As those of you who follow me on Instagram have probably already seen, I wore a skirt to the office for the very first time last week on October 23, 2024. The photos in this post show the outfit I wore that day and were taken back at the hotel afterward. I work remotely because the office is about 200 km (about 125 miles) away from where I live which means I am rarely there.
I have written about wearing heeled boots to the office before, but I had never actually worn a skirt which is significantly less subtle. Given that I might visit the office twice a year, I don’t have a lot of opportunity and when I’ve been there, I haven’t felt entirely comfortable with wearing a skirt because I don’t know the people very well. Everyone I work with on a daily basis also works remotely, so most of the regular office-dwellers are unfamiliar faces to me.
This time was different though. While I still didn’t really know anyone, I was there to attend a training seminar for software architecture which meant I got to know the group I was with fairly well after only a couple of days. By Wednesday, I decided I was comfortable enough to break out my gray denim skirt and black cotton leggings as you can see from the pictures above and below.
It goes without saying that I was incredibly nervous despite all of my experience wearing skirts out in public since this was a situation that involved my employer and coworkers rather than random people on the street. Leaving my hotel room, I headed down to the breakfast room which is where I ran into a couple of the other attendees of the seminar who also work remotely. I got my breakfast, sat down and chatted with them while eating. Not a single word was mentioned about my choice of dress which helped me relax about the situation.
We then drove over to the office building together. Walking inside, we hiked up the stairs to the fifth floor where the office is. Even though some of the group was behind me and most certainly couldn’t have missed the fact that I was wearing a skirt, no one said a word and absolutely nothing changed in our interactions whatsoever.
Once in the office, we headed for the conference room where the seminar was taking place. The teacher was there and so was the rest of the group. People looked at me and the others as we entered the room but in exactly the same way they would have if I had been wearing jeans or slacks.
It won’t come as a surprise to most of you who have read about my experiences wearing skirts in public that not a single person mentioned my skirt or treated me any differently throughout the entire day. It was exactly the same as though I had been wearing bottoms you would find in the men’s department.
The only odd looks I got were from a couple of older ladies at the restaurant where we went to eat for lunch. They were very openly staring at me and whispering to each other which is the sort of scenario that rather amuses me since they had probably never seen a man wear a skirt before.
After a long day at the office, I drove back to the hotel with my coworkers and we went our separate ways for a couple of hours until we decided to meet up for dinner. I stayed in my skirt and we had a great meal at a Vietnamese restaurant that we walked to on a major road. Again, absolutely nothing happened.
My skirt wasn’t brought up even once. They never looked at me strangely, never treated me any differently and were just as friendly and professional as before. In fact, they were much more interested in the fact that I was American which seems to fascinate a lot of Germans since I speak German fairly well.
All in all, the experience was exactly as I had thought it would be: entirely anticlimactic. No one cares what you wear as long as it is context-appropriate. For better or worse, I still probably wouldn’t wear a skirt when visiting one of my company’s customers since it may, unfortunately, still have an indirect impact on my company, but I will absolutely wear a skirt again when I visit the office in the future.
What an amazingly positive experience for you. I’ve yet to wear a skirt in public, even though I am a daily kilt wearer, but your experience is very encouraging.
Thank you! It really was a great experience and I hope to repeat it next time I need to go into the office! I can only recommend giving it a shot! It’s not a whole lot different to wearing a kilt. 🙂
Great post and perfect experience. Sorry I fat fingered the rating. I thought it was going to open to a rating pop-up.
Thank you!
Look at all the water bursting from that broken dam! I foresee an even more skirted future for yourself. Seems you’ve hurdled the last big hurdle in your life and can now be unabashedly yourself! Congratulations!!!
Love the way you made everything work. This is truly an outfit that says I am male, am not starting a transition and am confident. You were also remarkably comfortable I bet.
It’s amazing how much relief one feels with these events that’s are actually non-events. I actually had a similar-ish event when I wore a kilt in front of my sister and mother when I was at a local park hiking and they met me. Was nervous as a whore in church but said it’s time to just be me. Few comments, none bad and I hiked a glorious day in front of many. Also wore a kilt in my childhood hometown. Also remarkable for only positive comments. The feeling of relief I had was overwhelmingly healthy. Can’t post a picture here but if you go to https://forums.delphiforums.com/mensskirts/messages/1/151
you can see it.
