Practically no breaking in period at all. Comfortable right out of the box. I have been wearing these boots about a month now. I did get a gel insoles because I am on my feet and walking all shift long but the boots themselves, they are my favorite pair since I can't remember. I have worn and had them all Dr. Martins, Timberlands, all the way back to Sears battery boots. I love these and get many complements on the appearance. Some people's reviews have said that the boots run big, I don't get that feeling. I am a true 9.5 and I am very happy. I am not sure if it is because of the gel insoles I changed or what but they do not run wide or big on me. Would (will) buy again.