Historically people have ridden horses in their everyday clothes and footwear. The riding boot has therefore developed from civilian and military fashions.
The top boot shown on the left, with its contrasting paler top dates back to when boots generally ended above the knee, and were turned down for riding - the brown top mimics the inside of the leather.
Correction - While the brown top does indeed mimic the leather lining, the origin is that the boot was turned UP for riding (the back of the older style boot was cut away, such as those of the Household Cavalry are today), and because of the poor conditions of the roads, were usually dirty when riding was completed. The custom was therefore to turn down the boot upon entry to the home upon completion of riding, so that when one sat down, and possibly crossed one's legs, the breeches did not get covered in mud from the boots - the clean, turned down lining of the boot being the only likely portion to contact the breeches. The outer tab that appears at the side of top boots is the now non-functional tab that was formerly used to pull the boot on. (Many, many thanks for this information).
Riding boots have often been made to measure, and carved wooden boot trees, shaped to the owner's foot and leg, helped to keep the boots' shape. Such boots would be expected to last for many years, and the first pair have been much used and much repaired.
To fit well when mounted boots are usually quite close-fitting. Boot pulls such as those below are necessary to pull them on, curved "boot jockeys" help the leg to slide into the boot and assistance or a boot jack or both are used to remove them.
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