Until I grow pointy feet, I refuse to buy pointy shoes.... (so, never). All of my dress shoes are round or square toed. I also have no desire to break an ankle, so none of them are particularly high and no small heels. They have to be fat enough for me to walk on easily. My work/dress shoes that I wear with skirts are both flats. I have a pair of brown mary janes and a black pair of flats.