A Good Sole: How I Learnt To Swap Sneakers For “Grown-Up” Shoes

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A Good Sole: How I Learnt To Swap Sneakers For “Grown-Up” Shoes

Words by Mr Rob Nowill | Photography by Mr Benjamin Breading | Styling by Mr Charlie Schneider

14 March 2023

As a man in my mid-thirties, I have often felt that I belong to a kind of in-between generation, either too young or too old for everything exciting happening around me. I was too young for rave, but too old for nu-rave. Too young for Ab Fab, but too old for BoJack. Too young for the 1990s, but too old for the 1990s revival. I also believe I am simultaneously too young and too old to wear shoes.

A clarification: I do not walk around barefoot or in those terrifying, articulated socks with toe compartments that are worn by men who brew their own sun tea. What I mean is that, since my early twenties, I have hardly ever worn a pair of “proper” shoes, those with hard soles and laces. For more than a decade, I have worn sneakers to pretty much every social occasion, job interview and family event.

It is driven partly by trauma from my university years, when there was a convergence of the UK’s bizarre “no sneakers in nightclubs” edict of the early 2000s with the dying gasps of the inescapable indie scene. It meant that, for much of my twenties, the only options were pointed-toed winklepickers that could have been borrowed from a Victorian orphan or squared-off slip-ons that seemed to come exclusively in a queasy shade of light brown. They felt either hopelessly immature, in a first-job-squeaky-shoes kind of way, or like something my grandfather might have worn.

“Reviewing the footwear in front of me, I realise how much the world of shoes has diversified or, perhaps, how narrow my view of them has been”

The alternatives were so much more compelling. I moved to London and began working in fashion at 21, just as the streetwear scene was entering a boom period. Sneakers had transformed from a statement of scruffiness to an assertion of good taste. I quickly settled into a formula: New Balance or plain canvas high-tops for smarter occasions, Vans or Sambas for the pub. Compared to the sprightliness and adaptability of sneakers, leather shoes seemed lumpen, restrictive and excessively formal. And the concept of having to break them in to avoid them rubbing the backs of your heels seemed utterly absurd. They’re shoes, not a pony. Who would willingly sign up for that level of commitment?

In recent years, something has shifted. I took a job working at a sneaker magazine and saw up close how the culture around them was beginning to swallow itself. The best new releases had become almost impossible to get hold of unless you were willing to queue overnight (I was not) or fork out astronomical sums on the resale market (same). Slowly, as the era of the overdesigned, overhyped sneaker reached its peak, I found myself drawn to something plainer.

I dipped my toes in cautiously at first, with a pair of loafers by Dries Van Noten in padded black leather. They are about as relaxed a shoe as you can find without wearing slippers. They have cushioned insoles, an elasticated collar and a lighter sole that allows the wearer to pad around without the cloppy feeling of some smart shoes. They have since become a part of my regular footwear rotation. Giddy with success, I agree to try out some new styles for the MR PORTER shoot you see here, in the hope of finding more pairs that might edge out my battered-looking sneakers.

Reviewing the footwear in front of me, I realise how much the world of shoes has diversified or, perhaps, how narrow my view of them has been. Brands such as Yuketen, which offer casual shoes with a pleasing heft, have the same throw-’em-on appeal of a pair of sneakers, but look considerably more grown-up and will only look better as they become worn in (unlike sneakers, which tend to look distinctly shabby once they cross a certain scuff threshold).

The lug-soled boat shoes I borrow for the shoot are, apparently, modelled on the styles worn by US fishermen during the 1950s. It is a good era from which to draw shoe inspiration. Pragmatic and masculine, but considered in design, they will look effective in warmer weather with ribbed socks and shorts. Intrigued, I look more closely at the rest of Yuketen’s offerings. The suede chukka boots and lace-up leather styles are a solid entry point for those of us unaccustomed to heavier-duty styles.

For something a little smarter, I am cajoled into trying on a pair of suede-trimmed loafers by the shoemaker Manolo Blahnik. These are well beyond my normal sensibility. The almond-shaped toes feel more polished than anything I would normally wear. They have been cannily updated with an exaggerate sole, which grounds them and offsets any potential pranciness. They would make an ideal choice for a wedding (I have learnt the hard way that sneakers are not acceptable), but are low-key enough to wear every day, especially once they are worn in.

At this point, I am cresting on a new-found confidence in my ability to wear grown-up shoes. It only took me 35 years. It is time for the big leagues. A pair of quilted-leather lace-ups by Bottega Veneta attract a chorus of “Ooohs” from the shoot team as I put them on. If I have some initial trepidation, it is quickly dispelled. These are fantastic – comfortable, elegant and pleasingly chunky. Two separate members of the crew come over to ask how much they cost.

Am I a convert? As I write this, I am wearing a pair of decidedly beaten-looking Sambas, but I have expanded my repertoire, thanks to a pair of Gucci loafers that have rapidly become absorbed into my day-to-day rotation. And I have learnt that there is something to be said for a smarter calibre of shoe. Just invest in thick socks for those first couple of breaking-in wears. Take it from me, that is something you really cannot get around.

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