Why I Wear Skirts and Heels, or Why Showing Your Feminine Side Makes You More of a Man

In recent years, there has been a noticeable feminization of men’s fashion. Men in both skirts and heeled shoes not only make a regular appearance on fashion runways around the world, but more and more male celebrities have started to wear skirts and heels in the limelight. While the trend hasn’t yet made it to the streets in most places, the community of men who have started wearing clothing typically associated with women has grown.

This is particularly noticeable online. Men donning dresses, skirts, stilettos, etc have started to appear and trend in large numbers on social media. This doesn’t just include young men either. The ages range from teenager all the way up to grandfather. Beyond social media, the number of forums and online communities focused on this phenomenon has also grown – some of which are linked here.

So what is driving men to do this? Any man you ask will give you an entirely different set of reasons for his motivation which makes it very difficult to pinpoint why this trend is taking off at the moment. While I can’t entirely speak for other men, I can talk about my personal reasons — several of which I probably share with other men out there.

How I Started Wearing Skirts and Heels

Before we get into why I wear them, let me give you a bit of background information about how I started wearing them.

My interest in clothing typically associated with women first began with high heels. I am the type of person that likes to experience things for myself which means I got curious about what it would be like to wear them and there was only one way to satisfy my curiosity: try it out myself.

As such, I found a pair of heeled boots in my size (US size 13; not an easy task), ordered them and wore them at home when my wife wasn’t there. It took a while before I was able to muster the courage to show my wife (who was exceedingly supportive), but I’ll write about that topic another time.

I found that I loved wearing them. They gave me a thrill of doing something forbidden and yet nothing actually “bad”. My curiosity was officially piqued and it wasn’t long until I ordered my first skirt to go with the boots. Again, I wore it at home, alone without the knowledge of my wife until I was able to muster up the courage to wear it in front of her. She was, again, very supportive and welcomed me challenging gender norms.

From them on, my obsession grew – and “obsession” is what it has become to an extent. I probably own more pairs of heels of various types than men’s shoes combined throughout my entire life. My skirt collection has also far exceeded any of the number of men’s clothes I have. 

I don’t generally wear dresses (although I have a few!) because I find they don’t look very good on me. They are cut for the female body and with my broad chest and square, masculine shoulders, they look strange on me in my opinion. So I tend to wear skirts with a male shirt of some sort.

Why I Wear Feminine Clothing

Now that you know how I came to wear skirts and heels, I will talk a little bit about why. I wanted to give some background information on how I got started first because I wanted to emphasize that I didn’t actually have a reason other than simple curiosity. That was more than a good enough reason to get started!

Anymore, I wear skirts and heels almost every day which is made possible by being able to work at home full time and by my wife’s support. By wearing them so often, they have become more meaningful for me. They have, to an extent, become part of my identity and how I express myself.

I am a firm believer that every man has a feminine side, but that most men repress it. Most boys learn not to show it when they are bullied at school, by older siblings, or even their own fathers. “You throw like a girl!” or even just plain “Don’t be a girl!” are some of the worst playground insults that a young boy can be forced to endure and teaches them that having a feminine side is a bad thing.

Through my experience of wearing traditionally feminine clothes, I have learned that there is absolutely nothing wrong with a man expressing his feminine side. In fact, I would argue that it makes you even more of a man, but I’ll get to that more below.

I started wearing feminine clothes out of simple curiosity, but now wear them because I have learned to proudly embrace this side of myself. For me, it is a bold statement of rejection of what the bullies tried to pound into me and other boys when growing up. It is also a statement of confidence that I am happy with and proud of who I am and that I won’t let others’ judgements restrict me anymore.

That, at least, is the more philosophical reason for why I love wearing them. There is also a much more pragmatic reason: comfort. Skirts are insanely comfortable! A man who hasn’t tried wearing one is really missing out. They are cooler in the summer and, combined with the right tights or leggings, can be warmer in the winter. 

And, of course, we can’t forget that being able to twirl in a skirt is a reason all by itself to regularly wear them!

Why Wearing Feminine Clothing Makes You More of a Man

It may seem counterintuitive to say that wearing feminine clothing makes you more of a man, but there are a plethora of reasons as to why it does.

First of all, it means you are more in touch with yourself as a person. If you are not afraid of your feminine side, it makes you a more well-rounded person because you are letting part of yourself out of its cage. People are complicated and multifaceted, but society has taught us to hide certain aspects of ourselves because they are not socially acceptable. Many men fear their feminine side because, as I stated above, they have been conditioned to be that way by others who are not comfortable with their own feminine sides.

Another reason it makes you more of a man is because you dare to do it! You dare to fly in the face of others and explore what society still deems abnormal. If we are talking about what society says is typically masculine or feminine, then daring to not care what others think and forging your own path is a distinctly “masculine” trait. While I don’t entirely subscribe to that point of view, it is certainly something that is commonly referred to as typically male: a real man does what he wants, when he wants to and doesn’t care what others think.

We also can’t forget to mention that a real man cares about his appearance. It would be difficult to attract a partner, secure a business deal or do any of those typically “masculine” things by dressing sloppily. Wearing skirts, dresses, heels, etc opens up brand new possibilities to enhance your wardrobe as men’s fashion is generally pretty limited and monotone. By incorporating typically feminine clothing into your style, you can add more variety to your appearance which will give you a fresh look that others won’t have. This is exactly what the runways from Paris to New York are trying to accomplish right now and can really give you an edge and make you stand out.

Conclusion

There are tons of reasons for wearing what is typically considered feminine clothing as a man. Your reasons may be different from mine and that is perfectly fine. They should be. The clothes we wear are a deeply personal thing and everyone should have their own reason for wearing what they choose to wear.

Going against the grain isn’t easy, but is certainly rewarding. Anyone who has made an impact on this world has fallen out of line in one way or the other and has gone against what was expected of him or her. Even if wearing clothes that people aren’t used to seeing on men only makes an impact in your local neighborhood or group of friends, you have still made an impact and challenged people’s perspectives – and that is something that should definitely be applauded.

Did I miss any reasons for why wearing feminine clothing makes you more of a man? Would you like to share any of the reasons you wear feminine clothing? Feel free to in the comments below!