We asked experts in the boot-making business about the best ways to break in a new pair of leather boots—whether work boots, cowboy boots, or Doc Martens.

Let me emphasize: Hiking boots should never hurt, not even ones fresh out of the box. Hiking boots might feel a little stiff (that's why you need to break them in), but pain is a bad sign.

Breaking in leather boots begins with getting the right fit. If a boot is too small back-to-front or too narrow in width, no amount of breaking-in can make them comfortable.

Break in the shoes at home before lacing up for the track or trails. Wear them for short periods at home or around the block to allow the feet to adjust to the arch support and heel drop before ...