Fashion guidelines for Western style boots?

I have some black knee length ones (Mark Nason Siren Concordia) and some brown ones that hit mid-calf (Old Gringo Cruzadas). What are the guidelines for wearing boots with long and/or short skirts? And what about jeans - when is it OK to tuck the jeans in and when should the jeans go over the boots? Is it OK to wear the shorter calf-length boots with my skinny jeans tucked in and can I wear them with a skirt?

Fashion guidelines for Western style boots?
thats not my style, but my friend goes to a place called Skips for her boots, its a western store



Hotel Silvota