In September I will turn 44, the supposed first iceberg of ageing. As my own personal A23a approaches, I find myself, when it comes to how to get dressed at least, not older and wiser but but more adrift than ever.
It’s not necessarily for want of effort. A while ago I tried on a pair of wide trousers: the big blocky sort that have become increasingly fashionable. I hadn’t worn anything like them before and wasn’t convinced, but was feeling bored with my own wardrobe. When I modelled them in the shop for my wife, she reacted instantly. I couldn’t pull them off, she said. You’re not an art or fashion person, was the implication. She was right; her advice tends to be sound.
As a man, when you push into your 40s it becomes harder to keep up with every new trend and perhaps there comes a point at which maybe you shouldn’t. But you might not want to totally give up either. You don’t want to seem like the old guy finally catching up with a new trend just as the last helicopter pulls out of Saigon. Equally it can be mortifying attempting to grab on to every incoming style. And so like Clinton or Blair, you scramble desperately for a sartorial third way. Or something that sits with relative comfort as the waistline expands – the middle ground. It always comes with a nagging fear that it doesn’t look quite right.
There are many greater problems in life, and yet I find myself at home, in the shop, in a changing room wondering: what the hell should I wear anymore? Perhaps this offers a way to avoid the bigger questions.
Recently a funny Instagram/TikTok sketch did the rounds. It was a parody of the genre of street interview where one gurning idiot asks another gurning idiot to rank and recommend things. Two men are desperately trying to keep up with the latest in London cool until for one of them the penny drops. “What am I doing? This is not me,” he says. “None of this is me and I just feel so tired, all the time.” He gestures at the trendy-by-numbers outfit he’s wearing, bumbag, tube socks and all. “I’m just stuck in this endless stasis of cultural peacocking. I’m a fucking mannequin for people to hang stuff on.” He lands on the crux of it: “I just feel like, what really scares me is like this idea of what’s cool is going to change again, and I’m just not going to have the energy to keep up with that.”
Many of us will have felt a piercing element of truth watching this, and there is a more mundane aspect too. Updating your wardrobe requires time, effort and money – and once you’ve done it, things may have changed again. Not to mention that growing sense that we should all be buying less and reusing more anyway.
And so I find myself, along with many men of my age, a little dazed and confused in my search for clothes that suit the time – and me.
Some of the certainties of how you dressed in your 20s and 30s start to slip away. Can I still wear Air Max or Asics? Are white trainers now the preserve of Gianni Infantino? Does a band tee still look OK? Why does that sweatshirt make me look like a teenager with grey hair? Should I wear my jeans this wide, or that narrow?
If the choice is broader and the scope for sartorial freedom greater, so too is the possibility of getting it all wrong
Trousers feel foundational to this quandary; it’s easy to make a misstep almost without realising. It feels like a style version of a line uttered in Rounders, the late 90s indie film about poker: “If you can’t spot the sucker in your first half hour at the table, then you ARE the sucker.”
