if it is wet- Then I will wear Tights but they are not waterproof- they just keep the cold water from directly stinging the legs.
But the extremities. Head and I wear a ski mask. Gloves and feet and I wear Sealskinz waterproof socks and gloves in winter grade. Keep the hands and feet dry and out of the wind and they will stay warm. And extra protection for the feet are the Shoe covers that roadies use a lot. They do keep the wind out and most of the wet.
Don't mind winter riding but with all those clothes on-I feel like the Michelin man at times. It does take a bit of cycling energy away from me so I expect my winter average speed to drop a bit. But I would rather get on the bike and ride than sit in the garage on a trainer or down the Gym.
Edit-Just so you can realise that some of us do get out for "Fun" rides in the winter Attachment shows me earlier this year up on the hills. No shoe covers as they don't work well in mud or Snpw- but the tights and the "Old" warm jacket are there. And it was cold when I stopped. Riding and warm enough.
And we don't get snow very often in the S.E of England but this year we had a good covering for a month or so. Just hope the next lot comes in another 5 years time.
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