The Style Debate: Should You Dress Your Age?

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The Style Debate: Should You Dress Your Age?

Words by Mr Mansel Fletcher and Mr Josh Sims

14 September 2023

Fashion may be beholden to the youth, but style, it’s widely agreed, knows no age. If anything, it makes more logical sense, in our view, that the ability to dress well – like any other skill or talent – should only get better as one advances through life, settles into one’s tastes and learns from the mistakes of the past. (Find us a guy who claims to have never put a foot wrong sartorially and we’ll swiftly spot a liar.)

However, whether style should change in one’s dotage compared to one’s salad days is up for debate – and any man who’s admittedly “getting up there” will have no doubt spent some time re-evaluating whether his wardrobe is still fit for purpose. (Is it time to ditch the distressed jeans now? Are we too old to be buying CELINE HOMME?)

To determine the rules – or lack thereof – around dressing as one reaches maturity, we asked two writers to battle out both sides.

Mr Mansel Fletcher, writer

01. Yes, evolve with age

In 1859, the news just in from Mr Charles Darwin, following his careful study of finches’ beaks on the Galapagos Islands, was that species evolve or die. I’d suggest that the silhouette and palette of a man’s wardrobe must, like birds’ beaks, adapt over time to an ever-changing reality. Darwin was looking at an evolutionary timescale measured in millennia. But when it comes to clothes, men need to develop their style at least once a decade. Let’s call it survival of the fits.

If, like me, you’re currently sailing through middle age, this can feel like unpalatable news. It’s tough to accept that there are things that you haven’t yet worn, and you’re probably never going to wear (leather trousers, for instance). That there are style avenues down which you’ll never walk. Sadly, there’s not necessarily any correlation between a man’s taste and his age, so we can find ourselves hankering after garments that are, at this stage of life, sub-optimal. I do a lot of hankering. Only with the full support of my family (I think the phrase is “cruel to be kind”) did I once resist the temptation to buy oversized Balenciaga sweatpants and sneakers in a risible bid for relevance.

If we have any hope of achieving our optimal style we have to step back and ask, “What is it to be stylish?” It’s when a man’s clothes chime with his personal and social circumstances. What’s right for a summer vacation bears little resemblance to what’s right for a formal party. Young, slim men often seem swamped by traditional tailoring, while bigger, more mature bodies, regardless of the shape they’re in, are rarely flattered by tight clothes. All different bodies can be well dressed, but different kinds of clothes are required to achieve this.

“Just make sure you’re expressing the man you are today, rather than dressing a memory of someone you used to be”

As time passes, our fashion choices should keep up with the developing reality of our bodies, our professional and personal lives and the world itself. A man who’s starting to contemplate his 50th birthday shouldn’t be dressing the same way that he did in his thirties because not only has his shape probably changed, so has the prevailing silhouette. The problem here isn’t looking like mutton dressed as lamb, it’s looking deeply unfashionable. If cosplay is your thing, and you want to re-enact the first season of Suits, then more power to you. Just don’t imagine that you still look the way you did in the early 2010s, or that such outfits carry the same connotations they did a decade ago.

So, how to move forward? Not by following some rigid guide to middle-age style. Instead try taking some slow, deep breaths, release your old ideas and find something new to love that speaks to your present reality. Perhaps fabric and texture are now more important than branding and logos. Perhaps you’re finally ready to smarten up in sharp tailoring, or to embrace comfort in quietly luxurious Italian sportswear, or only to wear blue, or orange, or even leather. Whatever your vibe is, just make sure you’re expressing the man that you are today, rather than dressing a memory of someone you used to be.

Mr Josh Sims, writer

02. No, stick to your guns

If you were to have popped by my house over the summer, you would most likely have found me in some combination of baseball caps, graphic T-shirts, oversized khaki shorts, white socks and Nike Dunks. Some, no doubt, would find my style about 30 years too late. I am now, as my children keep gleefully reminding me, “in my sixth decade”. Nonetheless, I’d say dressing my way was always preferable to me than the alternative.

Like Received Pronunciation, there’s a suffocating Received Good Taste at this age. I saw it in full effect in a gathering of luxury car industry bigwigs recently: white open-collar business shirt, short navy blazer, slim trousers cropped above the ankle, no socks and moccasins. They all wore the same kind of artsy bead bracelets and statement watches, too. They were cardboard cut-outs of each other.

They were also missing a trick: the older we get, the more assured we should be of dressing as ourselves, not as mannequins. Surely one benefit of middle-age is a confidence to be your own man, and to not much care what other people think. You like it. You wear it.

For centuries, that wasn’t possible. Any male dressed as a boy and then, to mark a transition into adulthood, dressed as man. Like every man, in fact. Sartorially speaking, each boy became his father. Respectability was conflated with uniformity. That ended with the youthquake of the 1960s. Then, as now, there was a reason why the choice in clothing was suddenly so vast. And that’s because, once it has served its function to protect you, clothing became about expression of the individual self, unconstrained by social expectations.

“Dress as you please. As Mr Clint Eastwood put it: ‘Don’t let the old man in’”

Of course, there are many occasions when these expectations remain important: when some expression of respect is due; and sometimes, though less so now than ever before, in the workplace. But to willingly take on other, arbitrary constraints to the way we dress is self-defeating. And perceptions of what is proper at certain ages – in dress as in behaviour generally – is one of those constraints.

Such is our blinkered obsession with youthfulness that invariably these constraints are directed upwards only, by the younger towards the older. You don’t get the middle-aged telling twentysomethings that their style is too old, that they should put away their charcoal three-piece suit and find some low-rise skinny jeans ASAP.

Indeed, one section of society dictating how another section of society should dress is indicative of how they’ve imbibed the Kool-Aid of the advertising tropes in which we all swim, but which some of us learn to reject. More seriously, it reeks of ageism – one form of discrimination we’re all, if we’re lucky, going to face. Those young ’uns questioning my skater style might like to keep in mind.

This isn’t to say that there aren’t items of clothing I would not wear that someone much younger might: sleeveless T-shirts, flip-flops, three-quarter-length trousers. That said, I would never have worn such hideous things when young, either. But the proscription of certain clothes for anyone no longer in the first flush – says who? – has no logic to it at all. It’s just another form of control.

So, rise up, you craggy gents. Dress as you please. As Mr Clint Eastwood put it: “Don’t let the old man in”.