Let me start by saying that these Timberlands are NOT the painful, discounted shoes that hurt immediately after putting on. If you haven't tried those painful Timberlands then i would suggest that you go to your nearest Timberland retailer and try any pair on sale. After getting hurt by those cheap Timberlands, come back here and give this seller a second thought.
These shoes (Kiawah Bay) are excellent and of premium quality. They are extremely comfortable and you will get what you pay for. I was little worried before buying these shoes that they will be painful like those other cheap Timberlands i tried at a factory direct location but i am glad i was wrong. These shoes look/feel amazing. The soul (bottom part) is hard rubber and not plastic so it looks better esthetically.
There is only one downside i saw which is some what expectable if these aren't your first Timberlands is that the "U" shape stitching on top of the shoes will get worn out pretty quickly. Those stitching are pron to attract dirt and are also easily damaged if not careful. Mine are already damaged but luckily it can be hidden with black shoe polish. I would still recommend these shoes if you are in market for boat shoes or Timberland brand.