I've had my Tom's for over a year now and I've worn them almost every other day. They are so comfortable! When I first got them I was a bit nervous about the size. I got a five, which is the size I usually wear, and they felt a bit tight. But since they are canvas, they stretched out to a perfect fit within the first couple wears. They are starting to get a small hole near the tag on the side, but I'm surprised they've lasted this long (as most shoe companies only make their shoes to withstand 6 months or so of regular wear) I've had these things through rain, sand, bike rides, even running! I know some of my friends have a hole in the toe of theirs but if you keep your toe nails short then it shouldn't happen, it also depends on the shape of your toes i suppose. The only thing negative I would have to say is that they start to smell bad if you wear them in rain too many times, I don't have any problem with my shoes smelling bad without socks usually, but the rain did it. Luckily they are completely washable! I put them in the washer and dryer with no problem, just a little shrinkagew hich can be fixed by wearing them.