The first time out in public in a skirt can be a harrowing experience for any man. Western society’s popular opinion that only women should wear skirts prevents a lot of men from going out in one of their favorite garments. They fear judgement or even worse, harassment.

That is why I thought it would be useful to write about my first time wearing a skirt in public. I will share what it took for me to get over the initial hurdle of leaving the house as well as my experiences while out in large crowds, trains, shops, restaurants, etc. Just for a little bit of foreshadowing: it all went extremely well!

Getting Over the Initial Hurdle

Getting over the initial hurdle of leaving the house in a skirt is by far the hardest part. The first time I went out in public in a skirt, it took group support for me to get over myself even though by that point, my wife had continuously encouraged me to finally just do it for weeks.

Despite that, it took a visit from my sister and her husband for me to finally make the leap. They had both known about my love of skirts for quite some time and so they also kept pushing me to finally wear one out in public.

One day, we took a day trip to the German city of Regensburg. My wife, my sister and her husband kept pushing me to wear a skirt and so that’s what I did. I put the gray skirt on in the image above and was a bundle of nerves all morning until we had to catch our train.

The first step outside was both terrifying and liberating at the same time. Once we had walked down the street towards the train, past our neighbors and a busy construction site, I realized that nothing was going to happen. I was outside in a skirt and I was still alive. Nobody had really paid any attention and the people that did look, didn’t look for long. They just didn’t care.

That moment was crucial for me. Before that, I was on absolute high alert as though someone was going to pounce on me at any time. Of course, that didn’t happen. Nothing at all happened. In that moment, I was able to relax some and although I was still nervous all day, I wasn’t petrified anymore and was able to thoroughly enjoy the experience.

Out and About

The experience of being out and about in a skirt for the first time was something I will never forget. My system was full of adrenaline and yet I felt a Zen-like calm. It’s hard to describe it any other way. It was at the same time terrifying and incredibly liberating. I suppose extreme sport junkies pursue a similar feeling when cliff diving or parachuting.

The train ride to Regensburg was entirely uneventful. The conductor checked our tickets and didn’t even blink an eye at the fact that I was wearing a skirt. Other passengers looked when I got on and off the train, but no one stared or even showed much interest in my attire.

Once in Regensburg, we walked around the old city center all day long. It was a warm, sunny day and the old, narrow streets were full of people. I noticed a few looks here and there, but for the most part no one even batted an eye. Walking through the city, people were busy with their own thoughts or groups or activities and just couldn’t be bothered by what I was wearing.

In the evening, we went to dinner and again, a man in a skirt didn’t bother anyone. Even when I used the men’s room, the other men didn’t react. Since I was wearing a skirt, I had to use a stall rather than the urinal, but that didn’t matter.


We were out in Regensburg all day and there were only two comments that we noticed, one of which my wife only thought she heard.

The first comment was from the owner of a small, alternative clothing store we went into. She complimented my skirt and was all smiles which made me feel wonderful. She said she thought it was great that more and more men are starting to explore alternatives to checkered shirts and shorts. Unfortunately, she didn’t have a lot of time for a longer discussion, but it was fun talking to her about the topic for a few minutes.

The second comment came out in the street while we were in a large crowd. An older couple walked by and looked at me. My wife thought she heard the woman say in a low voice to her husband: “The things young people get up to these days!” When my wife told me that, I had to laugh. Being in my mid-thirties, I’m not usually lumped in with that crowd anymore.

That was it though. Nobody stared, nobody else commented, absolutely nothing happened. The first comment made me feel justified and happy and the latter comment made me laugh. I can only repeat how much of a fantastic time it was and the reactions that I did get were fun and amusing. They enhanced rather than detracted from the experience.


Once I was outside and realized that nothing was going to happen, I began to really enjoy myself. The experience of walking outdoors with a skirt on was extremely liberating as it felt as though a part of myself that had been kept under lock and key for so long had finally been released. From that point on, the cat was out of the bag and I knew I would be doing it again.

Ever since then, I have gone out in public in a skirt more times than I can count and have always enjoyed the experience. Sometimes, I still have to get over the initial hurdle of leaving the “safety” of the house, but it has gotten easier with practice (see my post, “Feeling Trapped in a Skirt”).

I can only encourage any man interested in going out in a skirt to do the same. If it takes support from people you trust, then recruit them to encourage you and/or go out with you. Going out in a group of people that makes you feel safe can be an absolutely enormous boost to your confidence and help you with getting out in public.

Once you have made the leap of getting out the first time, it will be exponentially easier the second time and the third time and the fourth time, etc until you’ll just be able to do it without thinking much about it anymore.

What was your first time in public in a skirt like? Did you have or need help from people you trust? Tell us about it in the comments below!

The photos below show me wearing the first skirt I wore out in public, but at a later date. The outfit looked similar, but I had flat sneakers on rather than heeled boots and a black t-shirt rather than the brown one.

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About the Author

In many ways, Alex is a typical man who just so happens to enjoy wearing skirts and high heels. He is married to a wonderful, supportive wife and has a young son. His hobbies include reading, programming, metal music, playing instruments, video games, cars, hiking and a number of other smaller things.

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