When you wear a high-shaft boot with a shorter skirt, always wear tights, not sheers, to complete the look. You can wear short boots with a short skirt if you wear coordinating tights to lengthen the line and to tie the boot to the skirt.
Consider camel and brown boots instead of black. They are a good match with the tweeds and equestrian styles.
Boots with a bump toe, a platform sole or heavy heel should be worn with a wider-leg pant.
Dress boots should be worn close to the ankle with tighter-fitting pants. They should have a slimmer heel, not a chunky design.
Shoe boots are excellent choices for denim, jeans and slacks.