These boots are comfortable right out of the box. I bought them a week before a trip to London and wore them while I was in London for 10+ hours a day of walking. I had to put inserts into them, but the fit was very comfortable and didn't really need any breaking in. I bought the Olive colored ones and they are bit more green looking than the pictures show, but they still seem to go with most things. They run big and you should definitely buy about a half to full size smaller. I bought a half size smaller and wear them with thick socks. I could have easily bought a full size smaller and wore them with normal to thin socks. The quality of these boots is great. The leather is very nice and they are very classic looking.