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.
"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."
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.
Canfield McNish said that the more shoe between the ball of your foot and the ground, the more comfortable you'll likely feel while wearing them. There's a lot of pressure on your foot when the only thing separating it from the ground is a thin sole (plus a non-slip pad, of course), but some of that is relieved when your foot is more cushioned, like it is with a thicker sole.
High heel shoes are very common footwear for women. We wear it at work, in school, when we’re hanging out with friends, and basically everywhere. Sure, sneakers and flats are comfy but high heels just give us that much-needed confidence to do what we have to do. Admit it, wearing them sometimes cause pain and blisters and no woman is immune to that. It’s good that there are hacks we can do to lessen the pain. Are you ready? Here they are.
This secret to reduce pain while wearing heels is so good, you’re going to want to share it. Woman’s Wear Daily recommends taping your third and fourth toes (counting from the big toe) together to alleviate pain from wearing high heels. Sound crazy? The proof is in the science: there’s a nerve that splits between those two toes, which causes pain when pressure is put on it (like when you wear heels). The tape helps to remove strain on the nerve. 
It turns out that it's not the length of your heel that's the most important factor in comfort, it's the width. Many high heel lovers turn to a wider heel, like a block heel, to distribute their weight and walk on sturdy support. Try the Motola Heel from comfortable brand, Born. You can walk down the street or stride around the office with comfort and confidence!

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.
You need to take regular intervals to save you from the pain of wearing heels, no matter how good the quality of your heels is. You need to bring out your legs from the heeled shoes once in a while. You can take regular breaks after every 30 minutes if you suffer from severe pain because the breaks will let your feet breathe and shoo away the pain.
Have you ever noticed how frustrating it is to deal with your feet slipping out of your heels the minute they leave the ground? Even worse, loose shoes often make you drag your feet in an attempt to prevent them from falling out. Heels with straps, ties, or buckles over the ankle or feet offer a solution. Go for adjustable straps to accommodate swelling.
These 18 hacks, tips, and tricks will succeed in making wearing high heels a better experience – and they may even change your most painful heels into something resembling comfort. Unfortunately, some heels will never improve, but that doesn’t mean you can’t try! You need this info right now especially, with the holidays around the corner. Here are some tips on how to make your heels more comfortable:
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.
Do some foot exercises and stretching. These exercises will help your nerves get more flexible and take the next heel day attack better prepared. The stretches that you’ll want to do are the stretches that will target the front of the foot and ankle, like pointing your toes down and pulling your toes up with a strap to get the Achilles’ tendon and the calf muscles. And then side to side to get to the instep and the outside of the foot.

You should always choose heels with thicker souls because that will ensure that you have enough ground to land your feet on. The ground will give you ample space to your feet and you will feel comfortable walking in them. Your legs can be hurt by thin soles because they put more pressure on your feet and dirt and other external agents can get into the legs and make your feet dirty and cracked.
Sure, those strappy, skinny summer stilettos may look like a dream. However, it's important to be realistic about what kind of shoe has day-long potential. A thin sole will most likely cause pain for the bottom of your foot. Look for something with some rubber on the bottom to provide a bit of a buffer. Ideal? A heel that has a bit of a platform in the front. The platform reduces the incline of your foot, making things more comfortable all around.
I may be a hardened heel advocate, but the lower foot pain in this case just never seemed to be worth the payoff. However, I’ve come to swear by one very cheap, slightly weird-sounding, simple trick to avoid that dull pain in the balls of your feet. You know, the kind that comes from attempting to wear anything taller than three inches with a heel thinner than a pencil for more than two hours straight. 
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