I have some damage in my toes from various injuries, so I'm not very comfortable in shoes with a heel. I would say the most comfortable heels I have are Cole Haan Air Talia mid pumps. However, I wanted a shoe that was a little more covered and a little less serious business, while still looking somewhat professional. These seemed like a good choice, and so far they are. I can't wear them all day without suffering a little bit, but less so than most.