Love that you are pushing the envelope so well and helping the rest of us out as you become mentally better as well.
Thank you! I’m really happy to have finally done it. It feels so liberating! Once I got over the nervousness, I was very comfortable. I feel that skirts are generally more comfortable than pants but when you are nervous, you are hyper-aware of what you’re wearing which makes the skirt feel tight for me. That is especially true for one that isn’t an a-line skirt.
Congrats on the kilt experience! That’s the perfect first step!
That was about the same experience I had the first time I wore a skirt to work. Most of my co-workers had seen some posts of me in a skirt on FB & IG but I hadn’t worn one to work. I started to wear a skirt back and forth and changing in my truck and wore shorts into work. Well one day I just said the hell with it and wore it into work. Nobody said anything, but I did change into my work clothes quickly. After about a week I realized that nobody cares and that was when I started to wear my skirts all the time, except when I’m on my motorcycle for obvious reasons, safety first. Just 2 weeks age I had a “Black Tie” event to go to in N.Y. My HS X-C coach was being inducted into the H.S. sports hall of fame. I thought that would be perfect for my long black skirt, lavender shirt black tie, of course, and black suit jacket. It was a hit, no one said anything negative, and two complements from a couple women. I really enjoy the comfort and freedom of wearing skirts. I also like being different and being myself unfiltered. My girl friend supports me 100% and was pushing me in the beginning when I said that I wanted to try wearing a skirt. 10 years ago I would have bet the ranch that there was no way that I would ever ware a skirt or dress, but we get wiser as we get older and care less what other people think. I’m glad that it went well for you, although I don’t see why it wouldn’t. I think times are changing and most people are becoming more excepting. So I say “skirt on and enjoy fun clothes”
It sounds like you eased into wearing skirts at work which is definitely the easiset way to overcome nervousness or concern. It also helps others slowly get used to seeing you in a skirt rather than you just suddenly showing up in one. Most people are kind and professional enough not to say anything even if they don’t necessarily understand it or agree with it as long as it is workplace-appropriate.
That’s great that you wore a skirt to the ceremony and even got copmlements! Your girlfriend also sounds wonderful and supporting. Times are definitely changing for the better in that regard!
Wonderful story – thank you for sharing. It helps to destigmatize men in skirts. Recently I was visiting a friend who told me, “garments don’t have genders.” There you go! So far, I’ve only worn skirts to work-related social functions after office hours. I haven’t worn a skirt during regular work hours except when there’s a social occasion. I hope to do so one of these days.
Thank you! I’m glad you enjoyed it! Destigmatizing men in skirts is the primary goal of this blog and I really hope that it makes a difference, even if it’s small.
Congrats on wearing skirts to work-related social functions! That is also something that takes a lot of courage to do up front.
Oh, you wore shorts without an inseam. Nice look. For the most part office clothing is neutral and men’s clothing doesn’t show skin. Nice look that fits in.
Yeah, that’s pretty much what they are. It’s perfect for a more conservative environment like the office.
“shorts without an inseam” I love it. If anyone ever asks me if I’m wearing a skirt (it just doesn’t seem to happen though I am, almost daily), I shall definitely have that phrase at the ready, “Oh, you mean these shorts without an inseam?” HA!
But as I have said almost as often as Alex, and likely experienced even more often, It’s OK. Dress well and appropriately, and be happy: you will be accepted and respected, end of story.
Today, I drove several hundred miles, stopping at multiple service areas (and pee stops – I’m not that young anymore). I wore a teal shirt with western yoke and pearl snaps over a tan A-line mini and open sandals. It looked (and felt) quite good, if I say so myself. Nothing more than an occasional smile or glance at any of those pump, food, or restroom stops; some of which would not even be considered ‘progressive’ places. Let’s hope that November brings redemption for progress here in the USA and not a backslide into authoritarian conformity.
It is a great phrase! Experience definitely shows that no one cares if you present yourself as confident (even if you’re panicking inside) and dress well. You may even get compliments which is something very unlikely to happen when wearing standard clothes from the men’s department!