Use your blow dryer to heat up your shoes for several minutes before putting them on your feet. Also try an insulated insole to go between your foot and your cleat.

I ride to work, unless there is to much snow (don't trust the cars, and can't see the curb). I find I need the booties to keep my ankles warm, but they help the feet too, but not nearly as much as heating the shoes up before I put them on.

When I get dress, I look at the thermometor. 25, I wear a short sleeved shirt, long sleeved shirt, fleece jacket and rain/wind coat. at 19 I put another long sleeved shirt on.

Always have bike shorts, long heavy tights, (two pair at 19) and rain pants for a wind break.

Polortec balaclava, with an additional bandana and earband when it is extra cold. Wool thinsulate mittens, with possible another pair of stretchy gloves inside.

I am not riding really fast, cause of the studded tires, but I manage to stay warm.

Also have an inhaler for the asthma thing. Keep you mouth covered in colder weather. Colder is subjective, depending on what you are used to.