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?

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.”

Trousers have been on a journey of epic proportions in the last 30 years: in the late 90s, wide and bootcut styles were common. In the 2000s, spurred by the likes of designer Hedi Slimane and the Strokes, jeans got ever slimmer. Through the 2000s and 2010s, various iterations of slim-fitting trousers became the norm until tight trousers reached the point of absurdity, as evinced by the 2019 viral photo of four Birmingham lads on a night out, their jeans so welded to their skin you could almost see the outlines of their leg tattoos.

Gradually, spurred by the fashion-forward likes of Vetements and Supreme in the mid 2010s, and then suddenly, things changed – ballooning in the exact opposite direction. Now bigger, wider styles abound. Even those Birmingham boys got on board. I hopped on the bandwagon around 2020, with some jeans from Weekday in a looser fit than anything I’d worn in the previous decade. And yet someone more style conscious than me is already charting the way back to tighter jeans.

See what I mean? If men of a certain age have always suffered something of an identity crisis when it comes to clothes, the accelerated trend cycle has made things a lot worse. It’s difficult to chart a course through these paths, which continually cross and circle back on each other at ever greater speed.

“My husband’s a similar age and says a similar thing,” Beth Pettet, head of menswear at John Lewis, tells me reassuringly. “There’s so much information out there, there’s so much imagery, there’s so much data, there’s so many points at which the consumer can access fashion in a way that they couldn’t previously that it can be overwhelming.” Plus, she thinks it’s “not so much about a pure trend being filtered down, as it was previously. The customer has greater choice, but with that, they can then struggle to navigate.”

Perhaps as a result of this wider and somewhat relentless choice, Pettet believes mainstream menswear is getting more adventurous, if in a gentle way: “There is a new mood of experimentation and discovery,” even, she says, among core John Lewis customers, who are hardly Colman Domingo. This shift has been catalysed by some traditional big name brands, be it Levi’s or Ralph Lauren, offering a bit more variety in size and shape and colour – a rubber stamp that provides a permission slip of sorts. Beyond John Lewis, the likes of the aforementioned Domingo, Andrew Scott and Daniel Craig have been taking menswear for the over-40s in creative directions on the global stage. Seth Rogen, in recent years, has given a rather unexpected template for how to dress well and with personality as a 40-plus man, offering not so much a permission slip as, perhaps, a hypothesis of that third way.

For some this will be a blessing, though I remain wary. If the choice is broader and the scope for sartorial freedom greater, so too is the possibility of getting it all wrong. Excesses of bright colours and patterns on ageing men can bring some bad associations, namely Chris Martin leaping around the stage looking like a CBeebies presenter on a stadium tour. Or the soft-cancelled Arcade Fire frontman, Win Butler, whose style has eloquently been described as “drug toddler”.

Helpfully for me, the fashion academic and writer Dal Chodha, who teaches at Central Saint Martins, is not convinced things have truly become more adventurous – granted, he’s a little more saturnine about it. He thinks that, aside from some creative industries that in theory allow more expressive dressing, most people still work in jobs that herd them into conservative modes of clothing. In general, people remain wary of standing out. “We love to believe that things have changed,” says Chodha, “but many of us are not doing anything. We’re just talking to each other [in the fashion industry] about how fab someone looks in a pair of tiny silk shorts.”

Sure, I do think Paul Mescal looks fab in tiny shorts (even if such GAA shorts bring back disappointing memories of my very average hurling and Gaelic football-playing days as a kid in Dublin circa 1992) – but that doesn’t necessarily help me. So how should I approach getting dressed as a nearly 44-year-old man? Chodha says many people gravitate to the classics. “It’s the 501 cut jean, in a very good dark denim.” This has been the route I have taken recently: after a long time bouncing around between denim brands, I landed at the safe harbour of classic 501s in black and blue, straight fit. From here on (I assure myself), it’s a straight-down-the-line, comfortable fit that suits an average bloke in his 40s. Admittedly there is a risk of looking like Top Gear-era Jeremy Clarkson, but we beat on.

Chodha continues with his capsule wardrobe list: “It’s [with] a good chore jacket that you can have some fun with colours. It looks half-smart and half-casual. It’s a good quality T-shirt, a strong pair of glasses. It’s Carhartt. These kinds of brands that are workwear. And wedded to a certain type of manliness; we can’t underestimate that. Carhartt, Levi’s, some of the sportswear brands. They’re about a certain kind of virility, testosterone.” This kind of manly workwear has, says Chodha, “become the blueprint for man dressing. And unless the high street gets braver and queerer, it will carry on like that.”

I like a chore coat as much as the next fella and I gravitate to plain white or black T-shirts; the Oxford shirt button-down staple, a reliable polo shirt. But surely I can’t just stick to clothes that could be filed under the broad spectrum of high street basics (Uniqlo, Muji), Scandinavian chain minimalism (Cos, Arket) and tasteful mid-range menswear (YMC, Folk) without feeling quite generic and identikit? I’m forever haunted by a joke in the Onion, circa 2006, which offers up a cover of “The Onion Style Magazine” accompanied by a schlubby and pale white man walking down a catwalk in blue jeans and a white T-shirt, under the headline “Heterosexual Men’s Fashion”.

Chodha agrees. “My issue with all of those brands, and largely what’s happened to the British high street, is that there’s very few kinks,” he says. There’s very few moments where something’s a little bit off, a little bit more experimental. It’s this neutralisation, this neutral palette, neutral cuts – that’s not really allowed men to express themselves. And I think that’s a real shame.”

Recently a friend told me he was looking for all his shirts in secondhand shops. Maybe more secondhand, replete with some personality, is the answer – it would certainly help my growing unease at buying new. “I only ever want to wear loose clothes from now on,” he added; the fit of secondhand is often less bodycon/muscle-tight.

I had arrived at a similar realisation: a sort of relaxed-fit, semi-casualness. Visually Stephen Malkmus is a good model: especially in recent years on Pavement comeback tours. In a straight blue jean or khaki trousers and a jacket, in all manner of polo shirts and old tennis shirts, or rolled sleeve shirts. In shorts even. He manages to carry it all off – with the same just-so insouciance that characterises his music. It helps that he is tall and lanky. Clothes tend to sit well on him.

If, like me, you don’t yet have things sussed like the Malkmuses of the world, don’t fret. “It’s an anxiety that everybody at some point has to face,” says Chodha. “I think fashion has always been a very pertinent example of a space where people feel like they are constantly not getting it right.” We’re all, ultimately, just floating in the sea, hoping for the best as we get dressed in the morning. Perhaps especially men of a certain age.