For the winter I don't worry about jerseys much; back pockets are useless if you have a jacket over them. Instead I mostly wear a coolmax tee, LS if below 20F/-7C, topped with either a light Merino sweater I got at Costco for $20, or if it is very cold (below 10F/-12C) a polarfleece jersey from Old Navy, passed on by my duaghter. Most of the time I wear some Dryfit pants from Moving Comfort that happen to be available in short inseams. Cycling shorts under that unless it is so cold (below 5F/-15C) that I want to wear longjohns as well. Too many layers in the crotch just gets uncomfortable. Feet are 1 or 2 layers of thin Smartwool socks until it is down to 5F, then I go with a heavier pair of snowboarding socks. After November, when I switch to my Snow & Ice bike, I give up my clipless pedals and use some of the MTB mini clips (no straps) and a waterproof pair of insulated boots. Under my helmet I wear a very thin coolmax beanie most of the winter and add a Balaclava below 10F. This winter I will be trying an EMS techwik hoodie as a base layer. Handcovering is the most individual aspect. My hands are arthritic and get cold very fast and stop working. The first stage of the winter I wear wool gloves with leather overgloves. At about 35F2C, I switch to a pair of PI lobster mitts, however, I absolutely must have liner gloves with these. Other wise they are no warmer than my pair of $8 WalMart hunting gloves. When it is below 5F, I switch to heavy wool mittens with leather "chopper" overmitts. These are clumsy, but they are the warmest. Usually, around 10F, depending on the wind I switch from glasses to ski googles. I have never covered the vents on my helmets as I sweat too much on my head and need to let that escape. The final layer of course is a windproof. I use a Jackson-Gibbens jacket because it gives good wind and water protection but is well vented, and was cheap. I also use my O2 jacket well into the fall, down to about 40F/5c.