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Ankle booties, heeled boots, rugged boots – the seasons go by, and so do the styles. While it’s totally fine to buy a cheap, trendy pair, some of your budget should be allocated to a good-quality pair of sleek leather riding boots. These classic knee-length, no-heel boots originated with the equestrian crowd, and they can see you through season after season. They look amazing with dresses, skirts, and pants, and because they lack a heel, they’re actually very sensible.