One hack that might help with walking in stiletto heels is using heel caps. These, usually used to help with walking on grass & cobblestones in heels also work for making walking easier. Because they not only protect your heel points, but also add more surface area to your heels, hence, making your stiletto, much less..well…stiletto-ey! And easier to walk in.
When you walk, lead with your thighs, moving your entire leg forward at once. Think about it: You're probably used to letting your feet lead, right? It takes practice, but you'll find yourself putting less pressure on the ball of your foot this way. And remember: Move your legs from the hips and keep your legs straight. Bending knees looks goofy with heels.
There are many different types of aids to help make a shoe more comfortable even after "breaking them in," and can be purchased at shoe stores, large retailers, and some drugstores. These include special small gel pads for the balls of the feet, heel inserts to help minimize chafing at the back of the shoe and rough patches to glue onto the bottom of a slick sole, affording you better traction.
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Despite the reigning popularity of sneakers and flats, high heels will always be around. And on occasions that do call for heels, you might as well maximize the comfort level in any way that you can. So if you’ve ever hobbled home after a long day or night in heels, this tip for how to make heels more comfortable is for you: Tape your third and fourth toes (counting from the big toe) together—we recommend nude medical tape for a low-profile look, but Scotch tape works in a pinch—to alleviate pain in the ball of your foot. Sound crazy? Here’s the reasoning: There’s a nerve that splits between those two toes, which causes pain when pressure is put on it (aka when you wear heels). The tape removes strain on the nerve, allowing you to dance the night away.