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Sierra Trading Post Tip: Testing your hiking boots before you buy them is an essential part of the trying-on process. Whether you're an experienced hiker and have always worn Columbia Hiking boots or you're a first-timer looking for the right fit, testing your hiking boot is essential. The first test you will need to perform when buying a hiking boot is called The Finger Test. Unlace the boot, and move your foot as far forward in the boot as you can. With a proper-fitting boot, you will be able to slip your index finger down inside the boot at the back of the ankle. It's important to have extra space in the boot to allow for the natural movement of your foot as you hike. For example, when hiking downhill, your foot will slide forward, so it's best to have some wiggle room to ensure comfort.