10/09/2026
WHY DOES GETTING DRESSED GET HARDER AFTER 40?
I’ve noticed something rather odd about the men who come to see me in their forties and fifties, because you’d imagine that getting dressed would have become easier by this point in our lives, wouldn’t you?
You’ve probably got more money to spend than you did at 25, you know yourself considerably better, you’ve stopped worrying quite so much about what everybody else thinks and, if we’re being completely truthful, you’ve probably got enough clothes already to survive a small apocalypse.
And yet I keep meeting men who tell me exactly the opposite.
“I don’t know where to shop anymore.”
“Nothing seems to fit me properly.”
“I’ve got a wardrobe full of clothes and nothing I actually want to wear.”
Or the one I hear perhaps more than anything else: “I just need to sort myself out.”
And I’ve been wondering whether the problem isn’t that we’ve somehow forgotten how to dress at all.
I think it’s that everything around us changed while we were busy getting on with our lives.
Swipe through, because I suspect some of this may sound rather familiar.
SWIPE 👉
Think about how much easier work clothes used to be.
I’m not saying they were necessarily better, but if you worked in a certain sort of job you more or less knew what was expected of you. Suit, shirt, proper shoes, perhaps a tie and off you went.
Now we’ve got “business casual”, “smart casual”, “dress for your day” and whatever else somebody in HR has come up with, which all sounds wonderfully liberating until you’re standing in front of the wardrobe at 7am wondering whether you’re about to arrive looking like the Chairman or the bloke who’s come to fix the Wi-Fi.
SWIPE 👉
And actually, I don’t want to dress like that all the time either.
This is probably much closer to how you’ll find me when I’m having dinner with friends. White T-shirt, jeans, trainers and some sort of casual jacket, because getting older doesn’t mean you suddenly have to spend the rest of your life in a blazer and proper shoes.
But there is a difference between dressing casually because you’ve chosen to and slowly