1. Fit, fit, fit. If it pinches or squeezes even a tad in the store, it will torture you on the trail. Try on many makes and models—fit differs—and when in doubt, go up a half size.
2. Feet swell, so try on boots at the end of the day. Also, bring your hiking socks to the store.
3. Get quality insoles. Ditch the flimsy ones that come standard and replace them with something supportive, like Sole’s Softec Ultras ($40, yoursole.com).
4. Invest in good socks. They should fit snugly (no wrinkles) and have good underfoot cushion. Great bet: Darn Tough Wool Boot Sock ($20, darntough.com)
5. Preserve leather with Granger’s G-Max Universal Footwear Waterproofer ($10, grangers.co.uk).