Tall, fitted boots that reach above the widest part of your calf range in type from rugged Western-style riding boots to elegant, high-heeled fashion statements. With fitted boots, it is not enough to make sure the shoe part fits correctly. The way a boot should fit around your calf is pretty much the same for any boot. However, an improper fit of the upper part of the boot won't look right. Worse, once the boot is broken in it won't fit correctly.
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Measure your calf size. To start, sit with your feet flat on the floor directly in front of you. If you plan to wear heavy socks or wear the boots with trouser or jean legs tucked in, measure your calf while wearing these items.
Wrap a tape measure around the widest part of your calf and record the circumference (distance around your calf). Measure your calf to the nearest centimeter or one-quarter inch. Repeat the measurement for your other leg and use the larger of the two measurements as your calf size.
Try on boots that match your measured calf size. Because styles vary so much, the final test is the actual fit. In general, fashionable boots such as women's high-heeled boots should fit snugly around the calf and have no more than one-quarter inch of space between your skin and the boot at the top. For heavier types such as riding boots, the boot needs to be snug to the point of discomfort when new. The leather will stretch as the boot is broken in and gradually become more comfortable.