What does it feel like to wear heels as a man?

Not all men who wear gender-non-conforming clothing such as skirts or dresses wear heels. Some will gladly spruce up their outfit with a pair of heels while others aren’t interested due to the well-known physical drawbacks. Both are legitimate as everyone has their reasons for their decision, but I happen to be one of those that enjoys a good pair of heels.

Last May, I wrote a post called “What does it feel like to wear a skirt as a man?” which has become one of my most popular articles. As such, I thought it might be interesting to write about what it feels like to wear heels as a man since I am just as passionate about them as I am about skirts. As with the previous post, most of what follows is gathered from my own personal experience, however, I will draw on some of the discussions I’ve had with other men who regularly wear heels.

My primary focus here will be on what I would consider heels of a fairly normal height: something in the range of 1″ (2.5 cm) to 6″ (15 cm). Extreme heels that are higher than that are an entirely different beast with an entirely different set of skills needed to wear and walk in them.

While this post focuses on wearing heels as a man, the physical feelings of wearing heels isn’t restricted to just men as anyone of any gender will experience it physically in much the same way. I will get into the emotional side of things with a stronger focus on men a little later.

Physical Feelings

Unlike wearing skirts or dresses, wearing heels is physically demanding. It takes practice, coordination and determination to be able to wear them regularly which means, as we have seen above, they aren’t for everyone. When you wear heels, you are essentially walking around on the balls of your feet much like you do when you walk on tiptoes, albeit with better support. The heels and soles of the shoes provide support which makes that posture tenable for longer periods of time. A good pair of heels will support your entire arched foot so that your feet won’t fatigue as quickly as in a cheap pair of heels without as much support.

One aspect that both expensive and cheap heels have in common, though, is that you have to get used to the change of balance. There are multiple, unfamiliar directions from which gravity is pulling on you. To begin with, your center of gravity is shifted slightly forward and onto the balls of your feet which means you are forced to counterbalance the change by pulling your shoulders back pushing your chest forward. Exactly this change in posture is what makes some people so attracted to women (or men) in heels.

You also have to contend with rebalancing your weight with the muscles in your ankles and calves in new ways. After all, you don’t want to twist an ankle or just simply fall over. How much you have to do that will depend on the size of the heel in terms of both height and width, but I will get into more detail about that a bit later.

One of the last, and perhaps most harmless, physical changes is the change in your height. This is, of course, much more noticeable the higher the heel you have on. In my case, I am 6′ 2″ (188 cm) without heels which means if I wear some of my taller heels, I have to watch my head when walking through doors. It’s harmless until you bump your head a few too many times.

Interestingly enough, this is the part my wife likes the least about me wearing heels. I tower over her without any shoes on, but when I wear heels, it feels like my head is in an entirely different weather climate from hers.

Comfort

My use of the word “comfortable” above when describing heels might make some people chuckle or even roll their eyes, but if you do get the right pair, they can be surprisingly comfy. Despite that, I still wouldn’t compare them to a good pair of flat shoes in terms of comfort, but if you get the right pair, they aren’t the torture devices so many people believe them to be. This negative image comes from women frequently complaining about them and, when you look at some of the pairs they wear, it’s no wonder. They are frequently of the wrong style to provide enough support for their feet which fatigues them and makes them sore.

When wearing heels, I’ve found that the level of comfort is directly correlated to two primary factors: the existence of a padded plateau and the width of the toe box. In my experience, the plateau only needs to be a couple of centimeters high with some padding on the insole for the ball of your foot to make an enormous difference. In this case, my use of the word “plateau” is a bit ambiguous because a thick sole is enough, but I will continue to use the word for consistency.

If I wear heels without a plateau, my feet do get sore after only a short while, but I can wear heels with one all day without an issue. Well, that is, if the toe box is wide enough.

Over the course of the past decade and a half, I’ve had dozens of pairs of high heeled shoes and one thing I’ve realized is that my feet start hurting rather quickly in shoes with pointed or heavily tapered toe boxes. These force your toes to be squeezed together into a wedge shape that, after a short while, makes them ache. The lateral pressure coming from the tapered point combined with the vertical pressure from putting most of your weight on the balls of your feet leads to some very sore feet.

The next time you step on your tiptoes in bare feet, pay attention to how your toes move. You will see that their natural tendency is to spread out to distribute the weight better. When wearing heels, it’s similar to walking on your tiptoes which means your toes need to be able to spread out. Pointed toe boxes don’t allow this which means only a relatively small section of the balls of your feet is bearing the brunt of your weight.

By choosing heels with a toe box large enough to allow your toes to spread out more naturally, you will have better weight distribution and won’t experience nearly as much pain, if any at all.

You can see an example of what I mean in the image at the top of the post. Those are my favorite pair of heels that I own and while the toe box is slightly wedge-shaped, the tapering doesn’t really set in until it’s past my toes. The boots’ plateaus are also only about 3/4″ or 2 cm in height, but still provide more than enough padding that my feet don’t get sore.

This is in strict contrast to the pointy-toed, plateau-less pumps you see a lot of women wearing and complaining about it. While some people may enjoy wearing them because of how they look, I dislike them because I can’t stand to wear them for longer than a couple of hours.

