One way to make your heels more comfortable is to wear them in. Wear them around the house, wear them to run an errand, or even for a walk around the block before you wear them all night to a big event. To speed up the process, if your shoes are made from a sturdy leather material, you can even blow dry them! "The heat from the blow dryer can make it easier to break in an uncomfortable pair of heels", says Lexie Nicole, a part time pole fitness instructor. She suggests this to her students: 

For some the higher the heels, the better. For others, a pair of black flats is much more appealing than some stilettos. Whether you're a fan of heels or not, you might find yourself wearing them at some point, so it can't hurt to have some tips on how to make heels less painful. It's no fun to suffer for the sake of fashion, but luckily, if you like to add a little height to your outfits, there are certain ways to do so without stumbling home with bloody calluses and sore arches.
Stilettos are cute but they are not suitable for every woman. Wearing them may make you wobble around especially if you are not used to walking in them. If you cannot do without heels, try to choose thicker and chunkier heels as they offer more support and are more comfortable. However, this does not disqualify you from rocking your beloved stilettos. Do it once in a while and learn how to walk in them appropriately.  
The more coverage you have on the top of your foot, the better. Sometimes high-heeled boots are actually something you can wear all day and they don’t bother your feet as much. In the summer, you can try something with an ankle strap or a big wide strap across the top. If you’re prone to blisters and friction, you might want to try that style, something that covers more of the top of your foot.
Always keep your heels stuffed.[2] Naturally your heels with shrink when they’re not being worn. Since you don’t want all of your breaking in efforts be in vain, keep them stuffed when you’re not wearing them. You can stuff your shoes with the shoe paper and rod that come with the shoes when you buy them. You can keep them filled with shoe trees, which are inserts molded into the shape of the inside of your high heel shoes. Or you can simply stuff them with rags.
Making sure that the leather is conditioned is one thing that you can do to help keep your shoes in tip-top shape. Canfield McNish also recommended making sure that all of your heels have non-slip pads attached to the bottom. You can buy these at shoe stores, online, at stores like Target and Walmart, or at your local cobbler. The pads help keep you avoid slipping, but they also help protect your shoes from premature wear.
You can use heat to soften the material of your new shoes. Using a blow dryer, blast your shoes with air (make sure to move the blow dryer around to evenly distribute the air and avoid melting the material). Once the material is warmed up and more pliable, gently twist and bend the shoes in the center to break them in. Don't go overboard and bend them so far that they don't return to their natural shape, or so hard that they break.

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.
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. 
Keep silica gel packets in your shoes when they’re not being worn.[3] Have you noticed after purchasing a pair of new shoes those little white packets containing tiny clear balls inside your shoe box? Those packets contain silica gel which absorb moisture and keep your shoes from shrinking. Hold on to those packets instead of throwing them away and stick them in your shoes when you’re not wearing them. You can ask a shoe store associate for extras, if necessary.
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