Two pairs of thick socks with toe warmers between them, MTB sandals *. That gets me about 2 hours down to about 30ish.. I usually don't ride that long under that. Regardless of what I am wearing, what I've found that works best is an hour in or when I feel some numbness in my toes, I wiggle my toes up on the upstroke and down on the down stroke every few minutes to "wake them up", the numbness goes away and warms them up some. Those toes are just sitting there going along for the ride, get them involved and some reason for some additional blood down there! I've done it enough that I don't even have to think about it and can just do it, even at a decent 90-95 cadence. I've been to ball games in the stands at arctic temps with some really nice super winter boots and thick socks but even then, with no motion down there, it gets frozen. Bike riding is not much different. My experience with socks is... I've tried probably 20 different types over the last three years. Wool seems to be slightly better and what I use but its not much better than others for pure cold feet unless there is some heavy moisture component involved.
* MTB or regular sandals may sound like a dumb idea but I wear them year round on the bike. Warmer, cooler, and dryer than my regular MTB shoes, you can wear various amounts and types of socks, covers, bags, and whatever you feel you need based on conditions.
Last edited by u235; 12-23-18 at 09:46 PM.