I often wonder how I’ll dress as an old man. Will it be immaculate M&S slacks, nice mid-gauge sweaters and charmingly large brown shoes? Perhaps I’ll go all intellectual and deck myself out in tattered tweed and soft collar shirts. Seemingly all “creative” men (actors, playwrights, designers etc.) of advanced years have collectively agreed that the only suitable garment is an unlined cotton blazer, well-worn with the tell-tale shine at the elbows. Good for hosting panel discussions, trips to the Barbican, visits to the Brompton bicycle store etc. I might even end up as one of those curiously buff old men with a manicured grey beard, Peaky Blinders hair and amorphously tattooed hands.

Regardless of clothing, it’s clear I won't be wearing trainers. In the same way that young people don’t watch Midsummer Murders, old people don’t wear trainers. They just don't. Not proper ones, anyway. (If you can buy them in Holland & Barrett, they’re not trainers.) It’s mad because you’d think after a life on your feet, you’d want to give them a rest; take the pressure off that ever-creakier hip. But no, apparently there comes a point in every person’s life when they say, “OK, that’s enough of comfort, I want leather and laces. Until I die.”

madrid, spain   march 11 zinedine zidane, addresses the media after being announced as new real madrid head coach at estadio santiago bernabeu on march 11, 2019 in madrid, spain photo by quality sport imagesgetty images
DIEGO GONZALEZ SOUTO//Getty Images

In truth, I fear that time may have already come. Last year, I bought a pair of New Balance 990s in the classic pale grey colourway, and try as I might, I’ve barely worn them. They are an undeniably excellent shoe, and when I see pictures of people wearing them, I think, “oh look, a cool shoe that it isn't tragic for people in their thirties to wear, I must dig mine out.” But when I put them on, I look like a teenager attending his first school disco. Like the rich kid in movies that has all the cool stuff but none of the cool itself.

I’m insecure about my Casablanca New Balance, too. And my Kiko Kostadinov Asics… even my Raf Stan Smiths leer up at me from the ground, two pleather orbs of shame. I bought a pair of Stepney Workers Club daps (daps?) in the hope that their simple black and white palette wouldn’t be too infantilising, but infantilised I was. (Perhaps I should have looked at the new campaign, which is literally just children at play.)

The fact that I called them “trainers” should be proof enough that my time as a gladiator in the sneaker coliseum is coming to an end. I used the word “slacks” earlier, too, so clearly the 16-24 zeitgeist has long since left my wheelhouse.

It’s just that it seems to be a choice between too much shoe, or not enough. The 990s are too big (which may have something to do with my exorbitant shoe size), whereas my Vans Era are too modest. Not enough heel, not enough oomph. White tennis shoes have gone the way of the overshirt, which is to say, they are reliably inoffensive but devoid of any tangible style, whereas everything else makes too much of a statement. I like the idea of cosplay in menswear – it’s why I often wear a ripstop gilet that hype kids would refer to as “tactical” – but perhaps the novelty of clothes stops at the heels. Your shoes don’t lie, and if a 32-year-old Londoner is wearing 22-year-old climber’s shoes, it’s obvious. And it stinks to high heck.

Thankfully, there has never been a better time to not be a trainer. Right now, all the vibes (all of them) are emanating from loafers. Be that leopard print at Alyx, two-tone at GH Bass or square-toe at Martine Rose. But there’s momentum behind cowboy boots, too. And Cuban heels. And slides and strappy bondage sandals and slippers.

instagramView full post on Instagram

You can wear any or all of the above with any or all of the clothes you have in your wardrobe. We’ve reached an especially eclectic epoch of menswear; one wear the irreverent and vaguely competitive nature of “fit” culture means that men (and people in general) are fusing sartorial elements that were previously assumed to be diametrically opposed. Look at ASAP Nast in Tabis and a DJ. Look at Tyler in DMS and a deerstalker. Look at Justin Bieber.

I might be blowing things out of proportion. Perhaps I’m just blaming all my ageing angst on my feet, and really trainers are still good. It’s just their filling that’s the problem. I’m going to mull it over while slowly hoarding pebblegrain oxfords and shaggy suede boat shoes. That seems like a sane way to prep for old age.

Like this article? Sign up to our newsletter to get more articles like this delivered straight to your inbox

SIGN UP

Need some positivity right now? Subscribe to Esquire now for a hit of style, fitness, culture and advice from the experts

SUBSCRIBE