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Best way to break-in leather boots is to wear them!
usually a boot that is made for riding, bought from your local tack store. I ride in paddock boots and half-chaps, but other's ride in full length rubber or leather riding boots if you ride english. For western you where cowboy boots. Or for either you can save money and just wear plain old rubber boots.
Yes, it is perfectly fine for preteens to wear leather boots as long as they feel comfortable and confident in them. It's a stylish and practical choice for footwear.
as long as they are strong boots
No
It depends on the discipline. In western you should always wear smooth bottom boots so your foot can easily slide out of the stirrup in case of an emergency.
This is the most popular style of riding boot and can range greatly in price. Paddock boots are short boots which come up over the ankle. They can come as lace up, zip up or pull on. You can get these boots in vinyl or leather. With paddock boots you would usually wear a jodhpur riding pant (jods - elastic goes over the boot). Most people choose to wear a ½ chap with a paddock boot - which mimics a tall riding boot. Blundstones are considered paddock boots.
Yes
You might start with wearing a leather jacket and leather boots. (Seriously :) You can wear anything depending on the pants color. If they're black, wear anything. But you'll look better wearing a leather jacket (a color matching the pants) and leather boots (matching the pants).
Leather offers some of the best abrasion resistance. Modern textiles are starting to become just as good.
The best kind of shoe to wear while riding is a boot with a small heel - about 1/2 to 3/4 inch. If you are riding bareback, or on a saddle without stirrups, You can wear tennis shoes, but the heels on riding boots help prevent your foot getting stuck in the stirrup, in the case of an accident. If you are a serious horseman/horsewoman, you should purchase some paddock boots, or perhaps field boots. For those who compete, the best options are dress boots, field boots, or paddock boots WITH chaps. However, there may be certain rules as to what you can wear.
leather boots