I have a pair of Cannondale Roam shoes that I got two seasons ago. They are great shoes, and I'll be wearing them a long time. They are great with double socks over 30 degrees. My toes get cold but it is bearable. Over 40 degrees is even better. This morning though it was 20 degrees on my 40 minute ride (I'm VERY slow right now, I just got back on the bike).
I tried a number of things today. I made insole insulation with wool and foil. I cut off the toe section of some old holey wool socks and wore them as leg warmers on my calves. I wore Louise Garnaue Stop Zone covers. I thought warm thoughts!
I got to work over 3 hours ago, and my toes are still very very cold. Tomorrow it'll be the big boots and platform pedals. Enough of the freezing!
When I get some cash, I'm going to try electric socks, but I don't know if that'll help the toes out or not.