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.[3] 

Know your foot type. In my opinion, a podiatrist would be the best way to know your foot type and what’s going on. If you can’t run out to the podiatrist, there’s a couple of neat ways to see if you have a flat foot or a high-arch foot. Wet your foot and step onto a piece of construction paper. When you make an impression, it will show you how much your foot is flattening or how high of an arch you have. You can look at a person’s foot type and see why they are having pain.
Looking for a new take on your basic ballet flat? These low pumps are perfect for spring and summer, thanks to their pink patent-leather upper. Plus, at a height of just 1 1/2 inches, the shoes meet our podiatrists’ standards: “Try to keep heel height three inches and below,” says Dr. Splichal. “For every inch over three, the stress to the foot and body dramatically increases.” 
She also suggested that going for a platform with your high heel, or a shorter heel, can drastically change your comfort levels, explaining: "Choose to wear a height that is manageable, this is pretty subjective, but having a less high heel or a platform sole can make a huge difference to comfort." Anisha agreed, and advised to "get platform shoes that also have a heel under the ball of the foot to reduce the gradient of the foot".
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.

Don't forget the heel taps on your shoes, either. "If you let those start getting to the point where they're chewed up, by the heel, or by just walking on gravel or stone, it's going to make it more likely that you're going to topple over, because if they're uneven, then you're going to be — literally — on uneven footing, so replacing those regularly, before they get bad, is important and that's going to help your shoe last longer too," Canfield McNish said.
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.
Overall thoughts: While I did appreciate the cushion this provided, the pads kind of pushed my feet out in a weird way and made my foot do that overflowing loaf thing on one side. I thought maybe this would've worked better had my shoe been bigger, but as it was, I still had a little room in the back, so I don't think it would've actually made a difference. This definitely made the experience of wearing the heels better since it provided some arch support, but it wasn't a lifesaving experience.
The number one mistake women make would probably be not having the right shoe size for their foot. Your foot size changes over the years, even as much as one full size, especially after having kids. Have your feet sized once a year, and do it if you’ve never had it done. Have your feet measured when you’re buying shoes, for width and for length as well. A lot of people think they’re a wide or vise versa and they’re not, so definitely do that before you shop. 
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