Got these boots on 11/30 and wore them the same night at work. And it was raining too. Very very comfortable and my feet remained dry. Unless you have jacked up feet there is no breaking in process of these boots. Out of the box and on to your feet. Very comfortable during my 10 hour shift. Even showed them off to my co-workers. Going to get another pair If you are in law enforcement or equivalent these Timberlands are a nice boot to have. Timberland has a great name/reputation too so you cant go wrong..