Learning to Walk in High Heels: Stability First

For many new crossdressers, learning to walk in high heels is one of the most important goals to meet. It can also be one of the more challenging. This guide for new crossdressers will help you succeed at that goal.

Sami’s Story

After finding shoes that actually fit, I had my share of challenges while learning to walk in high heels.

• Nearly twisting my ankle
• Nearly falling down the stairs
• Falling up the stairs
• Getting caught on the carpet
• Having a heel get stuck in a crack
• Slipping on a tile floor
• Having a heel sink into the lawn
• Having sore feet

My goal is to cut the number of problems you have while learning to walk in high heels. You want to strut your stuff successfully, not spend a week on the couch while your sprained ankle heals (no pun intended). Why not learn from my mistakes so that you make fewer yourself?

A Step-by-Step Guide to Learning to Walk in High Heels

I highly recommend that one gradually learns how to walk in high heels. My suggested approach has three key principles:

• To increase stability, gradually increase the height of the heels.
• For increasing strength, slowly increase the length of time wearing heels.
• To increase safety, master easier walking surfaces before those that are more challenging.

This article focuses on the first principle, gradually increasing stability. I explain the other principles for learning to walk in high heels in later articles.

Sami’s First High Heels

When I bought my first pair of high heels, I didn’t have anybody with whom I could seek advice. I finally decided upon some two-inch heels. Here are a couple of photos of me wearing them tonight. Considering how old they are, I think I’ve taken pretty good care of them.

The good news is that I am now quite comfortable and adept at wearing these shoes. That was not the case in the beginning!

1st Key Tenet: Stability

As a crossdresser, the last thing you probably want to do is to bring unnecessary attention to yourself. You don’t want to look like this young woman!

The most important hint I can give you is to focus most of your effort on improving your stability. The best way to learn this is to start easy and work your way up. You do this by starting with shorter, wider heels. As you become comfortable with the lower heels, move on to higher heels.

Here are three different shoes from my collection. It seems that the first one would be the easiest to learn to wear, right? That would make a lot of sense. But of course, I bought the highest heel first. I thought I had mastered my first pair well enough, so why not go from 2 to 5 inches? It isn’t that much different, right?

Such is the thinking of the overly ambitious crossdresser.

Step 1: Low Heels (1-2 inches)

For safety’s sake, I suggest that one start with lower and wider heels. If one starts this way, you’ll find that the path to mastering those really high heels becomes much shorter. Think of the short heels as being training wheels for higher heels.

As you can see in these heeled sandals, the heel is only about an inch high, and they are relatively big. Even with this shoe I still found myself trying to twist my ankle from time to time. The good news about this shoe is that it didn’t take long to master them. I was even able to walk on uneven outdoor surfaces without much trouble within a week or so. Now I can navigate with them as well as I can with sneakers.

With the heels being lower, the heel of my foot is only a little higher than my toes. This lowers the amount of stress on the calves and on the balls of the feet. In other words, I was less inclined to fall forward, which is the natural tendency when on one’s tippy toes. Most of my troubles had to do with the shoe wanting to slip off or tilt sideways. By focusing on keeping my feet level, I was quickly able to master wearing these shoes.

Step 2: Medium Heels (2-3 inches)

Once I was ready to graduate from the low heels, I went with something in the 2-3 inch range. This open-toed shoe also has an ankle strap. The strap helps prevent the shoe from slipping off my foot, giving me one less thing to worry about.

With my foot firmly attached to the shoe, I was able to practice walking on the pointed heel. Of course, the biggest challenge is having the small heel slip out from under you. Added to this is the extra strain on the ball of the foot and the calves. There is also less surface area touching the floor. This makes it more likely for the entire shoe to slide when traction isn’t good, such as on a hardwood or tile floor.

You should count on spending considerably more time working on becoming accustomed to the 2-3 inch range than the lower heels. It has been a while ago, so my recollection is a little hazy. I think it took me a month or so of wearing these a few times a week before I became comfortable wearing these.

Step 3: High Heels (4 inches)

My recommendation if you want to go up further is to limit the increase in heel height to about one inch more each time. Another thing to keep in mind is that beyond 4 inches, it is common for the entire shoe to have a platform to make the excess over 4 inches be part of a platform. So while the heel might be 5 inches high, it is more likely than not that there is a 1-inch platform, making the heel be an effective 4 inches in height. That is the case with these 4 1/2 inch shoes I am showing here. They have a half-inch platform.

When the shoes have an effective heel height over 4 inches, it starts to create a lot of problems for your foot. Most of your body weight bears down on the balls of your feet. For example, should you choose to wear 5-inch heels that don’t have a platform, I suggest you limit your walking in them to short durations. This is to avoid developing problems with your feet later.

Shoe Buying Hints

In case you were like me, starting by getting heels that are too high, don’t think that you need to rob a bank to afford to improve your stability. Focus first on getting a lower-heeled shoe that you can use solely for training. In other words, get a shoe that serves well for learning. Save the latest and more expensive styles for later, once you master your stability.

The Crossdresser Report already has a great article on shopping for shoes. Be sure to take a look at it for deciding on how to find what you need.

xoxoxo Sami

p.s., Be sure to read Part 2 of this article, Learning to Walk in High Heels: Increasing Strength.

How did you learn to walk in high heels? Leave a comment

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