The uppers of your Chisos boots will last decades if you take care of them. Condition the leather about once every three months. The leather soles are designed to wear out and be replaced, much like the brakes on a vehicle. Expect them to last 12-18 months under regular use—wearing every other day to allow them to breathe and avoiding exposure to water and excess moisture. To extend the life of the leather soles, have a cobbler apply a rubber sole saver (about $30) upon receipt. A full resole from a skilled cobbler should cost $150 or less. These steps will ensure your boots are ready to hand down to the next generation.