Ah, the Midwest.
In the cool months there I wear my Teva sandal, coolmax liner, wool sock, and then large Seal Skinz over that.
If it was going to stay below 30F all the time, then I don my winter boot (which is lighter than my sandal); and I do that here in Idaho for everyday and backpacking.
I’ve been enjoying my North Face Nuptse boots. I do spray them to help keep them water resistant.
-good luck on a shoe choice,