Men in Heels, Skirts and Dresses – Just a Phase?

The catwalk has known about it for a long time. Men with the right attitude have been doing it too — mostly in private, within their own four walls, but we wear it nonetheless. And now you can spot it more and more in brick-and-mortar stores. What am I talking about? Men in skirts, heels, and dresses! Yes, you read that right. But let's start from the beginning.

What's happening on the runways?

With this post I want to share something I've been noticing a lot lately. It started with a day that gave me three "aha" moments in a row. Like almost every morning, I sat down with a cup of espresso and the day's news online — in exactly that order. So there I was, at the table, swiping through one app or another on my phone. Alongside the usual politics, this time I also ended up in the "fashion" section. And I've been hoping, even dreaming, for a while now that menswear would finally embrace the pieces that are usually reserved for women. And would you look at that — once again, a major label sent men down the runway in something, let's say, unusual for the average Central European eye.

This time it was Dolce & Gabbana, who for the first time this fall showed an oversized houndstooth skirt suit on their runway. In other words, exactly the outfit I've had hanging in my own closet (in a different color) for years. You can see it on the featured image of this post: a plain skirt paired with a matching houndstooth blazer. It had me utterly transfixed, so much so that my espresso that morning was probably only enjoyable cold by the time I put my phone down.

Online retail

Genuinely inspired, I went straight into the Zalando app. Searched, opened, and was surprised. I was logged in under the main "Men" setting, which meant all the inspiration, trends, and suggestions were built around classic male outfits. That had never bothered me before, since I could always tap over into the women's categories myself and find the colors, shapes, and fabrics I was hoping for. But still, this particular app session this morning felt like something special.

Because under the heading "Outfit Inspiration," alongside the usual suits, jeans, and sweater combinations, there were suddenly entirely different outfits. But rather than tell you too much, see for yourself.

Isn't that remarkable? Skirts paired with business outfits, and revealing dresses with sporty straps — shown completely casually, right alongside gray business-casual suits and normal laid-back outfits. My deepest respect to the Zalando team! That's more or less exactly how I announced it to my wife, screenshot and all. She couldn't get on board with every outfit — the more revealing ones especially — but otherwise found it stylish, and immediately encouraged me to get active again on Instagram and here on the blog! We're going to clean things up. Not necessarily more conservative, but less revealing and even more fashion-forward combinations will be the focus over the coming months. You'll see, read, and admire it both here and on Insta.

But what does this actually mean? Is the fashion world about to completely revolutionize itself? Will the regulars at the local pub soon be wearing velvet and lace, heels and skirts? Well, I don't think it's going to be quite that simple — at least not yet. Because the day wasn't over yet, and like I said, there were three "aha" moments.

Comments on social media

Depending on which "bubble" we move in, we find more or less support for certain things. So it's no surprise that my Instagram and Pinterest are about 99% positive, with no hate or other nasty comments to speak of. Sure, there are the occasional odd requests, but they don't really bother me.

Still, in a quiet moment I found myself scrolling through TikTok. The algorithm had once again filed me firmly under "male," so my feed was full of bare skin and girls stretching artfully for the camera. The usual comments were there too — "I can't do anything either, by the way" or "finally, premium TikTok." I think you know the drill.

But one comment thread caught my attention in particular. I liked the way the video was edited, I liked the woman wearing it, and even more, I liked the dress she had on. Clearly I wasn't the only one who felt that way. Alongside the usual "where's this dress from?" questions from women, there was a male commenter asking the exact same question — and it set off a storm of replies.

The outrage ranged from "uh, bro?" to "you good, man?" to "what's going on with you?" The comment section was also seasoned with a few sympathizers, countering with things like "just let him be" or "everyone can do what they want," all the way to "maybe he just wants to wear it himself." And then, lost somewhere in the mix, was the third possibility nobody seemed to consider: "maybe he just wants to buy it for his wife?"

Why does it stir up so much reaction?

