Just a little tip for quickly breaking in new leather boots. Put the boots on and jump in the shower for 10-15 minutes. Get them good and wet inside and out. Wear them until they are dry. The water will soften the leather making them more comfortable on your feet and allowing the leather to stretch more easily. When they are dry they will be perfectly molded to your foot. My favorite boots are my Justin lace up work boots. Good ankle support, comfortable, tough, and not overly expensive. Oh almost forgot, make sure to put a leather conditioner or snow seal on them after they dry. They will last longer that way.