Hello, to give you some previous history I have worn boots since 2003 when I first got into the Army Infantry. I have high arches and have tried many types of boots such as Rocky's, Danners, Altama Jungle boots,thorogood, and basic military boots. Most boots take at least 2-4 weeks of break in and these boots did need breaking in. Most of the new light weight boots take a lot less time in breaking in and these boots took between 1-2 weeks. I had issues with pressure near the outside tops of my ankles (sometimes painful over long periods of time) and decided that it was due to the material inbetween the outside/inside of the boots. I pushed through the two weeks with quite a bit of pain/discomfort, but in the end these boots passed in flying colors. They are light, comfortable, good price, and look really sharp. My last pair of boots was Rocky SV2's which are very impressive boots, but are very pricey (I also didn't get them because i'm in a civilian job where the soles aggressive tread wasn't needed). I am glad that I opted for these boots, and I have read some people that immediately turned them back due to that same issue I had. If you can handle a little pain and a little time these boots are definately worth it in the end for their price and comfort. O yea I also read a bunch of people complaining about the inserts and I can tell you these are some very cushioned inserts and can't understand why people are useing that as a negative. If you have a problem with the cushion replace them with your choosing. These inserts are quite a bit better then the flat boards they usually put into boots. If you can handle a little pain/discomfort and a little time these boots are definately worth it in the end for their price and comfort. I have worn them for about 2 months now and I no longer feel any discomfort in the ankle area.