A Green Dress, Heeled Boots and the Cover of Night

This is a story about an experience I had about two years ago when I was first starting my journey into gender-non-conforming clothing. It was one of my first experiences in public in clothes that did not come from the men’s section and as such, I wasn’t nearly as confident as I am now.

The Dress

At the time, I was just starting to explore the women’s section of clothing stores and all of the possibilities within. One of my early finds was a button-down, green dress that I thought was a great combination of masculine and feminine. It looked very similar to the dress in the AI-generated image above but had a green belt with a bow instead of the black one and was more flared below the waist.

I thought it looked great on me except that the shoulders were too tight and the sleeves were too short which is a problem I have encountered with most dresses I’ve tried. Otherwise, it fit like a glove. That is ultimately the reason why I ended up giving it to my wife and only wore it a couple of times.

Leaving the House

One of those times was in public. My wife and I decided to go for a walk in the small town we live in even though it was already dark outside. That wasn’t anything unusual for us in winter since it gets dark so early here in Germany, but on that particular evening, I was feeling unusually brave and decided to just go out in the outfit I had on.

The outfit was the green dress with black tights and brown, heeled boots similar to the ones in the picture above. I won’t sugarcoat the fact that it being dark played a huge role in my decision to go out, especially at that phase in my journey.

It was cold out so I put on a black peacoat and wrapped a brown, woolen scarf around my neck. The peacoat covered most of the dress but was too short to hide the flared bottom half. Of course, it didn’t do anything to hide the tights and boots either which were fully visible the entire time.

Stepping out of the house was absolutely terrifying. I was entirely high on adrenaline and so embarrassed that I pulled my scarf up and over my lower face whenever we encountered anyone else either walking or passing by in a car.

At the time, I still had long hair and a beard, so my panicked logic was that if I hid my beard with my scarf, people might just see the long hair and not even consider that I was a man. It’s a real shame that I felt the need to hide that just to wear the clothes I had on, but it was how I felt at the time.

I can’t verify how well that strategy worked because we only encountered a few people and most were in cars, but it was a sort of “safety blanket” for me during the outing.

Out Under The Cover of Darkness

Being out in public in such a “fully femme” outfit for the first time was a rush. It felt like time went incredibly slowly, but that it was over in a heartbeat. We walked to the old city center, then through it and around the outside of the old medieval city walls.

Since it was dark, there weren’t many people out on foot, but we did encounter a few people walking. I recall a woman who was probably around 60 who watched us pretty closely from the other side of the street but didn’t say anything. She had short, purple hair, so I assume she was also into alternative fashion choices to some degree.

Other than her, nobody paid any attention to us. We walked by others who briefly looked but weren’t interested. They probably saw the combination of a dress, heeled boots and long hair, which is a familiar combination for women, and didn’t even consider that it might be a man sporting that look.

I can’t say whether the people in the cars that drove past us reacted or not because I generally couldn’t see through their dark windows, but I assume their reactions may have been similarly non-existent.

There are a couple of anecdotes from the trip worth mentioning though.


The first is that on the way home, we had to cross a busy, well-lit street. We crossed at a crosswalk where cars were required to stop for pedestrians. It was surrounded by bright street lamps which meant that we were entirely visible to the cars that had to stop for us. By that point, I had taken my scarf off which meant the occupants of the cars were treated to a well-lit view of a bearded man who was obviously in a dress and heels.

While I didn’t register any reactions, I also intentionally didn’t look. My confidence wasn’t there yet. That was the most harrowing experience of the evening since I felt the most exposed and vulnerable. It was like being in a spotlight.

Pesky Tights

The second anecdote is one that anyone who has worn tights has probably experienced: they kept sliding down. At that point, I was still new to wearing tights and had no idea that they would slide down while walking.

I hadn’t yet discovered a way to prevent that which meant I had to deal with a saggy crotch for most of the walk. I did find a few dark corners where I could not-so-gracefully pull them back up, but that only helped temporarily. It was immensely uncomfortable.

My wife thought it was funny and gave me a few tips to prevent that. I just wished she had done so before the walk.

Heels Are Terrible for Cobblestones and Mud

The last one is that I learned just how absolutely terrible heels are for cobblestones and mud. They may have been large block heels that weren’t particularly high, but I still had to step extremely carefully so that I didn’t twist my ankle. I have no idea how anyone does it with stilettos, although I’ve certainly seen it done.

I can’t recommend anyone wear them on that sort of terrain, even if they are comfortable to wear on smooth surfaces.


Throughout the entire walk, my wife acted entirely normally other than the fact that she was so amused about the problems I was having with my outfit. The tights slipping down and walking in heels on uneven, muddy ground were problems she could relate to, and she found it incredibly funny that her husband was having those problems now.

Overall, the experience was a good one I would say. It was one of the first of many positive public outings I’ve had in gender-non-conforming clothes. I’ve never worn another dress out because I don’t own many, but certainly skirts, tights and heels.

Going out under the cover of darkness helped my confidence a lot that evening. I would say I probably wouldn’t have had the courage to go out in that outfit if it hadn’t been dark. If you are still uncomfortable going out in gender-non-conforming clothes, then I would suggest you try it in the dark at first and slowly work your way up to doing it during the day. It’s a great way to build confidence.

Have you ever been out in gender-non-conforming clothing under the cover of darkness? Have you gone out at certain times of the day because you knew they were less busy or you were less likely to be seen? Let us know in the comments below!

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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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