The Button-Down Shirt Disaster of 2025

Time got away from me a little, as it conveniently tends to do when a doctor’s appointment looms. I threw on a shirt with a button-down collar – first mistake right there. The button was refusing to button, which it should’ve thought about before becoming a button.

I should’ve gone with a T-shirt, but I was already in deep – every other button done except for the last couple of holdouts up top.

Normally, this is when I’d call in the cavalry (my wife), but she was at work, leaving me to tackle this mind-twisting, dexterity-sapping puzzle solo. Either this condition I have is worsening, or the price of button holes has gone up like everything else, so they’re making them smaller.

Sure, I could have just left the collar buttons undone. But when I spot that oversight in the wild on others of my species, I smugly congratulate myself for having my act so thoroughly together. I wasn’t about to forfeit that moral victory.

So I dug deep, mustered what mojo I could summon up, and crammed that button into the fabric. I wasn’t stopping – even if it meant boldly forcing a new hole where there was none before.

Finally – success. Glorious, silent, entirely uncelebrated success.

I raced to my appointment, where I received exactly zero compliments on my buttoning triumph. Although, I did catch the receptionist glancing once or twice in my collar’s direction. The doctor, too, I believe, subtly admired my work. No need to worry, cavalry – I got this sussed. And if anyone needs a keynote address on the fine art of buttoning, I’m available.

Later, back home, I went to change and happened to pass a mirror. I stopped.

Something was… off.

I leaned in closer to examine the general vicinity of my neck. Dear reader, I cannot recall exactly what I saw. Buttons misaligned with their counterpart, even mixing up collar buttons with rank-and-file buttons. Weeks later, when the trauma subsided, I tried to recreate it for this post, but couldn’t do justice to the horror I saw on that day. I’m posting a feeble approximation here cleaned up for those who may get squeamish, but just imagine it twice as horrific.

I guess I need a course or two here.

The Fine Whine

So, to all of you navigating Act III, here’s what I’ve learned from this trip to humility land:

Sometimes the day doesn’t go the way we planned. Sometimes the shirt wins. But grace lives in the trying – especially when we’re trying alone, trying clumsily, trying anyway.

Button-down shirts are tricky. Life is trickier. Be kind to yourself. Laugh when you can. And if you’ve got a cavalry, thank them. If you are the cavalry, take a bow.

And remember: there is no age limit on learning something the hard way.

Now, if you’ll excuse me, I’ve got a doctor’s appointment coming up Monday I need to start getting ready for. This time, I’m bringing the cavalry.

6 Comments The Button-Down Shirt Disaster of 2025

  1. Michele Hermansen

    You may be retiring from your place of employment, but please do not retire from writing!

  2. Paige

    I always tell my kids they can pull off any look if they wear it with confidence, which it sounds like you did! But also, maybe fashion makes fools of us all.

    1. Eugene Dennis

      What a good way to look at it. I think what I pulled off was more in the “wear it with bold ignorance” approach, but – baby steps.

Comments are closed.