My First Time in a Skirt & Heels in Public

Yep, you read that right. I'm writing this barely an hour after my first time out on the street as a man in a leather skirt, leggings, and ankle boots. And not during Carnival or Mardi Gras — completely seriously, on an ordinary Sunday. It was late morning, bright sunshine, spring weather, in Hamburg. Spring, because several months passed between this post and my actual "first time."

Packing up our things

It was another great short trip. Not exactly restful, but all the more eventful for it. A weekend in Hamburg was behind us — harbor tour, museum, and bar visits included.

So we slowly started packing up our things in the hotel room, tucking everything neatly into the suitcases. Our short trip wasn't just winding down — it was, for all practical purposes, already over.

This time, "that thing" hadn't been part of our plans at all. It didn't need to be, either — women's clothing had become something completely normal in our relationship, for us, for me, for her, and for both of us together. But otherwise, even when traveling alone, I usually get dressed up at least once and snap at least one photo, since the blog and social media have gained a bit more of a following by now.

My wife was still in the shower, so I ended up seizing the chance to take some photos in a completely new setting after all. It's all about variety, in the end! Readers of the blog, and every single follower on Insta or Pinterest, love it when the outfits and locations change up now and then. Of course, otherwise it'd get pretty monotonous. This time, too, a new outfit had come out of our shopping trip the evening before: a neon-green snakeskin-print mini skirt (faux leather, of course) and a lace-up crop top in black chiffon. Something I'd describe as fairly bold and special, but not exactly practical for everyday wear. For everyday wear, I'd lean more toward mini or midi skirts in a darker material, a subtle blouse, and normal boots or pumps.

Do you really always have to follow through once you've started?

There wasn't much time left before checkout, and my wife quickly reminded me to put on something comfortable for the drive. With us, time tends to get "tight" toward the end pretty often. Nobody really knows why, but it's just how it goes. Sometimes that reminder comes from me, sometimes from her. "Alright," I thought, "if she says so, let's see what actually counts as comfortable."

At first, half-joking, I picked a dark green leather skirt with pockets, wet-look leggings, and a pair of tall ankle boots in a faux-suede finish — the ones that were actually meant for this year's Carnival outfit. But since Carnival got canceled yet again, those shoes hadn't seen the (sun)light of day yet. So, dressed in exactly that outfit, I calmly packed up the last few things until even the last bag had disappeared into the suitcase — done. And there I stood, next to the bed in the middle of the hotel room, waiting for my partner to finish getting ready too.

At first, all she had to say about the outfit was a quick "well, if you dare" — then she waved me toward the door and reminded me once more that we were running out of time. The whole thrilling situation had me so worked up — and the room door clicked shut behind us.

When the cold water is really, truly cold

Looking back, there's not much about the situation I could criticize, let alone regret. Except for one thing! Why on earth hadn't I gotten myself an Apple Watch to track my heart rate and post the graph here afterward? I'm guessing my pulse was well past 100, maybe not far off from 200. My focus, though, was locked into absolute tunnel vision.

Of course, this was exactly when the room service crews had to be at their busiest. Of course, this was exactly when so many other guests happened to be checking out too. And of all times, this was exactly when the two elevators in the ten-story hotel were both in heavy use, taking what felt like an eternity. So there we stood, waiting for the elevator that would take us down to the underground garage.

From down the hallway, I heard another couple rolling their suitcases toward us, and in that exact moment I wanted nothing more than for the ground to swallow me whole. Of course, it didn't open up, any more than the elevator doors did. So we stood there, two small groups, waiting for the elevator. I could barely believe I was actually standing there in a skirt, high shoes, a blouse, and leggings, casually waiting for a hotel elevator like it was nothing.

The doors finally opened, and thanks to the pandemic (yes, it's rare to find something positive in that situation, but here we are), the maximum occupancy in the elevator was already capped at two people anyway. Finally! It felt like I had solid ground under my feet again, like I'd summited the Himalayas and finally reached the top platform. But wait — there was still the way down, the underground garage, the walk to the car, loading the car, and then back up to the elevator again, up to the room, and fetching the rest of the suitcases.

