Blazer and Skirt at the Hotel Bar

I'm writing this post from a completely unfamiliar city. From a hotel, with a small but pleasant bar.
It's not too busy — it's Monday evening, a time when cities generally aren't too busy anyway.
And I'm starting this post from my hotel room. I'm wearing black leggings, a pair of black heeled ankle boots, and a great business outfit.
I already got compliments on the blazer and the blouse, which is now encouraging me to go all in.

And here I am. I've already tried plenty of "should I or shouldn't I" generators online — all of them, incidentally, delivering the same verdict: you should…

And honestly, I don't quite know why I'm making such a big deal out of this. Because it's "really" just an outfit. Just that. And I've already worn it to the office, driven around in the car in it, and plenty more. And yet I'd still like to take you along for what it sometimes still means to me, slipping into certain clothes.

But before I lose myself entirely in writing this post, let me say this for the moment: out of the hotel room, into the elevator, and down to the hotel bar — in heels, skirt, blouse, and blazer. Why? Because I'm already wearing it anyway.

Other People's Stares

If I'm being honest, the biggest worry is entirely in your own head. Nobody's going to judge you — you'll get looked at, sure, but that's hardly surprising, I'd think.

And you're not exactly unnoticeable either, when you're wearing boots that click on the floor with every step 😉…

But now, on to the moral of the story.

The bartender told me an inspiring story. Most people go through their everyday lives shaped by "you just don't do that" and "what if everyone did that." They're consumed by judgment. By envious looks. And sometimes even contempt. But why? Because, really, they're the ones not actually living their lives. He went on to tell me that he can read bitterness and every missed chance in people's eyes. Their looks are steeped in "if only I had." But there's one thing none of them had: the courage to change. And the "just do it" gene.

And what's left for us, in the end? We only get the one life. This one chance. This one moment.

And no matter how you want to dress: when exactly do you want to do it? Later? In retirement? In your next life? And which one would that even be?

Every decision is the right one, as long as you can live with the consequences. Doing something is just as valid as not doing it. It's your life!

And as long as you're not preaching, not stepping on anyone's toes, or being a nuisance, just do whatever you want to do.

In the end, you'll get judged and evaluated far less often than you think.

Coffee on Your Shirt

Obvious things stand out. That's clear. If you spill coffee down your shirt right before a business presentation and then stand in front of an audience, everyone will see the stain. Everyone will think, "oh, someone had coffee trouble this morning." A few might think, "that bothers me so much, can't they just change their shirt?" And even fewer will think, "I find the person wearing that repulsive." And on top of that, it matters what you make of it.

If you handle it with humor, with confidence, the stain stops mattering pretty quickly.

And if you carry yourself with confidence, as if it's the most normal thing in the world — because to you, it is — nothing bad will happen to you either.

Of course, there are certain occasions where you're bound by a dress code. And that's a good thing too. Funerals, or similar occasions, come with certain expectations, out of respect alone. Or at weddings, you shouldn't try to compete with the bride, if you know what I mean.

In every other situation or setting, wear it like it's the most natural thing in the world. The initial looks pass. And once the first bit of culture shock is over, that's when the fun actually starts. Trust me.

The Rest of the Evening

I have to admit, somehow everything turned out differently than I'd pictured in my head. I'd imagined the worst-case scenarios. In the lobby sat a woman who looked like she belonged on a reality show, styled to the nines. At the front desk stood the hotel's female staff, currently helping a male guest. But who knows whether any of them even looked up as I walked past him. And once I was past, I honestly didn't care either way.

And do you know Murphy's Law? I sat alone at the bar, until I decided to head back and change into a different outfit. And of course, it happened exactly the way it had to.

Right at that moment, a lot of people decided they wanted a drink at that very bar. Of course they did, right? But for most of the time, nobody cared in the slightest.

And then even more people arrived. There I sat. Business travelers, private celebrations, singles and couples. Do you think a single one of them so much as batted an eye?

Would I Do It Again?

The question doesn't even need asking. It was a wonderful evening, full of genuine connection and interest. And that kind of interest is perfectly fine.

But here's one piece of advice I'll give you: stay yourself, relax, and "just do it."

And if you've been following this blog for a while, you already know that any sentence with "just" in it is anything but simple.

What do you think about all this? What are your own experiences? Do you have a man in your life who does something similar? Are you the man who wears it — or wishes he did? I'd genuinely love to hear from you!

With that.