I really don’t feel like visiting an overcrowded waiting room so close to the holidays (especially when the clinic docs are a bunch of blithering idiots), but something’s been bothering me- my little (aka “baby”) toe is quite numb, and has been for anout three days. There is no pain at all, just lack of feeling, and only in the outer half. It looks completely normal, too, healthy and pink. I haven’t gotten my feet especially cold (although I did walk home with soaking boots, but that was a week or so ago).
I have Googled away, but to no avail.
Please, I beg of you, save my little toe before they need to amputate.
(What? I can’t edit my own post? anout! what was I thinking?)
Do you have an attachment to the little fellow? 
That said, the little toe is pretty useless from a utility point of view. Thinking of having both of mine amputated so there is one less toenail to clip. 
Not a doctor, but… Something may be pinching or pressing on a nerve that leaves it numb.
I had the same sensation in the pinky of my right hand. Also, like your toe, it was just the outer edge of my pinky. It turned out that my computer mouse was at just the perfect angle that there was pressure being placed on a nerve way up in my elbow (the “funny bone” nerve) and my pinky was going numb for days on end.
It could be that you’re adjusting your gait a bit and walking funny in the cold or dampness (kinda like the way some peole hunch their shoulders when walking in cold weather) or it’s your boots.
You may try changing the way you lace your boots – I skip a few grommets so that the laces don’t cross of my instep. If I don’t then the pressure across my instep gives me cramps in the bottom of my feet.
Boy - that’s really something that I wouldn’t ignore. Then again, I’m a diabetic, and it would be very very bad for me.
I had the same happen to my big toe and the toe next to it once. Went to see the doctor, and he said “is it numb from about here to here, and are these the toes that are numb?” I said yes. He said “You strained your back”. I guess it seemed a little strange, like if you sneezed and your shoes flew off. So you may have pinched a nerve in your back, but see a doctor (which I am not) to make sure.