3 Tips for Learning How to Walk in Heels

I sat at a coffee shop tucked into a cobblestoned corner in the colorful port city of Valaparaiso, Chile, characterized by kaleidoscopic street art that drenches its steep, rolling hills. Cross-legged, sipping a cacao hot chocolate, I kicked off my Birkenstocks that’ve blistered the balls of my feet. Window watching passers by, I was fixated on one woman donning chunky-heeled booties climbing a ladder with spray paint. It’s not the mural before her that blew my mind; it’s that, lest you missed it, she was balancing on a ladder on a cobblestone hill in high heels.

And my Birks — designed for comfort (certainly not style) — were killing me.

I’m no stranger to high heels. I’ve got about as many high heels at home as Carrie Bradshaw has sweaters in her oven. Some call me a hoarder; I call me a collector.

But the difference between the woman on the other side of this windowpane and I is she appears to be a natural-born expert, and I’m a learned professional.

Is it hard to walk in stilettos? Yes. Is there a trick to walking in high heels? If there were a trick, we’d all be using it. The fact of the matter is that some women just seem to strut seamlessly. For others, like me and perhaps you, walking in heels can put you in pain without practice.

Learning how to walk in heels is not necessarily an easy feat. But with these three simple steps, you can master the art of what’s essentially a balancing act. 

I can’t promise that you’ll be performing at the level of this woman outside, but I can guarantee that you’ll feel a lot more comfortable.

Your first order of business is to find yourself a pair of high heels that actually fit your feet comfortably.

For example, if you have wide feet, pointed-toe shoes are not your friend; they’re a friend of your dreaded adversary (the bunion). Likewise, if you have high arches, you don’t want a pair of high heels that don’t offer any give on impact (they’re super flat on the balls of your feet, instead of boasting at least a little platform). Typically, heels that are too tall or that don’t offer any ankle support are also going to be substantially more unbearable than heels of a reasonable height with an ankle strap of sorts. And, usually, a chunky box heel is going to feel a lot more supportive than a pencil heel.

I’ve worn horrible high heels for so many years that, when I find a pair that don’t make me want to cry, I buy them in every color. In fact, I’ve narrowed down my everyday shoe collection to almost strictly Steve Madden. I know his shoes fit me well, they offer supportive straps and a chunkier heel that’s not too tall, and the materials don’t rip up my ankles or dig into my toes.

When you go shoe shopping for high heels, don’t only consider how the heels look and how they might feel if you’re going to be walking a while, but also consider what they feel like when your feet are simply strapped in and your standing put. If they hurt already, don’t even entertain the thought of them.

Having to break in shoes is the worst part of buying new shoes (well, it’s arguably the only unpleasant part of buying new shoes, beyond what the purchase might do to your bank account). 

Before you take your new high heels out anywhere you’d be bound to them for a while, practice breaking them in somewhere less committal. For example, don’t wear them to the office straight away, when you know you’ll have to sport them for at least eight hours and where you may be on your feet all day. Instead, wear them to a coffee date with a friend, when you know that you’ll only have to walk to and from the cafe, and you can head home afterward if the heels are really crushing your sole (pun intended).

You can even break your heels in at home, by wearing them around the house for a day. The point is to stretch the shoes so that they fit your feet more precisely and to scuff the bottom of the shoes to give you better traction.

Whenever you’re breaking in new high heels, it may be wise to put Band-Aids on any places that the shoes might rub, such as your ankles. This is because, the material of your unbroken-in shoes is still tough and they can, therefore, more easily induce blisters. Preventative Band-Aids can help you bypass that part of the process altogether.

The key to walking in high heels, which truthfully shouldn’t hurt that badly if you pick a pair that fit and break them in, is to wear them with confidence. You’ll stand up straighter and walk with more conviction if the high heels on your feet look good — because, when they look good, they’ll feel even better.

Listen, looking good is entirely subjective. If you don’t do dresses, don’t do a dress. If you’re a ripped-boyfriend-jeans and oversized-sweater kind of woman, go for it. Whatever you decide, make sure that, when you’re wearing what might otherwise be uncomfortable contraptions on your feet, at least make sure that you feel good about your decision to do it. And you may feel better about it if it’s because they seriously complement your killer outfit.

What’s more: You can purchase hidden helpers that’ll allow you to walk with more ease and, thus, confidence. If you do have a bunion that’s suffocating in your high heels, consider a toe separator. If you do have high arches that feel like they’re tearing apart in your high heels, consider arch support pads. If you have an ingrown toenail that’s getting crushed inside your high heel, consider some padding for it.