This is my 3rd pair of Clarks Wallabee Chukkas. They quickly become my go-to shoe and get a lot of use. On average I'm getting about 5-6 years out of each pair I've owned, wearing them I'd say 4-5 times per week during that time period. I live in a large city as well so I do quite a bit of walking. The quality of each pair has stayed fairly consistent over the years. The only major change on this latest version is that they went from a full leather insole to a half leather insole similar to their desert boots. I've been wearing these for a little over a week now and I haven't really noticed. The leather used on the upper is the same thickness (very thick) and high quality as previous versions. Please note that it takes about 4-5 days to break in the thick leather upper to get it to conform to your foot. Not real pain or blisters during the break in period just slight slight soreness on the pressure points where the leather needs to soften. Once you get through it though these shoes are amazing. They are roomy inside and comfortable enough to wear all day even walking all day. The natural crepe sole is also great if you're on your feet all day standing (think museums etc.). From past experience, the more you wear these the more comfortable they get. The leather on the upper will mold to your foot and so will the natural crepe sole. These are classic boots and have remained slightly unchanged over the past 11 years or so that I've been wearing them.A couple additional items that if you're new to crepe soles will be different. They start off this nice tan color but will turn black and dark with wear. Also the material will pill and sluff off with wear. There is a lot of crepe on these so they will last.