I have Sidi road shoes and I can wear Woolie Bully socks comfortably. I just leave the ratchet thing and the velcro fasteners quite loose. I wear those socks with Neoprene booties down to about 40 degrees. This week I went out and rode with temps in the thirties for the first time. I used the chemical foot warmers and it was heaven. Basically, I dress the same way i would for x country skiing. I also wore my longer smart wool ski socks, which are thinner than the woolie bullies, and helped to insulate my legs a bit.

Does anyone else have difficulty shifting and braking in lobster gloves? Mine are extremely warm, but I feel really restricted in which fingers I can use, so I've ended up taking them off and switching to my Am-fibs, which are almost as warm, but not quite. They were expensive, and now I think I may have wasted my money.