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.
Rough up the bottoms of your heels.[5] It’s important that your shoes have a decent amount of traction on the bottom. Walking in high heels will be a lot easier and safer if you’re not sliding around all over the place. New heels tend to have smoother bottoms that become rougher once scuffed. Speed up the process by roughing up the bottom of your heels using a piece of sandpaper. Rub the bottom of your heels for a minute or two, or until the bottoms feel noticeably rougher.
Iggy Azalea walked a mile in her Louboutins, but can you imagine what walking even a couple blocks in these would feel like afterward? It's amazing that we willingly wear shoes that sometimes hurt so much, it takes an hour-long ice bath just to recover. And yet, it's hard to ditch high heels completely: They elongate your legs, they make your calves look amazing, and there's something empowering about the sound of your own feet clacking against a hard surface.
There’s a way to walk in flats and there’s a way to strut in heels and never should the two be confused. “Heels are not sneakers — you have to carry yourself differently,” Stempien said. “Use your core muscles and stand up straight. Pretend you’re strutting your stuff on the catwalk and use your hips and legs to propel yourself forward. It should feel more like a bounce than a normal stride. Practice it at home until you’ve got it down pat — this can be one of the easiest ways to avoid pain in heels.”

"High heels may be painful for anyone; women suffering from varicose veins and underlying venous insufficiency are especially prone to discomfort," says Dr. Christopher Hollingsworth, an endovascular surgeon at NYC Surgical Associates. "Veins have a series of series of one-way valves to facilitate the return of blood towards the heart... While veins anywhere in the body can become varicose, veins in the legs are most affected due to the larger pressure from sustained standing, walking or other stress on the legs or feet."
Recently I was at a friend’s birthday where a few of us were debating the plausibility of walking home in  heels after a night of standing around. Now  I love heels, high high heels. In fact the higher the better. I love the line they give the leg, I love how elegant they make me look…..what I’m having trouble with is how they feel. After years of taking ballet and wearing pointe shoes you’d think I could handle heels but lately anything fancier than a sneaker is causing me foot pain.

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.
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