Granted these are my first high quality boots. I took me around 3 weeks of wearing them to break them. I used leather conditioner inside and out to help soften these up. The heel was a very hard rub for me and is what took the longest to break in.<br />I have been wearing them for several months now and have them on my close to 16hrs a day. They have become very comfortable. I do have my left boot's tongue that slips down and is super annoying. Guess ill have to get it sewn to correct that.