I have two pairs of these shoes (size 8.5 and 9), and I find the 9 more comfortable. I usually wear other Keen shoes (Targhee) at 8.5 comfortably. I like the size 8.5, but I sometimes get a bit of pain on the top of my foot (only my right) where the laces are if I wear them for a long time. Thus, I bought a 9 because I wanted to make sure this was not an issue for a 8-day hiking trip in Montenegro. As for durability they are holding up pretty well after 2 months. Montenegro hiking was a good test because it very stony, which put a lot of stress put on the sides of the shoe (think of stepping on somewhat slippery fist-size round limestone rocks for hours). As for the weak point of Keen shoes - which is the outer toe area for me. I can see visible wear (see picture), but the waterproof layer is still intact. My previous experience with Keen shoes (Targhee 2 and 3s) the waterproofing wears out in this area first, then outer layer of the shoes starts to rip. Not sure if it's my foot or the way I walk, but I usually use it as a measure to see how good the Keen shoes are. Overall, I really like the design of these shoes. They feel more comfortable compared to the Targhees and so far they are holding up. I would recommend these shoes (and I would recommend hiking in Montenegro too!).