Your daily footwear choices are so important so I took the heels out of regular rotation in my wardrobe. I do love a cute heel, but I can pinpoint the most intense pain I have had as a runner to the start of a new job where high heeled shoes where part of the office culture. I would go for a run in the morning and then throw on my heels for work, encouraging my calves to cramp and shorten up making the next run that much more painful until I ended up in the PT office crying (thank God for Gloria!) because I could hardly walk. This last month I have been very conscious of my shoe choice and it has made a noticeable difference in my recovery time post running.
Be careful to check the degree of the heel on your shoes because even some very comfy casual shoes can have an angle that could contribute to some tightness or pain. Now that does not mean you should wear your flip flops all the time either. Pick some cute but flatter shoes and pay attention to how they make affect your feet and legs. Your runs will be better for it!