I got these to wear at the office (casual architecture firm) for the summer in Portland. They dress well with jeans, pants, and shorts on my days off. I am happy with the appearance of the shoe, and they are generally comfortable, however after a week of walking in them, I began to notice that my calves hurt when I took them off and walked barefoot. It feels like they have a drop to them...the heel is thicker than the toe. This means your calves are contracted for most of the day, but that's true for most shoes. Really you'll only have a problem if you are used to a flat sole. I also think the side wall is a little low - it doesn't come up much higher than my arch, so it feels like they will slip off very easily. I bought a half size under in anticipation of this, and I'd recommend others do the same.