Another misconception is about the height of the heel itself playing the primary role in how comfortable the shoes are. I would argue that, as long as we’re not talking about extreme heels (6″ or 15 cm and higher without considering the additional height of the plateau), it doesn’t matter very much as long as the toe box is wide enough and you have enough padding for the balls of your feet.

There is also the question of the width of the heels themselves: stilettos versus block heels. I think this is a matter of practice, training and terrain. Block heels obviously have the advantage that they are wider and therefore provide a studier base for your weight. This is certainly more convenient and, frankly, in most cases, more comfortable than having to keep your balance on thinner heels like stilettos.

However, I’ve found that wearing even high stilettos for long periods of time can be just as comfortable as wearing block heels of the same height as long as I am mostly indoors where the terrain isn’t uneven, rough or unpredictable. Wearing stilettos outside is an entirely different experience. Besides the risk of twisting an ankle, it can also be exhausting. Stilettos require training and patience to be able to wear for long amounts of time as they require the muscles in your feet, ankles and legs to do a lot more work keeping you balanced. Through consistent wearing of stilettos, though, I’ve trained these muscles so that I hardly notice a difference between them and block heels when indoors.

Emotional Sensations

When I first started wearing heels it was out of curiosity. I wanted to experience the physical sensations because I had watched women wear them and had always wondered what it would feel like. However, I quickly grew attached to them despite the fact that they were physically less comfortable than my flat shoes. Like skirts, they symbolized freedom from gender stereotypes and I always thought they made an outfit, whether otherwise gender-conforming or not, really pop in a way that flats couldn’t compete with.

In the end, most of us who regularly choose to wear heels, no matter the gender, would probably say the emotional aspect is the primary reason we wear them. I would imagine most men who wear heels wear them for similar reasons as for women: completing an outfit, height, or just because they like them. However, for men, it has the additional aspect of being taboo. Wearing heels as a man is a form of rebellion against society’s restrictions on what men should wear or how they should behave — something that could also be said about wearing skirts or any other type of gender-non-conforming clothing.

However, unlike skirts or dresses, wearing heels comes with its very own, instantly recognizable soundtrack: clicking on hard surfaces. If someone is walking on a hard surface in heels, you don’t even need to glance at them to know what kind of footwear they have on. This naturally draws attention to the wearer which can be both frightening and empowering.

Some women I’ve talked to about it have said that the sound makes them feel more confident and in charge. That is especially true in a classic business context which is still mostly dominated by men. It seems silly that a simple noise can have that effect, but it signals to the observer that, “I’m here and I’m not afraid to be noticed.” It’s the specific mindset that it takes to wear them in front of others, even for women, that provides a confidence boost.

That noise, however, can be terrifying for men who are taking their first baby steps (pun intended) in them in front of others. Since it draws attention to them, it means that people are much more likely notice. While some men wearing them relish that attention (much like the women), it is a real turn-off for those who aren’t confident wearing them in public yet.

The good news is that not all heels make the sound. In fact, none of the heels I wear out in public click on hard surfaces as they have large, blocky heels made out of hard rubber with rubber soles. The reason for that is no longer fear in my case, but rather the fact that those heels are much more practical to wear on uneven, unpredictable ground. Anyone who has ever tried to wear stilettos on cobblestones will understand what I mean. Plus, the sound honestly drives me nuts after a while. I rather enjoy the sound at home in short bursts since I don’t walk as much, but when I leave the house, I tend to be on my feet for the most part and prefer the silence.

However, I do have to admit that it used to be fear that drove me to originally seek out quiet heels. Much like when wearing a skirt in public for the first time, the first few times I ventured out in heeled shoes were terrifying. I was afraid of being judged and of the comments I was convinced I would get. However, like with the skirts, no one has ever said anything except to compliment me. I have even worn my heeled boots to work on multiple occasions.

Other than at work, where I did get a couple of positive comments and questions about them (I posted about it here), no one has ever said anything about them. It’s liberating to be rebellious and wear what I want in public. I would even call the feeling of freedom addictive. It is about self-expression and feeling good with your appearance — whether others approve of it or not.

Conclusion

As much as I love wearing heels, I don’t wear them all the time, even if it might seem that way from my posts and pictures. At most, I might put them on once or twice a week, sometimes even less. It isn’t because I don’t want to wear them, but rather because I want to ensure I’m not doing any physical damage to myself. We all know that extended use of heels can be detrimental to your physiology even if it’s good for your psychology. I’ve found I enjoy wearing heels more when I wear them in moderation.

Understandably, they also aren’t everyone’s cup of tea and that is just fine. The best part about clothing is that you can choose what you put on your body. I enjoy wearing them both at home and occasionally out in public, but I don’t actually wear them outside very often because I find them too impractical even with the block heels. However, the temptation is sometimes too strong to resist.

Not everyone is going to have the same experiences, physical or emotional, that I’ve had, but what I’ve garnered from conversations I’ve had with others is that there are still a lot of commonalities. I would say “especially amongst men”, but interestingly enough, that isn’t the case. The men I’ve talked to who confidently go out in heels experience them in a very similar way to women who wear them out in public: people either shake their heads or they are impressed by the confidence it takes to wear such footwear.