In keeping with the comfort theme, whenever I do wear heels out I trust my chunky heeled pumps which can be worn for hours at a time without feeling discomfort. The rest of the time I am in ballet flats and in the winter in sturdy (yet stylish) flat boots.
When you need to be out for extended periods I have learned through painful trial and error that comfort is always your best friend. As a result I no longer ever wear stiletto type heels. Plus I am hardly looking to add height to my frame.