Ice Ice Baby: The key to stretching your heels to be slightly more comfortable is sitting right in your kitchen! By filling plastic bags with water, putting the bags inside your shoes, and placing the shoes in the freezer, the water will expand as it freezes and stretch out your heels. Just make sure there is no air left in the bags before you seal them tight. Seventeen suggests keeping the shoes in the freezer for 4 to 8 hours, and then "let them sit at room temperature until the ice thaws to a point where you can slip the bags out of your shoes."
Consider a lower or more comfortable style. Choose a thicker and more stable heel like a platform, wedge, or chunky heel to provide more support and weight distribution. Shy away from pointed-toe styles if you have wide feet or toes, opting for round or almond-shaped instead. You can also buy heeled boots or heels with ankle straps to help support your ankles.