Chefisaac: From your post, I presume you're using platform style pedals (i.e. no cleats)? If so, I'd think you probably just need larger boots/shoes and thicker/more layers of socks.

The challenge for me was using my clipless as the temps dip below 30F -- I find the cleat/pedal act as a major heat suck. My solution was larger shoes with thicker insoles. Where I used to have toe numbness in 1/2 hour or so, I can now go an hour or more without my toes suffering too badly. You might consider whether your shoes (and soles) are 'thick' enough (and not too ventilated) as airflow will rob you of heat. likewise, not all wool socks are equal; thin wool (or silk) socks are intended (generally) as an under-layer or liner sock, to be used with a thicker loft/insulation layer when the temps drop.