Man, that's a lot of gear!

I ride in a pair of thermal tights(The C9 stuff from target), a pair of regular jeans down below. A light wicking shirt, fleece half-zip and rain jacket above(Pit zips open) Headband for the ears, two pairs of socks and a pair of gloves. That's for down to about 20(My current coldest is 22). By 2 miles in, I have the jacket halfway open and the fleece zipped down as far as it goes.

About the only thing I need to work on are my gloves, mine are fine down to about 35 without wind. If it's colder, or windy and cold, my hands are frozen. I also keep meaning to pick up a pair of clear motocycle glasses(Cheaper than the bike version!) to keep my eyes from watering when I'm not wearing sunglasses.

Edit: I will add that the smartwool socks I got for Christmas are awesome, and the best present I got! I stopped doubling up my socks and they stay toasty down to about 30. We'll see how they do come colder weather.