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