I wear some modest heels, but mostly just at the office, where I don't walk around all that much. Otherwise, most of shoes are flat or have a wedge heel, and I change out of my heels to walk to and from my car. I hate walking more than a block or so in heels and I hate driving them in about as much. During the winter, I wear a lot of skirts, with tights and boots, but the boots get swamped out for some Keen Venice sandals for my walk to and from the car. I look like an idiot wearing those shoes with a dress skirt and tights, but I don't really care. They're comfy and easy to drive in.

Beyond the above example, I've never felt like I had to choose between sensible and chic. There are SO many cute flats on the market; it's just a question of finding ones that offer good support and fit, while still being cute (or at least cute to me). I'm about to place my first shoe order (beyond mountain bike shoes) in about three years (yes, my shoes are looking pretty rough these days). I have one sporty shoe, one casual flat sandal, two dress sandals with a modest wedge heel, and a pair of dressy shoes that I need for a wedding I'm going to.