Wearing a Skirt and Pumps to the Office?

Dear friends of this blog: today was the day. For the first time, I left the house alone — dressed in a blouse, blazer, and skirt — in broad daylight in my hometown, and drove to the office. Alone is worth mentioning here because my wife wasn't with me this time, though she'd sent me off with wonderful compliments. And I can honestly say — at least going by the feedback from my colleagues — it simply looked good.

Have Courage and Just Do It

So much for all those great, ultimately useless phrases telling you to just go for it… My experience is that whenever the word just shows up in a sentence, everything about it is true — except that it's ever actually simple.

The same goes for the small matter of simply leaving your apartment — walking out in a skirt, blazer, and blouse, past the elevator, down to the parking garage.

And once you get in the car, start the engine, find the exit… wait for the gate to open, and leave the territory that felt safe until now, you know things are getting real.

But honestly, I'm making this sound far more dramatic in writing than it actually turned out to be (or was).

The Second First Time

My wife and I had already been out on the street in heels and a skirt about nine months earlier. Back then it felt sheltered and anonymous, in a city known for its fables and its tolerance for unusual tastes: Hamburg.

Nobody knew us there, and it was the first "ride" in that kind of outfit.

Now, many months later, I went to work in a similar outfit. It wasn't some long-planned expedition or anything like that. I can't even claim I agonized over it for weeks, building up anticipation. It simply happened.

I had the blouse, the blazer, and the skirt on just for fun around the house, got an overwhelming compliment, and then the question: so, are you actually leaving the house like that now? I said yes. And I went.

The Second Day

Why am I not dwelling much on the first day? Simple — because all I got was compliments, and I did it again the very next day.

So, again showered in compliments, I left the apartment and drove to work.

It was sunny, with noticeably better weather than the day before. Which meant more people were out on the street too.

It already felt unusually normal to me. Because it simply looked good, and I'd always liked dressing sharply anyway — until now, that had meant: suit, chinos, or a shirt.

Now my wearable wardrobe has expanded many times over. Gone are the days of shame and holding back. What's arrived are the days of outfit variety.

Which absolutely doesn't mean I have to — or want to — do it every single day. Not at all. To me, it simply means my range of options for getting dressed has grown considerably.

I Don't Dare — How Do I Get Started?

If you're asking yourself this question, there's really only one answer: just do it. And you'll read that word plenty more times in this post — but don't force it, and above all, don't force it on anyone else.

I know the comparison is a bit of a stretch, but imagine a good friend suddenly goes vegan. That's not immediately a problem for you, right? You see the vegan meals, sure, but nobody's forcing you to eat them yourself. And you (hopefully) wouldn't make snide remarks about it, let alone start bullying them over it. So the two of you simply coexist peacefully, side by side.

But if that same friend starts trying to convert you, restricting what you're allowed to grill because meat might "contaminate" the vegetables or cheese — even with a separate grill tray — then that starts limiting your own choices and probably gets on your nerves pretty fast. And if the whole thing escalates into a barrage of "ugh, I could never eat that" or "how can anyone even enjoy that stuff," then your patience is probably running thin.

Even though veganism absolutely has its place, this example is meant to illustrate something. You can bring up your clothing style carefully, work it into a relaxed conversation, and mention that you'd like to try wearing a skirt or heels — or both — and gauge whether anyone would actually be bothered by that.

Start the conversation with something seemingly trivial, and try to see things from the other person's perspective — a good manners guide helps enormously here too (book recommendation: Anstand und Ellenbogen: Wie Sie zu dem Menschen werden, dem Sie selbst gern begegnen möchten*) in building a smooth, considerate way of coexisting with the people around you. So if you want to take your counterpart's point of view into account, ease them into the topic. Sure, you could also jump straight in — full outfit, makeup, and wig, clacking into the office. But then you have to expect some genuinely startled looks. That's just how it is.

Talk, for instance, about your stance on gender topics, or on queer and LGBTQ issues. That's a great way to illustrate that in a free country, everyone gets to do and wear whatever they like — and that all you're asking for in return is to be left in peace, without having to sit through anyone trying to convert you. Everyone can wear whatever they want. You don't have to personally like it, but you'll tolerate it, as long as nobody crosses your own personal line. It's hard to imagine anyone disagreeing with that framing. And once you've got that far, you can casually mention that you'd like to come to the office in a skirt sometime too. Be prepared for reactions like "sure, just do it" or an amused "haha, yeah right." And then — you just do it!

Who's going to say no to that at that point? By the way, you'll also find psychologically grounded, well-researched perspectives and fresh angles on this whole topic in my book, Help, My Husband Wears Women's Clothing.

What Others Think About It

I'll put it this way. Whether I'll need to revise this post and this section down the road, I honestly don't know.

But my thoughts on the topic right now are clear.

If you're not bothering anyone, not forcing anything on anyone, and not trying to convert people — then the worst you can expect is a few looks or some extra attention. And that just comes with the territory.

So the reactions so far have been anything but negative — quite the opposite. Everyone who's seen it immediately admires the courage and compliments the outfit choice. I've even gotten the usual "where's that skirt from?" or "wow, where's that blazer from?" questions — from women.

I think I'll report back in a few weeks or months on how life has developed, and how this new way of presenting myself has settled in.

Personally, I'm still entirely the same person. I've just finally started standing behind myself, my clothing style, and who I am.

I also believe that, for everyone out there, it's simply a matter of the timing being right. You can't force it at all. It either comes — or it doesn't.

What do you think about all this? I'd genuinely love to hear your thoughts. Whether you're a woman with a partner who shares this inclination. Or whether you'd simply like to start your own outfit revolution in everyday life. Though I'm hesitant to even call it a revolution these days, given what I see on the catwalks and in online shops… but that's a topic for a separate post here on the blog.