I bought the all leather version of this boot. I think it is very stylish, it is very comfortable, and the Vibram sole provides great traction. The break-in period is super short, and these are about ten times more comfortable than the Red Wing Classic Lifestyle boots (model number 8138) that I used to wear in the winter. However, buyer beware, this boot is not waterproof, and in my experience, it is not even water resistant. I think the fact that Timberland Boot Company calls this a "winter boot" is a bit misleading. I assumed this would be waterproof for a few reasons. First, the boot is called a "winter boot," which made me think that I could infer some sort of water resistance. Second, the tongue on this boot is connected all the way up, which is usually done to make sure that water cannot enter the boot. Third, the version that I bought was all leather, and the salesperson at the store told me that as long as I treat it with mink oil they should be able to handle just about anything. I am a fool for listening to her. Anyway, after treating the boots with a few coats of mink-oil, I headed out into the slush and snow. When walking over snow, or small puddles, the boots kept my feet warm, dry, and looking good. However, when I walked through a puddle that was about 2 inches deep, my socks got wet almost immediately. I was shocked. So as soon as I got home I wanted to figure out why these 8 inch boots couldn't handle a 2 inch puddle. I took them off, and inspected them, and I am pretty sure I found the source of the problem. Underneath the leather toe-cap there is a large seam that can let water into the boot. I tried getting my fingers in there to cover the seam with mink-oil so it would be water resistant at the very least. But even after oiling up that seam, when I walk through a puddle that is deeper than 1 inch, my feet get wet. I called Timberland Customer Service to ask if this issue would be covered by warranty. I live in Chicago and Boston, so my winters are always rough, and I need boots that will keep me dry. The customer service representative I spoke to was very friendly, but she said that there was nothing she could do for me. According to her, none of the Timberland Boot Company boots claim to be water-proof or water-resistant. So the fact that mine were leaking does not mean they are defective. In conclusion, if you want a stylish boot that looks rugged, then these are perfect. But if you think you might be trudging through snow, or navigating urban slush puddles, then I would recommend looking elsewhere. I want to give this boot a better rating because it is so comfortable and it looks so cool, but having wet toes in the winter is no fun at all.