Below is what I found worked best during the 10/11 winter ride season for the 30-40 degree temperature range. The cool thing is all but one of these products remains available and unchanged for the 11/12 winter season. It looks a bit like a Castelli advertisement, but...I truly feel like they make the best tailored and most technically superior clothing out there.
The basics that you need to get by are a winter wool sock, sleeveless baselayer, thermal bib tights, long sleeve jersey, thermal jacket, thermal bootie, winter thermal glove, thermal cap and cover the vents of your helmet. If you'd like to know more about the exact products I use, click below.
Castelli Quindici or Capo Winter Wool merino sock - $18: These were my two picks for 10/11. Both are a thicker merino wool blend and taller to allow for good ankle coverage. If you have long legs like me, sometimes your tights don't quite come down far enough and a 12-15cm tall sock is the best option.
Castelli Core Mesh baselayer- $40: I find this to be my go to baselayer when I don't need wind protection. The mesh material keeps a warm layer of air between you and your jersey, and more importantly keeps the wet / clammy clothing off your skin. I use this same baselayer all summer too regardless of temperature.
Castelli Sorpasso Thermal bib tight - $180: I can't say enough about how well these work. The thermal fabric is great for a huge temperature range. I was skeptical at first because they only come with a sewn in seat pad, however that pad is Castelli's top of the line pad. The Giro++ (Italians say Giro 2) bib straps are barely noticeable as well, they two are taken from Castelli's top of the line Body Paint bib shorts.
Bio-Racer mid-weight long sleeve jersey (must be dutch national team issue or you'll freeze to death) - With a good Windstopper style jacket you can get away with a non-thermal jersey, or even a summer jersey with arm warmers. The long sleeves can be a bit warm when the tempo picks up but you'll be glad to have the extra layer when spinning easily.
Castelli Radiation 1-2-3 thermal jacket- $480: I wear this jacket for pretty much every ride. For this temperature range I remove the snap in radiation panels, which are heat reflective panels that keep your core temperature up. The jacket also has a zip off hood and arms which let you turn it into a vest. It's made from Gore Windstopper and has two huge zippered chest vents that work great for regulating temperature. The three external rear pockets keep the fiddling around to a minimum instead of trying to get into a single zippered pocket that many winter jackets have.
Bontrager Race X Lite thermal bootie - $60: These were probably my revelation product of the season. I'd bounced around getting a pair of winter boots but these pretty much killed that thought, and saved me $190 in the process. The thick pile insulating fabric on the inside provides awesome warmth and the outside water proof barrier keeps the road spray where it should be.
Castelli Pioggia Winter glove- $60: These were the one item I was least impressed with. They have a pretty limited temperature range of right between 30-40 degrees. They tend to be a little on the cold side when it's below freezing and you start to sweat a bit much in them as the temperature closes in on 40. Castelli has discontinued this glove but new models from both Castelli and Capo will be out next season. Sadly, the Pearl Izumi Barrier glove is gone too but they still make the Barrier Lobster version.
Lazer Genisis helmet with (winter) Aero Shell - $200: I rode half the winter in a Giro Ionos with the winter pad kit but switched to the Lazer in mid-February. The Aero shell is the key, this combined with the Radiation jackets hood works brilliantly. The Aero Shell (upper right hand corner of image) basically covers all the helmets vents, keeping wind off your head. Lazer also makes a winter pad kit, complete with ear flaps which would eliminate the need for a hood or hat all together. If you don't have a hooded jacket or jersey, I really like the Castelli Risvolto winter cap or a thermal skull cap if you don't like riding with a bill.