I know from experience that whenever I've worn dresses, skirts, or heels in public, I can always count on getting attention. And, just like the comments under that video, it's always split roughly three ways: amused or mocking glances, wide-eyed astonishment or outright horror, and complete indifference or a furtive glance at the very end. Admiration for the courage is one reaction. Ridicule and mockery is the other thing you simply have to put up with.

But why, really? It has absolutely nothing to do with being a stereotype. If you know how to put a look together well, tastefully, without looking cheap, it simply looks good. And why shouldn't a hemline get to brush against a man's legs? What's wrong with high heels, as long as the man wearing them can actually walk in them? Fall boots or summer pumps? If your feet and skin are well cared for, why shouldn't they be shown off — or am I wrong?

Of course, in that moment men are also projecting a lot onto their own ego. Putting someone else down gives your own ego and self-worth an enormous boost. It puts you a rung higher, automatically. But why judge at all — and especially why judge someone's appearance?

Then again, I think it's also completely normal in our society. Who hasn't seen those Facebook memes mocking a heavier woman in leggings on an escalator? She surely doesn't enjoy that kind of negative attention either. But is it really any of our business to judge?

Sure, I understand that a man in a skirt or dress isn't an everyday sight. But that's exactly why this pioneering work matters. Wear it until nobody cares anymore — because it's become normal.

A man's allowed to dream, isn't he?

But we're still a long way from that. Or are we? I mean, the type of man (and yes, woman too) who classically sneers at feminine outfits isn't really paying attention to what's happening on the couture catwalks out there. It's the fashion bubble that has, by now, made peace with pretty much everything. That crowd would never criticize you out on the street either. The critical ones are the people on the street who mouth off at anything that isn't perfectly ordinary anyway. And everyone else?

Well, everyone else mostly just stares blankly. Or whistles after you. Whether it's mocking or meant as a compliment barely matters at that point. Or they talk about you, long after you've walked past and are out of sight. They gawk. They stare, practically bug-eyed, like their eyes are about to fall out. It gets even worse in that sexually charged way of communicating that shows up during a night out — at the bar, in a club, or packed into a crowd at Carnival. Ogled, gawked at, or hit on — that's what you can expect wearing a standout outfit, one way or another.

Does that sound familiar? Are you, by any chance, a woman reading along right now? Do you love dressing eye-catchingly? Do you feel like you simply disappear when you go out in "just" jeans and a t-shirt? Can you count on every eye in the room when you're dressed to the nines on a night out?

Maybe society doesn't need to change first — maybe we need to change ourselves first. So if you want to go out in heels, skirts, or dresses: just do it. But is it fair, afterward, to get worked up about the attention it draws? Especially since you're the one who chose to stand out?

Just "doing it" anyway

And I think, by this point in my train of thought, you'll agree with me. Whenever the word "just" shows up in a sentence, it's rarely actually simple. Telling someone with a mental health struggle to "just think of something nice" doesn't work either. So why should you be able to "just" head out in a different kind of outfit? Because it really isn't all that simple to face "everyone else." And it takes an enormous amount of courage to go against the norm and do something differently, just because you want to.

But isn't that exactly what makes it exciting? I can tell you about my first time out in a skirt and heels on a public street. And looking back, I think that account lines up pretty closely with what any ordinary teenage girl would go through too. So I believe it'll only become "normal" through repetition. But I'm honestly not sure yet whether it should. Because right now, getting dressed up and slipping into heels still feels like something genuinely special to me.

So there's an important decision I still need to make within myself: do I want to keep it as something special, or should that specialness become part of everyday life?

To me, that question is far more important than worrying about the reactions that might be out there — or, quite certainly, will be. Because one thing is clear: you only get this one life. And since none of us know what tomorrow holds, you're better off starting to actually live today, and actively driving the change you wish for yourself. I hope this blog can offer a home to this movement, and to everyone who either wants to switch up their own outfits now and then, or is with a partner who does.

How do you see it? Are you fairly relaxed about all this, or do you have clear lines you won't cross? Let me know — leave a comment below this post. I'd love to hear from you.