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Kevin McGowan, National Outdoor Leadership School outfitting manager, has five tips for finding and breaking in new kicks. (Take his word—he's helped fit more than 25,000 hikers with boots.)

>> Come prepared Bring the hiking socks you'll wear on the trail to the store, and, because your feet swell during the day, shop in the evening.

>> Run the gamut Try on five to eight pair across a variety of brands. While you're testing, walk up and down stairs and ramps in the store, and think about the overall comfort of the boot.

>> Prepare for lift off You want your heel to rise inside the boot about a quarter inch when you walk. (This allows space for your Achilles tendon to stretch, but isn't so roomy that your heel rises too much.)

>> Give yourself wiggle room Kick a wall with the front of the boot three times; this simulates hiking downhill, which is hard on your toes. If the shoe is too short, your toes will jam into the front of the boot on the first try. Conversely, if the boot's too big, your feet will just slide back after multiple kicks. The ideal fit will take three jabs for your toes to hit—and stay—at the front of the boot.

>> Get outside, but go slow To avoid blisters and achy feet, break your new pair in with mini hikes, starting with one mile and gradually working up to a few miles.

Before you head to the store, check out our favorite hiking shoes.

Go back to the Ultimate Hiking Guide

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