Military boots are not only functional in their durability, but are also a fashionable style that shows no sign of fading soon. Whether your boots are genuine military-issued or replicas, you will have to spend some time breaking them in. Made of durable leather, they will need to be softened and given a chance to conform to your feet, but once they do they will last for years and be ideal to wear in inclement weather. While some methods suggest soaking the boots in water, the most tried and true way to break them in is wearing them.
Get a good fit at the store. When going to buy your boots, wear the socks you plan on wearing with your boots. The boots should fit snugly and have a minimum of 3/4 of an inch of room at the toe.
Make sure your boots are the right size. Once you get your boots home, try them on and wear them indoors for a couple of hours. Make sure you wear them on the different surfaces in your home, such as carpeting and laminate. If the boots don't feel like they are the right size, return them and repeat the process until you find a pair you are satisfied with.
Bend the leather. Flex the leather of the boot as much as you can by bending the boot between the heel and toe. Loosen the laces on the boot to your comfort level. You may want the laces loose at the beginning before the leather is broken in.
Wear your boots out and about. The real process of breaking in a boot is through wear. To minimize your discomfort during this time, wear them out for short times at first and then increase the time you wear them. For example, the first few trips might be to the grocery store, the next might be a walk or concert and finally you will be able to wear them for as long as you like, in any scenario.