I can tell you what I do, but it may a little different for your situation because we don't get much snow here in Texas.
This morning it was in the low 50's and I put a sweater on Sassafras before we went out for our walk and she did fine. It helps when the wind is not blowing and the sun is out.
Have your pups had all of their shots? When we first got Sassafras our vet did not want us to bring her outside for walks until she fully immunized.
I would suggest you watch your pups closely for any discomfort, like shivering or shaking. Often they let us know quickly if they are uncomfortable.