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A gentleman’s guide to dressing your age

Read and learn, gentlemen

Like most men these days, I wear my vanity on my sleeves. I rarely dress my age, thanks to the prevalence of casual attire that’s cropped up everywhere. I seldom wear a neck tie anymore, somehow wind up wearing jeans whenever possible, and wear white sneakers with my bespoke blue suits. I invest more time and money into my hair and “beauty” regimen than my portfolio and flaunt enough rings and bracelets to pass for a gypsy.

Welcome to the age of middle-age male menopause. My mother always said I came out of the womb wearing a cardigan sweater and with the disposition of a middle-aged man. Now that I’ve actually reached the tender milestone of 40-something (give or take a decade or two, ahem), I can say with little debate I’m fairly smart, accomplished, and, for the most part, content. I’m also old. In other words, I’m not young, something which, in today’s society, is valued above all else.

In other words, I’m not young, something which, in today’s society, is valued above all else

Age is a bully you cannot dodge. Like a bad day, you can’t go back. None of which discourages us men from giving it our best. We’ve succumbed to fashion obsolescence, a sartorial malady once reserved for women who must stay current from year to year with the latest look. We gentlemen now too slavishly follow clothing trends on an annual basis to emulate the latest styles. So much for the noble notion of dressing for oneself. We’re all too busy eye balling one another’s “individual” look.

We’ve succumbed to fashion obsolescence, a sartorial malady once reserved for women who must stay current from year to year with the latest look

It’s the sort of farcical gesture that literally makes my toes curl (I now have hammer toes as a result). Blame it on the phalanx of leisure ware annexing our closets. There was a time when I actually wore a sports jacket on the weekend. Take out out the good ol’ tweed today and I might as well  bring out the walker and Miralax along with it.

Keep things simple

It’s not that I have anything against a well-made pair of $250 selvedge jeans. But when it comes to casual dress, there’s too much room and opportunity for the middle-aged man to commit fashion failure. He has no instinct for inherently youthful garb. He can’t help but look silly. More traditional menswear has endured for decades because men dressed for a reason. Each year there were slight, not seismic, changes in fit or cut. The influx of “casual everyday” at the office is so confusing that gentlemen don’t know whether they’re dressing for work or play. Our sartorial antennae are bent out of shape.

The influx of “casual everyday” at the office is so confusing that gentlemen don’t know whether they’re dressing for work or play. Our sartorial antennae are bent out of shape

The Italian gentleman can wear whatever he chooses because he knows the unwritten rules before he breaks them. It’s in his DNA. The effortlessly impeccable 50-something Milanese man couldn’t care less about his leathery skin, balding hair, or paunch. We should all look so well—and worldly.

Stop trying to follow trends

Is there anything more unflattering than a mutton dressed as a lamb? We’re bombarded by ads from retailers from Madison Avenue to the mall invoking us to overlook our metabolism (fat chance) and dress like something we’re not. Take the misguided J. Crew template of skinny suits with micro lapels, sneakers, and ties so narrow they could double as a bolo. Their mantra spread like a lethal virus. The dreadful faux pas of recommending a tie with your sneaker and suit aside, the purveying wisdom demands a suit about the width of a ruler which in turn calls for an equally narrow torso. Trousers worn ludicrously low at the hip rather than at the waistline only unfurl a shirt perpetually untucked and a protruding gut extending between your belt and the bottom button hole of a obscenely Daniel Craig-like tight jacket.

Is there anything more unattractive than a 45-year-old man projecting three to four pounds of pure man-tit when stuffed into a slim-fit button down shirt? Or packed into cropped, ankle-hugging trousers so tight that he can’t make it up the stairs. (So much for “the bigger the cluster, the better the luster”). A grown man in a graphic tee (“Kurt Cobain?”) is not sexy. Even worse: a novelty tee plastered with some Fendi monster or video game personality. A backpack slung over one shoulder befits a college student—not a businessman with an ill-advised Buscemi black leather backpack and matching high tops.

Is there anything more unattractive than a 45-year-old man projecting three to four pounds of pure man-tit when stuffed into a slim-fit button down shirt?

Avoid leather - at all costs

Leather in anything other than a jacket or bomber is not a good idea for those of us within striking distance of the Big 5-0. This would include leather joggers, t-shirts and hoodies. A hoodie is for your 20-year-old son. At least he owns a skateboard and doesn’t profess just coming from the gym in $1900 sweats from Vetements or the ass-hugging John Elliot.

“If a midlife crisis, I can understand it,” says Marcus Wainright, the CEO of Rag & Bone who never varies from his daily habit of a tee and jeans.  “But I don’t think it’s an age-related thing. You have to stick to the style you’ve always had and not really give a shit what anybody thinks.”

The same goes for designer David Flint Wood who after visiting Conrad, his 13-year-old son with partner India Hicks, felt vindicated after his son complimented him on his “uniform” of corduroy jacket, white “cheeno’s”, and a blue shirt. The sort of outfit not unlike the ubiquitous Instagram Steve McQueen, our icon du jour of casual cool, in his button-down shirt, v-neck, Barracuda Harrington jacket, off-white jeans, and Sander of England “Playboy” chukka’s. McQueen may be today’s trendy paragon of effortless comfort, but, in truth, he was a very traditional dresser, points out Robert Gillotte, bespoke manager at Turnbull & Asser in New York,.

“Most men don’t have the sense of style or the bodies to break the rules in leisurewear,” says the author Jay McInerney. “It is a lot harder than traditional. As more and more men get more casual, I find it almost an act of defiance to dress up.”

Left to our own devices, it’s harder to be creative casually because there are no guidelines and too many options. “There’s more room for creative expression within the more traditional canons of dress,” adds McInerney.

Don’t dress your age and commit the most heinous of sartorial sins: Trying too hard. You won’t look any younger. You’ll simply show your fear of appearing too old. What’s in the window isn’t necessarily what’s on the shelves. You can dress an old fart in Comme Des Garcon, but he’s still an old fart.

With Bright, Precious Days, Jay McInerney Brings His Yuppie Trilogy to a Close
The third volume recapitulates the strongest and weakest aspects of Brightness Falls and The Good Life.

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