As in my pic, you have to be prepared at all times. This was when we rode our snowmachines in -40 degree weather from Tok, AK to Dawson City, Yukon earlier this year. And no that rig behind me is not an AK style snowmachine. It's the only means of transportation to Chicken and Eagle AK and Dawson, YN, other than snowmachines.
As for riding in cold weather, we are hardy folks up here but not dumb.
If you are limited in what you can wear under your protective riding gear, I strongly suggest you find either Gerbing or Widder electric vests, pants, gloves etc. work best. I have already used them on my Busa this fall. (our temp is starting to come down)
Actually as I let go of one of my tourers this year, I've had to make adjustments to my riding gear and it has worked great. You can also buy anti-fog faceshields, decent long underwear, such as we use for snowmachine riding and good wool socks. (yes there are electric socks as well) DO NOT SKIMP on good cold weather riding gear.
Some of my fellow riders even ride in winter (stud their tires.)
Watch the black
It does not matter how slowly you go so long as you do not stop.