So after work I decided to ride down to HighGear and pick up the Cables I had ordered on Team Night. Thanks again, Matt, for being a glorious team liaison.
The ride was nice. The only thing that got cold on me was my quads. The clothing? Top to bottom: Balaclava under winterized helmet, Smartwool longsleeve baselayer, Thermal longsleeve jersey, Lobster Gloves, bike shorts, thermal leg warmers, knicker shorts, heavy duty smartwool socks, and these:
I didn't order the fancy Dura-Ace wheels, but instead, invested (with my too-be tax refund money) in some really good winter wear. I guess it didn't help that, when riding with all my teammates that weekend nearly everyone had these boots or older models. Anyone who has had these said they love them.
So with the clothing listed above, I was just fine. The ride home from the shop got a little chilly since the sun was going down and I had been sitting in the warm shop sweating with all that gear on.
The verdict after a 1.5 hr ride in 20*-15* weather: the thermal jersey is the best winter clothing I've ever worn since I felt no cold on my core/arms, and the shoes may not prevent my toes from going numb since I pedal in squares. My toes started to get cold near the end of the ride, but I suppose that could also be the temps. I'm also wondering if warm legs would have sent warmer blood down to the toes to keep them warm. My quads were the only part that really felt cold, but it was just fine.
So I'm continuing with training outside even in these temps. Sure I'll ride slower, but that's what I'm building now anyway, base miles.