I've worn military uninsulated boots. Put on a pair of woolen socks when it got colder. Got them at good prices.
For the real wintry cold I have an old pair of Sorel Sno Pak boots, and a close out pair of more "modern" fully rubber insulated boots.

On winter hikes, I started wearing wool gaiters over low cut hiking shoes with wool socks. I use a heavy duty silicone spray (auto stores) to cheaply waterproof the hiking shoes. And they are not the $70 gaiters. Found the gaiters in an army surplus store.