I've had woody max for several years and like them a lot. They are insulated, however, and IMO would be too warm for Kentucky hunting any time of year if you do any amount of walking. Wetlands would probably be better in Kentucky. They're comfortable to walk in, but they're not a mountain boot. If you want/need a lot of ankle support, buy a lace up boot. None of the pull ons provide much ankle support. I have pretty big calves and the boots in the calf area are snug. I consider that a plus. Provides a little extra support for my legs, keeps the heat in, etc.