I was planning on wearing these in New York City during winter. The shoes seem well built. It feels very snug and warm. However, I mistook them to be tight earlier. I do not think that I will be wearing woolen socks while using these shoes. Also, I am unsure of how the elastic sides might hold up especially during wet conditions. In addition, it might wear out at a different rate then the leather. I almost cannot imagine wearing these in warmer climates such as Southern California or Florida or even North Carolina. I expect this to last me at least two seasons. If it does not, I will update this review.