I just hit the one year mark wearing these boots. I am tempted to buy them again but not for the comfort factor. I still think this boot is the best looking steel toe work shoe I have seen and I've looked at a lot of them. Style and weight are the main reasons why I purchased it a year ago. Even though this is a higher topped shoe, it is considerably lighter than a Timberland low-top shoe I had previous to this one (The Titan).  And that is a contributing factor of why I would purchase it again this year. The other reason I am considering it again is durability. The stitching, leather and everything about it on the upper has held up well...really well. I think the sole has a little more wear on the heel than I would expect but it hasn't fallen apart, worn down so much that is smooth/slick, started &#34;flapping&#34; or anything like that. In other words, if the upper would get me a couple years, which I think it would, it is doubtful the sole would.  As far as comfort? These boots are not really comfortable. To be fair, there are very few shoes I find comfortable, so part of that is me and part of it is the shoe. There seemed to be a couple of hot spots in the foot bed. I knew this going in and knew I would need to put an orthotic in the boot—which I did—a $30.00 orthodtic. This made the comfort level tolerable.  Another thing to consider, depending on where you live is: This is a hot boot. I live in SW Florida, so hot boot is not necessarily a good thing. All waterproof work boots may be hot, I don't know. I know I appreciated the warmth of the boot this past winter but haven't been too fond of it this summer. As far as waterPROOF goes, I don't think so. It is very water resistant but not waterproof. I have spilled/poured water a couple of times right on the area where the tongue begins and got a wet-ish foot. I have no complaints with their waterproof claim, however,  when it comes to walking through puddles, wet grass, etc. They perform well there.  I get a boot allowance from work of $100.00 per year (or as needed). If I didn't get that, I doubt very much that I would have bought this boot, considering I have to add the orthodic just to make it comfortable. Again, some of this dissatisfaction is probably me. Will I buy it again? Probably not this year since I since I have a considerable amount of life left in them. I cleaned them up and oiled them yesterday and they still look pretty dang good. I think this year I will go with a Keen brand shoe that I tried and liked. It is a low shoe-type steel toe. I wanted to have a lighter shoe that I can wear the times when I have inside work and have these boots for rougher outside type work. I would say I work 50/50 inside/outside. If the Keens hold up well this year, I will probably buy these Dunhams again next year to try and maintain a couple pairs of shoes to switch off with. If they were more comfortable, lighter, cooler and closer to a hundred bucks, I would buy them right now!