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.
Reactions
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.
Conclusion
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.
Alex, thanks for sharing. I can’t recall the first time I went out beskirted, as it’s been some years now. I don’t recall the initial fear you note (just curiousity), but I do recall the thrill and sense of freedom. And as you note, few if any comments or notice.
I suppose if we had chosen longer, flowy, floral chiffon styles, we might have gotten more response, but a simple, monotone knee-length skirt is just not that in-your-face, really. I still prefer my denim skirts for daily wear (sometimes a tunic or shirtdress works, too). I don’t think I’d be comfy out in a satin mini, but more for practical limitations than risk of disdain.
I drove my sports car to a Cars & Coffee meetup this morning, wearing a seersucker shirt and dark blue denim 20-inch skirt with sandals. That was a first. Goodwife wondered if that crowd (with lots of muscle cars in the mix) would be unwelcoming, but I had no issues. I walked the whole field several times. Spoke with many of the other car guys there. I might have half-noticed a look or two from the sideline chair-sitters, but nothing even remotely hostile or negative. I doubt I’ll ever prefer two-legged duds over the single-opening types for most times and purposes. Cool, breezy, and a sharper, cleaner look than wrinkly-crotched shorts on a Summer day. Hooray for menskirts!
Sounds like a great experience! I would have also been a little concerned about that particular crowd, but I’m really glad to hear that no one was bothered by it. The more people are exposed to it, the more they will accept it as normal!
One question though: you mentioned needing a stall rather then a urinal in the men’s room. Why? I find it easier at a urinal in skirt than in pants. Front of hem up, front of undies down and away we go. Much easier than the zipper, then hunting blindly for undies under shirttails and working the goods out through it all. Have you become comfortable with urinal use since that first outing, and just recall in that first time here? If not, may I recommend it? Yet another win for men’s skirts, actually.
I’ve never actually tried to use a urinal in a skirt. Most of the time when I go out, I wear skirts that are more pencil-like in nature, so pulling up the front hem isn’t really possible since they’re too tight. I have to lift the entire skirt. I do use a urinal when I wear a kilt though.
Hmmm, Maybe it’s a length thing rather than a pencil-vs -line thing? I usually wear 22 inch skirts that hit just above my knees. The pull-up is an easy reach then. If you prefer longer wear, I can see how that might be more of a barrier to convenient urinal use!
Mine also hit just above the knee, but they tend to be quite tight which means I can’t just pull up once side. I could see it working in one of the a-line skirts I have though.
I have found the same, that nobody really cares. I started wearing my skirts around my apartment for about a month before I got brave enough even to walk to the mailbox. Well we, my GF and I were going for a hike in the mountains on a trail that wasn’t travailed much. I was wearing my shorts but brought a fleece mini skirt. About a half a mile into the hike I switch into the skirt. We did come across a few people hiking and a couple people on 4 wheelers and not even a look, nobody cared. We finished the hike and stopped for dinner and fill up with fuel for the way home. Again nobody cared or even looked. That gave me the confidantes to wear a skirt in my home town. So I started to wear it when my GF and I would go for walks after she got off work. Again when we met people nobody said anything. With the new found confidence I started buying more skirts and wearing them more often. Well now they are all I wear, except when I am on my motorcycle, and I now have over 50 skirts and a few dresses. They are great ho hike and backpack in, the extra air flow is great and bathroom stops are quicker. I only wish I would have started wearing skirts sooner. But I guess at least I am wearing them now.
That is a great story! It really just goes to show that you have to just get out and do it! The more you wear skirts outside, the more confidence you’ll build. At some point, it will become as easy as going out in jeans or shorts.
Thanks for sharing your story, it’s really inspiring. I’m not that lucky to have anyone “close enough” who would support me in wearing skirts (not having any girlfriend, ever, and my brothers telling me I look awful in skirt, ‘like a pervert’). I try to understand them, as they must find it difficult to figure out, why 28-years-old guy suddenly starts wearing skirts. I do wear skirts during ‘home office’ as I’m basically the only guard of home during ‘working hours’, but once I see 3 PM – well, ‘goodbye’ to the skirt and bringing trousers back. My neighbour has seen me outside in a skirt and thigh highs (but let’s say I arranged it in a way to make it happen) – she said that she’s totally good with it and the combination I picked looks really cool.
So after multi-thinking about this and seeing footage of people like you going outside in a skirt (well, probably easier to do it in Germany than in Poland0, I found some atoms of courage inside and take my dog for a ca. 20 minutes walk in the morning, in a black “circular” skirt (I guess, I’m still far away from being familiar with all of these types). As the neighbourhood is rather calm and definitely not a ‘city core’ type of place, I encountered max 10 guys during such walk. Like in your story, people seemed to not really care although looked at me for as long as I was in their ‘vision area’ – I tried to not pay too much attention to it, but man, it’s difficult really to just go straight and keep head up, and ignore everything else. You really must develop a mental for that way of ‘being’. Or maybe they cared but just didn’t speak it loud enough to make it hearable? I wish I don’t think about that. Not sure, but I believe I’ll give it a go to continue doing this hopefully on a daily basis and maybe, maybe find some courage in the future to go to a public place like this. Still, having someone to support you (at least for the first few times) just by walking together must be extremely helpful. You can at least spend time on talking rather than thinking about the situation that should be really ‘normal’ for everyone.
