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When trying on a new boot you should feel a little bit of resistance when pulling it on. Your heel should "pop" into the boot as you pull it on. Once you get the boot on, your instep should be snug against the leather (like a handshake). The ball of your foot should fall on the widest portion of the sole. Your toes will not reach the end and should be about a thumb width from the end of the boot. Your heel is also going to slip slightly as you walk. Your heel should not rise out of the heel cup but should move a half-inch or less