In a new boot, you should have roughly 1/8 inch slip in your heel and a snug feeling of the leather across the top of your foot. Through wear, the heel structure of the boot will soften and eliminate the slipping feeling, and the leather across the top of your foot will stretch and conform to the shape of your instep. It is important that a new pair of genuine leather boots be as snug to your foot as possible in order to allow them to stretch to your foot shape. We recommend these steps to aid in getting a rigid boot on for the first time: ✜ Make sure that your feet aren't hot or swollen from a long day standing/walking. It is best to try on new boots in the morning. ✜  Wear thin socks or even nylons the first few times you wear new leather boots until they stretch and conform to your feet. ✜  Stand while using the pull tabs and pushing your foot into the boot. It should have a nice “pop” feeling once it snaps on. ✜  Twist/roll your foot to get through the instep. ✜  Work at it for a few minutes, taking breaks if you need to. Once you have your new boots on, please remember that it will take time for leather to stretch and conform to your feet.  The softer the leather is, the more it stretches.  If you’d like to speed up the stretching process, make sure to soften the leather with a good conditioner, like Black Rock Leather & Rich.