I have diabetes as well, and cold is tough. I bought some pac boots from Cabela's some years ago that are rated to -85 degress. I also stole a pair from my son rated to -40. Non diabetics will consider this overkill, but it is not. With the -40 boots, I lost feeling in my feet at about 25 degrees. I do not walk, but, rather, I sit on a stand all morning. I am just not sure a diabetic is ever going to be totally comfortable in cold weather. I have accepted this as a fact of like and seldom hunt in the colder weather, which is odd, because when I was younger, I like to hunt on mornings so cold that most folks didn't want to be out..