I live in a rural city. It's pretty common for high school kids to "volunteer" to go shuck corn on local farms. The boot in this picture is a Chelsea, a slip on shoe that's only a boot because it covers the ankle and is generally made of leather. There's a large patch on the side made of stretchy material, and it would be absolutely the worst boot to wear on a farm.

Also, have you tried sock garters? Boots with no socks might be less comfortable than a garter. Though I avoided that problem by just buying new socks constantly

I have what is ostensibly a desk job, but when I was in the Marines, my go-to socks were, believe it or not, dress socks, and inside out so you wouldn't feel the seams on your toes. A buddy turned me on to it and I never looked back. I was always fortunate enough to not have issues with blisters or anything, so maybe I'm just lucky, but a good, calf-high dress sock was my sock of choice.

But my regular life shoe is the Puma Classic, and if I have on short pants, I'll don the lowest possible sock. As some others have mentioned, the rubber grips in the heel are great. But if I'm doing a hike, for example, and wearing boots, even my mid-ankle Merrells, I'll wear a calf-hig sock, no need to play games.