How cold are we talking?
I rode all last winter, and while we definitely felt the effects of global warming here in Vermont, I rode many days in temps below 20F. I know you'll read most places that "you usually don't need more than one layer for your legs", but for me, if the high of the day is below 25 I am likely to wear two layers on my legs. I have a pair of heavy weight Craft pants that were great -- I think TE may sell them -- they are very heavy fleeced lycra with wind/waterproof panels on the quads, and they have a little extra room for layering (but still fit more like tights than like pants). If it got really cold I would layer a pair of light or midweight long underwear under them. I also had a pair of Hind Arctic pants that were good for really cold weather -- also in a cut that had a little extra room for layering. For temperatures over 30, I think I usually just wore regular tights.
I wonder if it would help you to warm up your muscles before you go out for your ride? On a trainer, or rowing, or even taking a short jog, whatever you have access to? Or just leave yourself a little extra time for warming up on your ride? For me, it did take me a little longer to warm up on cold days, both my muscles and my lungs, but once I was warmed up, I was fine -- I didn't find that I had difficulty staying warmed up. I didn't find it affected my speed, cadence or gearing significantly. Maybe it would be better for you to focus on shorter, more intense workouts (making sure, though, that you warm up well first) in cold weather, if you are having trouble staying warmed up?
Also, don't discount the importance of keeping your torso really warm for keeping your legs warm. If your core is even a little cold blood will be diverted from your extremities to your core to keep your organs warm, decreasing your performance. In really cold weather I would usually wear a lightweight long sleeve baselayer, followed by a heavyweight midlayer, followed by 1) just a fleece vest if temps were moderate 2) just a windproof jacket if the temps were colder or 3) both a fleece vest and windproof jacket in really cold weather. In REALLY cold weather I'd trade the lightweight baselayer for a midweight baselayer, keeping the rest of the system the same. The coldest day I rode started at about 4 deg and got up to a high of 10. Covering your face is really important at that temp and I had to switch from sunglasses to ski goggles because even my vented sunglasses would completely fog up at every light and then, because the air temp was below freezing, the condensation would freeze -- so I just couldn't see at all -- eek! But other than that, I was fine!
Hope this helps!!! Good luck!!! It can be really fun to ride in the winter if you can get past the psychological barriers (that's the hardest part for me anyway, because believe it or not I REALLY hate the cold).



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