You’re welcome! I’m really glad you find it inspiring! I think a lot of people have a hard time wrapping their minds around why people “suddenly” want to break out of the gender norms they’ve been following their whole lives. I put “suddenly” in quotation marks because most of the time, it’s sudden to them, but not to the person doing it. They then struggle to accept the change and merge it with the person they thought they knew. I’m really glad you worked up the courage to go out with your dog in a skirt! You have to start small. That’s where I started because it’s the only way to work up the courage to go out in a busy district. At some point, it will become so normal that you will decide to take the next step and do it in a crowded area. Even that will become normal for you at some point.
To quote, “I’m really glad you worked up the courage to go out with your dog in a skirt! You have to start small”.
I know it’s an oldish post now but that word order made me chuckle: The beskirted chihuahua, perhaps?
In brief, my first outing in a skirt was little short of disastrous. I had bought one in a chain store in England not known for being avant-garde, to say the least, choosing it solely on its black colour and right size. I then wore it to a presentation night for pub quizzers, being held in a pub (where else). Clientele was mainly male. No comments of any sort except a jokey one from a female I knew. To my chagrin I then ‘discovered’ that the skirt was pocketless – something I should’ve checked in the store – so that I had to carry my wallet and phone (having no jacket, as it was a warm night). Embarrassing. Moreover, the skirt was too long, being slightly below my knees, a pull-up one, so no belt loops, and had too much material anyway, of a style called “ponte”.
I wore the skirt once more in a semi-public space and then got rid of it. Moral of the story: don’t rush into buying your first skirt out of enthusiasm, check it out thoroughly if you can. I did learn from that mistake.
That is a good point! The word order is a little strange! I have seen dogs in tutus though. 😉
You’re absolutely right about not rushing into buying your first skirt! It sounds like you had a very interesting experience to say the least! But at least it was embarrassing only because of the skirt not having pockets and not fitting well rather than because of what another person did or said. In that sense, I would say it was much more successful than you give it credit for!
I have a few skirts without pockets that I love for how they feel and look, but I always miss pockets. You really can’t underestimate them!
The thin edge of the wedge is not for me. Yesterday I went to four museums in Fort Worth wearing a full gold metallic pleated skirt with a black ruffled square dance petticoat, black shirt with a gold foil tiger symbol. Entering the Modern Art Museum several girls employed there gave some nice vibes. Bra? Absolutely not, female impersonation is not my thing. Part of what has afflicted menswear for centuries is this nagging idea that men must be plain and drab. That comes from old English puritanism, European sumptuary laws reserving fancy garments to nobility, the awful French Revolution which equated fancy clothes on men with political repression, the Industrial Revolution which also had men in dark colors (so stains wouldn’t show), and the London boozer Beau Brummel who invented the modern business suit. Men need not limit themselves to plain and drab skirts. There are metallic fabrics, pleats, polka dots, ric-rak etc. See Kathakali in India and Tanoura in Egypt. See link.
It’s really great that you go out in brightly colored skirts and petticoats in Texas! I certainly agree that menswear is very drab and boring and it’s interesting to hear about the origins of that. It certainly makes a lot of sense. Thanks for sharing!
Hello, I am also a skirt wearer. When I first started wearing them in public, it was SO scary. I was stunned that it was not very different than going out in my other clothes. In the early days, men in womenswear was a lot less accepted/seen/talked about. People would stare, giggle, and point me out to their friends. Now, 15 years later in 2023, people will look down and then go on about their business. No giggles these days. Also, I normally don’t see any sign that people tell their friends to “look at the dude in the skirt.” I blog about my experiences at http//joeypress.wordpress.com
I’m happy I found your site!
Joey
At the start of civilization, who was wearing a skirt/dress was about one thing only—someone not riding a horse. Pants were invented by Mongols and Parthians for riding horses. That is how men got stuck with a twin tube leg garment, which religious zealots and psychiatrists force on men. Psychiatry condemned women in pants until there were so many women in pants they became a majority and psychiatry is only witch hunting against minority elements. In 1942-1945, 18 million USA women wore pants in war factories, at the insistence of factory managers, who concluded pants make a better industrial work garment. No war factory work in 42-45 would have meant “no women in pants today.” Social forces not gender cause clothing behavior, but unrestrained freedom of choice should be the sole determinant of apparel choice. A skirt is a leg garment—anyone with legs should be free to wear any kind of leg garment! Luke 7 proves that Deut 22:5 does NOT ban skirts on men!
Pants for riding horses makes a lot of sense. Pants certainly have their practical uses, but so do skirts. And I absolutely agree that freedom of choice should be the sole determinant of apparel choice. Thanks for sharing!
Thanks for sharing and the encouragement! Though I haven’t made the full fledged leap to public skirts, I do have a election I wear at home with my spouses support. For the public side I have adopted a wide variety of kilts – gets me the freedom and comfort I so enjoy, without perceived condemnation. There are some men who have expressed their displeasure with my attire, but when I point out how much women enjoy the fashion statement, including their wives, they pretty well shut up. Also given my position in business and community the kilts are acceptable and a conversation starter. Also a bit challenging for me as I don’t have an athletic body to show off… yet, so again the kilts are an acceptable alternative. Had all the same anxiety/anticipations/observations you expressed and it IS exciting. I look forward to the day skirts become more commonplace for men- perhaps if there were specific designs… also like the concept/simplicity of dresses but again effective designs would be helpful.
Keep up the awesome work and overall encouragement! Thank you for doing so!!!!
You’re very welcome! I enjoy writing articles on this blog and sharing my experiences.
Kilts are amazing for exactly that purpose. It’s how I started gaining confidence in wearing skirts outside since, as you mentioned, there isn’t the perceived condemnation. I am also looking forward to the day when skirts become more commonplace for men, although then the thrill of doing something socially abnormal will disappear as well. That may be a good thing for most people though. 🙂