Shoes like Jagger — how to wear trainers as a middle-aged man

When Mick Jagger married Bianca Macías in 1971 wearing trainers with his Tommy Nutter suit, he made a real statement. High and low culture did not often mix promiscuously half a century ago. Of course, they hardly mix in 2021: we dress down all the time now, and high style survives only at the margins. Trainers are ubiquitous in every context and among every age group. We live in a world of sneakers. Every other shoe plays a supporting role.

That this presents a test for older men is obvious from the fact that so many of us fail it. Would-be Jaggers with an awkward pair of designer sneaks poking out from beneath suit trousers are to be found at every party. Often it looks like a sad stab at youth by someone who would do better to go for middle-aged gravitas.

But the right pair of trainers looks great. As with everything, it’s about choosing carefully. So start with a little taxonomy.

First of all, while there is such a thing as a truly classic sneaker, it is a smaller category than generally thought. I saw my father, who was born in the early 1920s, wear what he would have called “tennis shoes” only two or three times in my life. They were white canvas, with fine wavy serrations in the blue rubber soles. Sperry, probably. One can buy a close equivalent today (£75, sperry.co.uk). Sure, they look aggressively preppy but, worn with shorts, they are a lot better than the dreaded docksider or boat shoe.

Next classic: the Converse All Star. Cheap, versatile, casual but (in off-white canvas) somehow mature. In black, still slightly punk rock. Despite many efforts, though, you can’t wear them with a suit or proper trousers, as they just are not substantial enough. They get lost under the cuffs. Their close cousins, Jack Purcells, with a slightly thicker sole and heavier profile, fare a little better here. A nice new pair, in summer, with a light-coloured suit? Sure.

The next, much larger category are Generation X nostalgia sneakers. They are the sneakers my generation love because we wore them growing up. Adidas cap toes, Sambas and Stan Smiths; canvas Vans, with laces and without; Puma classic suedes; Nike Air Jordans, Air Forces and Waffle trainers. The throwback trend has made all of these easy to buy again. The strategy here is simple: wear the ones you wore as a kid, and be happy.

Another important group are what I would call new classics, which were not around in the 1980s but feature old-school styling. Nike Blazers go here, as do Onitsuka Tigers. A slightly more obscure Japanese brand, Moonstars, are my own favourites (in purple). They are a relative of Converse All Stars but they are higher quality, with better detailing. If you can find a pair, buy them.

While I love wearing sneakers that echo the ones I wore as a kid, I choose much stronger colours than I did as a self-conscious seventh-grader. Indeed, outside of canvas classics, I think there is a general rule here. With trainers, subtlety is to be avoided. If you are going to wear a definitionally casual, comfortable shoe in a context that requires some style or formality, the only way to do it is to go for it — all the more so if you are opting for a high-low outfit/shoes combo. Sneakers ought to shout.

Which brings us to a category that is absolutely to be avoided: “nice” or semi-formal sneakers that, in their desperation, the brands and department stores that once sold men proper shoes now push on us. In white, black or brown glossy leather, they try pathetically to simulate “real shoes” and often have price tags to match. The whole thing is sad. Even less expensive normcore sneakers depress me. The move towards dressing down was meant to be fun.

The big, clunky, foam-soled New Balance 990s, in blue, are admittedly a genre in their own right — the king of all dad shoes. They are a big “go to hell” to the whole idea of fashion, and maybe there is something to be said for that. Again, though, I don’t see the fun.

And fun is the point, which is why if a grown man isn’t going to go with a totally classic sneaker, then it’s the weirder the better. Try some Adidas Yeezys or Nike x Sacais. On a man in mid-life, you want them odd enough to look less like efforts at youthfulness than marks of hard-earned eccentricity.

Robert Armstrong is the FT’s US financial commentator

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