How To Wear Sneakers With Tailoring

A marriage made in heaven or one destined for the divorce courts? The Rake weighs in on the sneaker and suit trend.

The suit, forever the paragon of sartorial style, has never really gone under the knife since it was first popularised in the early 19th century. Sure, a little nip and tuck here and there, but by and large, the suit has remained unchanged for nearly two centuries, not least for the simple reason that it flatters the male physique when constructed correctly. The accessories one wears to complement the lounge suit is a different matter entirely. British dandy Beau Brummell was, for example, largely responsible for the world’s adoption of the necktie, which he sported in favour of the cravat.

Today, we find ourselves in the midst of yet another sartorial paradigm shift, one in which sneakers are muscling in to replace classic shoe styles such as Oxfords, Derbys and monk straps as the bookends to a tailored ensemble. Sacrilege or evolution? Well, perhaps a little dose of both, but here atTheRakewe feel like there’s room enough in this town for the two of them. Sneakers have become such an indelible part of our lives (the sneaker resale market alone is worth $1 billion), that to restrict them to purely casualwear does seem like a missed opportunity. Of course, there are both occasions and professions for which only a fine pair of polished Oxfords will suffice, but you cannot deny the metronomic march of casualwear in today’s menswear market. As such, sneakers have snuck in from the leftfield as a genuine dress-down alternative, and whether you approve or not, there is a certain rakishness to ripping up the rule book from time to time. So with that said, we’ve located a panoply of gentlemen who have deftly carried off this once unholy matrimony between the suit and sneakers, all in very different ways, but each with aplomb.

Sat together, the gentlemen below make clear that ‘tailoring’ is a more diverse category of menswear than one is often led to believe. The gentleman on the left is sporting some classic separates; a reasonably smart ensemble that works well with his choice of burgundy tassel loafers. His friend, on the other hand, has opted for an ironically iconic pair of New Balance, otherwise known as ‘dad sneakers.’ A contentious choice no matter what the outfit, but we can see this gentleman’s logic: the cropped khaki chinos with a slightly crumpled linen-blend blazer and denim shirt convey a sense of considered insouciance, which is further accentuated by the dull grey sneakers.


March 2022


Also read