Some shoes feel comfy when you first put them on, but after a mile on city streets become excruciatingly painful. These Drew maryjanes were the opposite. When I first put them on they threatened to bite into my tender Achilles tendons and the sides of my feet. I almost returned them, but they looked so nice I instead protected my Achilles with moleskin and took them out for a test flight, where they exceeded my expectations. Once I got walking, they eased up. The fit is close, but they never actually chewed into my skin or gave me blisters. They come with orthotic inserts and have extra toe room (but don't look like it) and I returned from my test walk with happy, unmaimed feet. These are the best compromise I've found between dress shoes and walking shoes, which I need in New York - even in a dress, I have to make it to and from the subway on foot.