They are comfortable right out of the box--no "breaking-in" required. That is why I purchased these boots a second time. However, the heels wear down really, really fast--and these boots were not being used for heavy labor or riding (like my other boots that I have to break in. The heels are just not good quality--they were wearing down immediately just from casually walking around (the heels wouldn't last long at all on the ranch, doing work). I should probably give fewer stars--but they are so comfortable that I am rating them higher than they should probably get. Just don't buy them for riding or ranch/farm work.