My first year at attempting to ride through the winter. My favorite gear discoveries so far:

Terry COLDweather tights: http://www.teamestrogen.com/prodTY_1817.html
I haven't used them below 30 F yet, but loved them on my 30 degree rides so far. They seem completely windproof. Comfy fleece lining but not bulky feeling. Pad is just right. Price is good too compared to other winter tights I tried (and returned).

Nashbar booties: http://www.nashbar.com/bikes//Produc...2_170081_-1___ Tried these for the first time in 30 degree temps, and they made a huge difference. Great price for a windproof/water resistant bootie. I have 41 shoes and got a medium. Fit easily. Very easy on/off. Not sure how they will hold up since I've only used them once but look to be very well made for the price. (On sale now!) Under the booties I wore my touring shoes with two pairs of light socks (one wool, one coolmax).

Now I just need to figure out my hands and I will be set!