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

Most men have never had the pleasure of wearing a skirt, but many are curious about what it feels like. Some cautiously try it with kilts while others are simply too afraid to cross that imaginary gender line. This post is for those who want to know what it feels like but have never worn one. It will be a combination of what it feels like physically as well as emotionally. Both will be somewhat subjective since we’re talking about feelings, but I will do my best to describe them based on my own experiences as well as what I’ve heard from other men.

For me, the first word that comes to mind when I think about this topic is “liberating.” Whether it is physical in the sense of having more freedom of movement or airflow, or emotionally in the sense of breaking out of the box society has put men in, the word “liberating” is a great way to describe it.

Physical Feelings

There is nothing quite like the feeling of putting on a loose skirt. Imagine not having to wear anything at all — in terms of freedom of movement, it is very much like that, and yet you remain decently covered. There is a reason so many men immediately start twirling once they put on a skirt for the first time. You are not restricted by the legs or the tight crotch of the pants or shorts and thus can move your legs without restriction. There just simply isn’t anything there to get in your way. Of course, we all know that with that freedom comes responsibility in public as you have to pay attention not to flash anyone.

All of that does, of course, assume you are wearing a loose skirt. Wearing a tight pencil skirt won’t give you this type of freedom of movement, and if that is something you are going for, you might want to avoid tight skirts. That said, tight skirts are restrictive in an entirely different way than jeans or pants. They squeeze your legs together from the outside, and if they are tight enough, will stretch every time you take a step. That stretching means there is some degree of resistance with every step you take and every move you make. I happen to love that feeling because it constantly reminds me I’m wearing a skirt, but that is highly subjective and others will find it irritating. To me, it feels almost like the skirt is hugging my legs.

One thing both types of skirts have in common, however, is the increased airflow. This is particularly valuable in the summer when it is hot. I’ve found that even the tightest skirts I have are cooler to wear than any of the shorts I have. Combined with cotton underwear, you can feel the cool breeze on a hot, summer day in ways you never thought possible, and it feels absolutely amazing. Of course, loose skirts are breezier than tight skirts, but even the tight skirts are better than anything with an inseam.

It’s not always warm enough to go out with just a skirt, though. Sometimes you need tights, leggings or something similar to keep yourself warm. That is where some of the advantages of wearing skirts listed above become moot. Suddenly, you are not only wearing a skirt, but also a bifurcated garment underneath with the same restrictions as any other garment with an inseam. Some people solve this issue with long, crotch-length socks, but others are happy to wear tights since they find them either physically more comfortable than, say, jeans, or they enjoy it on an emotional level.

Emotional Sensations

When I don a skirt, I feel like I can truly be myself. It might sound strange, but it gives me a sort of “license to be free” that I otherwise don’t feel like I have. It’s entirely in my head, but I believe it comes from the sensation of breaking out of the mold that society has imposed upon me as a man. I feel more connected to my true self.

As such, I don’t mind wearing tights or leggings during colder weather because, although some of the physical freedom is no longer there, I still feel emotionally liberated. That is also the reason I love wearing tight pencil skirts: physically restricting, yet emotionally liberating.

There is also the confidence boost that comes with this. When I feel like I can be myself, I feel confident and proud. If the outfit with the skirt looks particularly good, then I feel doubly confident — even more so than if I like the outfit I’m wearing with clothes solely from the men’s department.

This feeling of confidence and emotional freedom is also the reason why I like wearing high heels despite the fact that they have a well-deserved reputation for not being the most comfortable footwear. But that’s beyond the scope of this post, although I do intend to write a similar one about how it feels to wear high heels as a man.

Conclusion

Skirts, and even dresses, are not only physically freeing in that they give you much more freedom of movement and increased airflow, but they can also be emotionally liberating. Either way, you can only benefit.

If you are on the fence about trying a skirt, I can highly recommend you do in whatever form you feel most comfortable with. For example, start with a kilt. They are a type of skirt that is considered acceptable for men to wear, even by the most staunch conservatives, but will still allow you to experience the liberation of your lower half for yourself.

What a person wears can have a profound impact on who they are. That is why they say to “dress for the position you want and not the position you’re in.” Dressing well always gives you a confidence boost, and incorporating some clothes from the women’s department can push it even further, making your style unique, memorable and stand out in the best of ways.