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The type of riding boots you choose should be determined by the kind of riding you're going to be doing. There are two main categories to choose from: tall boots and paddock boots.
Whether lace-fronted field boots for hunter-jumper events and some three-day events, or plain-front dress boots for dressage, tall boots present a continuous, elegant line of leather from stirrup to saddle. Beyond look alone, however, their fit - how snugly they follow the body's contours - directly affects the rider's control and how clearly commands are conveyed from rider to horse.
Field boots have lacing at the ankle, which allows for some give so the rider is more comfortable riding with the highly flexed ankle that develops from the shorter stirrup length required for work over fences. Therefore, field boots are preferred in all jumping disciplines, including hunt seat equitation, show jumping, fox hunting, and both jumping phases in eventing.
Dress boots do not have lacing at the ankle, and are generally stiffer. They are worn by dressage riders, eventers in the dressage phase, and at formal fox hunts.

The length of your calf determines the height of the boot, while the circumference determines the width of the leg. Wearing the socks and breeches that you ride in, and while seated, measure the length of your calf from the back of your knee to the floor. Tall riding boots will be an inch to an inch and a half too tall when you first put them on. The ankle will soften and break in, and with use will begin to wrinkle, or drop. Field boots tend to drop more than dress boots, and boots without a zipper will drop more than those with a zipper. A well-fitting pair should actually feel too tall at first, rubbing against the back of the knee. Walking around in new tall boots with the zipper 1-2 inches down will help the ankle to break down without being quite so uncomfortable in the back of the knee.
The calf of the boot should fit snugly, with non-zippered boots being a little difficult to pull on and off. Leather stretches slightly over time, and will break in nicely to provide a custom fit. Zippered boots should be slightly difficult to zip and should be in contact with the calf.
Size charts are provided for all of the tall boots on our site to assist you in selecting the correct calf width (and height, if applicable). If you are in between sizes we generally suggest that you go with the taller height and slimmer calf for the best fit (we find that the width measurements on most of the size charts are on the small side of the range they will accommodate). Boots without zippers can be stretched by a boot repair shop (up to about 1 inch), so the best option for someone who is in between calf widths, or whose calf measurement is wider than the widest available width, may be to purchase a boot without a zipper and have it stretched. You can then have a zipper put in if you wish.
Paddock boots are short boots that come just above the ankle, used most often for pleasure riding and everyday use. Adult riders usually combine them with half chaps over tights or breeches for everyday riding and schooling. Children traditionally wear paddock boots with jodhpurs for show, but also commonly combine paddock boots with half chaps over tights or breeches for schooling.
Paddock boots generally come in three styles: lace front, zip front, and a hybrid between the two that laces up the front for adjustability and then zips down the back for easy on/off (such as the Ariat Performer Zip Paddock). Zip front styles are perhaps the most popular, but riders with especially wide or narrow feet usually find that lace front or lace front/zip back styles offer the best fit.
See these charts for comparisons of different models:
Ariat Tall Boot Comparison
Ariat Paddock Boot Comparison
Or visit our Help Center for more Buyer's Guides and Frequently Asked Questions.