When you measure your calf for riding boots, I assume you should flex your foot so the calf muscle pops.

Once you have this measurement, do you then look for boots with at least that large of a circumference, or do you go for a bit smaller for the stretch element so it keeps a good fit? Or, do you look for a bit larger for jeans and such?

Not that I think I would wear boots over jeans as I primarily want them for skirts, but the option might be nice.