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.
If you're pounding the pavement and walking a lot in your high heels, try wearing an insert. Dr. Scholl's is well known for their shoe comfort accessories. This brand has a vast array of inserts and pads that you can purchase at almost any drug store, including some for the sole of the shoe, cushion for the ball, and even a barrier between the back of the shoe and your heel. Try the Stylish Step High Heel Relief Insoles in your favorite pair of heels for a dose of comfort.
As a New Yorker, I walk a lot. To get to and from the subway, I walk about two miles daily, if Google Maps is to be believed. Before I even got to work on Monday, the familiar pain in the balls of my feet was there. By the end of Tuesday, both feet were sore from wearing heels two days in a row. By lunch on Wednesday, I had slipped back into flats, plummeting three inches back to earth.
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.
Put your foldable flats back in your bag: A night in heels shouldn’t mean you have to hobble home. Before going out, tape your third and fourth toes together using nude or clear medical tape (the flexible kind). This helps take pressure off the ball of the foot. (A bit of biology for those who are interested: There’s a nerve right between these two toes, and the tape minimizes any strain.)

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.
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Ice Ice Baby: The key to stretching your heels to be slightly more comfortable is sitting right in your kitchen! By filling plastic bags with water, putting the bags inside your shoes, and placing the shoes in the freezer, the water will expand as it freezes and stretch out your heels. Just make sure there is no air left in the bags before you seal them tight. Seventeen suggests keeping the shoes in the freezer for 4 to 8 hours, and then "let them sit at room temperature until the ice thaws to a point where you can slip the bags out of your shoes."
Walking in heels is much less painful when the in-sole is well-cushioned. "This helps in absorbing shock in the ball area while walking and provides comfort," says footwear designer Radhika Jain over email. "These insole cushions can be made either of eva foam/latex foam or memory foam, which is the best. Nowadays you can buy them online or at a shoe store with foot-care accessories."
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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