We reached the bottom floor in no time, stepped out of the elevator, and ran into yet another young couple — of course we did. Much to my surprise, though, neither of them seemed remotely interested in my outfit, and we managed to walk to the car more or less unbothered. Once there, my wife had to pull a little out of the parking spot so we could load things onto the back seat.

Of course, plenty of cars kept driving past, but I had a job to do: loading our own car. The cold water I'd jumped into was so genuinely cold that I couldn't think straight at all. Unfortunately, that also meant I couldn't really enjoy the fact that I was actually doing this, right there, right then.

Upside Down

So it was back to the elevator to grab the rest of our things from the room. Naturally, we weren't waiting alone there either, but by that point it bothered me a lot less. Still, I kept my head perfectly still, just to avoid any accidental eye contact with anyone other than my wife. We didn't run into anyone else on the way to the room, and the last suitcases were retrieved in no time.

"It wouldn't make any sense now to head down to the garage first and then back up to reception to check out the key cards," she said. "Yeah, fair point," I replied, well aware that the lobby probably wouldn't be exactly empty. "Do you dare?" she asked me, right as I was thinking, "if not now, then when?" I took a quick breath, and off we went.

And it happened exactly the way it had to. The lobby was packed, an incredibly long line was waiting to check out, and the bar was full too. Wonderful!

Everyone's always too busy with themselves

I was the best proof of that in this exact situation! I was completely absorbed in myself, and in staying absolutely cool. Sure, the faces of everyone there burned themselves into my memory — the lobby, the smell, the light breeze drifting through the hall. Of course I can still remember this defining moment vividly. But to my pleasant surprise, almost everyone there was genuinely wrapped up in their own little universe.

Sure, a small handful of heads out of that whole crowd tilted my way with a quick, furtive glance, but none of the worst-case scenarios I'd imagined actually happened. Nobody attacked me, nobody insulted me. Another lesson I can take from this: in your head, every situation gets blown up far more than it needs to be. In the end, we handed in our key cards and carried the rest of our things to the car without any trouble at all.

We then decided to park the car outside the garage, along the street, and walk through the park to find a bakery. That turned out to be the most relaxing and coolest experience of the whole day! Because it really was a liberating feeling — I was proud of my own courage, and even more proud of my wife.

A few people did pass us on the way, but again, none of the scenarios my inner worry-monster had cooked up actually played out. And believe me, I have an extremely creative worry-monster! It was only at the end of the street, looking into the bakery's shop window, that I decided I no longer had the nerve to walk through the glass door — not with roughly 20 people waiting at the counter, plus a few more sitting and eating. It's simply a different thing to walk a hundred meters toward a goal than to jump straight into the cold water, the way I did at the start of this whole experiment.

Time flew by

So we headed back toward the car, and I quickly changed into "normal" flat shoes and "normal" trousers, and took the skirt off.

I honestly can't tell you how much time passed between "alright, I'll just put it on" and "okay, taking it off again." It felt like maybe three seconds. What happened in that time felt like about two hours' worth. Realistically, it probably wasn't more than twenty or thirty minutes. But it was, without a doubt, one of the most defining experiences so far around "this whole thing."

I want to thank my wife once again here — she doesn't just put up with this whole circus, she actively supports it. And if you're a man who'd like to work up the courage to try skirts, dresses, and the rest, or a woman whose partner is doing exactly that, or has already done it, here's my wish for you: openness and trust are the key to everything in life. In relationships, hobbies, or any other (extreme) pursuits.

I'm always happy to hear from you: who are you? Do you have a husband who wears "women's clothing"? Are you a man who loves slipping into dresses, heels, and skirts? Feel free to share your own experiences with this topic. We'd love to hear them!