My doctor insists I don't have Raynaud's syndrome, but I have the most cold-sensitive fingers and toes of anyone I know.
Luckily my lobster mitts keep the fingers warm even at 20 degrees. But I have not yet figured out the piggies. After 30 minutes of riding at temperatures below 45, the rest of the foot feels fine but the toes are cold. I typically ride with cleats (but see below). Things I've tried:
* larger shoes with two pairs of wool socks (one thin)
* larger shoes with one pair of socks to make sure I'm not cramping the toes
* wiggling the toes as I ride
* plastic bags over feet
* felt liners (to prevent heat loss through cleats)
* regular winter boots on platform pedals (i.e., no cleats)
* booties over shoes over double socks
and various combinations of the above. the only thing that works reliably for me is the chemical toe warmers - they are great but inconvenient and a bit pricey over time as I commute an hour each way most days in the winter and use a pair per day (keep them in a baby food jar at work).
I'm wondering whether I should plunk down a couple hundred bucks for the Lake winter boots. they are pricey, but if I could avoid the numbness that would be wonderful.