When Mick Jagger married Bianca Macías in 1971, wearing sneakers with his Tommy Nutter suit, he made a real statement. Half a century ago, high and low culture did not often mingle casually. Of course, they hardly blend together in 2021: we dress all the time now, and the high style only survives at the margins. Trainers are omnipresent in all contexts and in all age groups. We live in a world of sneakers. All other shoes play a supporting role.
That this represents a test for older men is evident from the fact that many of us fail. Potential Jaggers with a pair of goofy designer sneakers that stick out from under dress pants are found at every party. Often times it feels like a sad stab at youth by someone who better go for middle aged gravitas.
But the right pair of sneakers look great. As with everything, it’s about choosing carefully. So start with a little taxonomy.
First of all, if there is a true classic sneaker out there, this is a smaller category than is commonly thought. I have seen 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 indentations in the blue rubber cores. Sperry, probably. A close equivalent can be purchased today (£ 75, sperry.co.uk). Sure, they look aggressively preppy but, worn with shorts, they are way better than the dreaded docksider or boat shoes.
Next classic: the Converse All Star. Cheap, versatile, laid back but (in off-white canvas) somehow mature. In black, always slightly punk rock. Despite a lot of effort, however, you can’t wear them with a suitable suit or pants, because they just aren’t substantial enough. They get lost in handcuffs. Their close cousins, Jack Purcells, with a slightly thicker soul and heavier profile, fare a bit better here. A nice new pair, in summer, with a light suit? Sure.
The next, much bigger category is Generation X nostalgia sneakers. These are the sneakers my generation adores because we wore them growing up. Adidas cap toes, Sambas and Stan Smiths; Canvas vans, with and without laces; Classic Puma suede; Nike Air Jordans, Air Forces and Waffle sneakers. The backtracking trend has made it all easy to buy again. The strategy here is simple: wear the ones you wore when you were a kid and be happy.
Another big group is what I would call the new classics, which weren’t around in the 1980s but feature an old-fashioned style. The Nike Blazers go here, as do the Onitsuka Tigers. A slightly darker Japanese brand, Moonstars, is my favorite (in purple). They are a parent of Converse All Stars but they are of better quality, with better detail. If you find a pair, buy them.
While I like to wear sneakers that echo the ones I wore as a kid, I choose much stronger colors than the ones I had in seventh grade. Indeed, apart from the classics of the web, I think there is a general rule here. With sneakers, subtlety should be avoided. If you are going to wear a comfortable, casual shoe in a setting that requires a bit of style or formality, the only way to do it is to go for it – especially if you go with a high top outfit / shoes. combo. The sneakers should scream.
Which brings us to a category to absolutely avoid: the ‘cool’ or semi-formal sneakers that, in their desperation, the brands and department stores that once sold real men’s shoes are now pushing us. In glossy white, black or brown leather, they pathetically try to fake “real shoes” and often have price tags to match. The whole is sad. Even cheaper normcore sneakers get me down. The switch to dress up was supposed to be fun.
The chunky foam-soled New Balance 990 in blue is certainly a genre in its own right – the king of all daddy’s shoes. They are a big “go to hell” to any fashion idea, and maybe there’s something to be said for that. Again, however, I don’t see the fun.
And the point is to have fun, which is why if a grown man doesn’t go with a totally classic sneaker then the stranger the better. Try Adidas Yeezys or Nike x Sacais. On a man in his forties, you want them to be weird enough to look less like youthful endeavors and more like hard-earned marks of eccentricity.
Robert armstrong is the American financial commentator of the FT
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