Hi there. based on my limited opinion this is what I can think of.
to stay warm and comfortable in cold weather i usually create a system that is waterproof, breathable, wicks efficiently. For fast wicking and drying I stay away from ANY cotton and use more polyester than wool. now here is the system i use. from bottom up.
Shoe: I use a Vasque trail running Shoe with moderately stiff sole. its Gore-tex and ankle high. it works perfectly for me. Garmont and Montrail also has some good trail/approach shoes with Gore-tex that can be used effectively for this purpose.
Socks: i use a liner socks and a mariho wool (by Smartwool) socks combination. I have three different types of wool socks, light, medium, and heavy weight. I use the medium weight wool socks for late fall and early winter biking. For the coldest part of the winter I use the heavy weight socks. these socks keep my feet dry and worm in almost any condition.
Pants and Base Layer: mid-weight polyester underware and a wind and waterproof pants. I preffer ski pants because of its trim cut and breathability. I also tried mid-weight tights with shi pants and found it comfortable. the tights tend to trap more moisture than the wicking polyester base layer.
Upper body System: 3-layer RULE.
layer ONE: A mid weight polyester or wool base layer (i sometime wear light weight base layer when I go for a long or challenging ride, cause if I ware a mid-weight I feel hot after sometime). I have also used IBEX's marino wool base layer, with great effect. to me Wool takes longer to dry than Fleece or polyester.
Layer TWO: a fleece. a breathable fleece. Wind resistant fleeces are great but they are not effective if you use them under a wind braker or shell jacket. So I just wear a 100 or 200gm fleece (when cold 100gm, when colder 200gm) over the base layer. the breathability of the fleece transfer the moisture from the body and base layer to the outside and keeps the body dry and prevents from over heating. I got great reasult with Polertec fleeces.
Outer Shell: its not the shell that important, its the function that it provides. the features to look for - waterproof, wind proofe, breathable, and effecient in moisture and temperature management. what makes a shell good at water management - pit zips, two way front zips, draw cords etc. pit zips (zips under your arms) help you get rid of extra wormth if you are over heating. Simply open one or both zips and the temperature will pass through it. Two way zips, I sometime over hit even with my pit zips in uphill rides, I undo the fron zip from the lower part and let wind pass through.
Hat: I use a Gore-tex winter hat with neck gaiter. it works perfectly. neck gaiters are great for managing temperature.
this system works perfectly for me in PA, MA and Upstate NY winter. keep in mind that I commute every day all through the winter and when possible (if there is not a ft of snow on the ground) ride in the trails during the weekend.
hope I was of some help to you