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Sierra Trading Post Tip: What makes a good hiking boot? The first thing to check is the bottoms of the boots. You should not be able to feel any stones through the soles. Hiking will involve rocky terrain, and over time, rocks and stones underfoot will cause pain. Hiking should be recreationally pleasurable as well as being a great way to get good exercise. Therefore, a solid bottom to your hiking boot should be at the top of your list!