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The Bespoke Techie

By Christian Chensvold

In a world of hoodies and sneakers, these men dare to take a little extra care when it comes to their office attire.

Andrew Poupart sports a cream suit made from vintage cloth from Fox Brothers, by Hemrajani. A shantung silk tie by H.N. White, shoes by Edward Green of London and a Panama hat by Bate’s Hatters, also of London, complete the look. Photo by Micheal Short.

Symbols of hierarchy are a coded language some men obsess over (the book and film American Psycho provides delightful black comedy on the subject), and yet one of the most astute analysts of sartorial semiotics was an Englishwoman named Pearl Binder, author of the 1958 tome The Peacock’s Tail: An Examination of the Purpose and Meaning of Male Dress, an erudite exegesis on the history of masculine panache.

Writing during the postwar years of gray-suited company men, Binder noted that male attire had become drab and dreary, which tells you, she argued, precisely how modern men feel about themselves. Men feel emasculated and demoralized for having, among other things, created machines to do their work for them. This was the era when the IBM corporation became a symbol of bland conformity, a punchline for beatniks and comedians. But the company’s strict dress code of gray suits and white shirts (never blue) is positively flamboyant compared to the puerile garb of today tech titans, whose sneakers and sweatshirts mark them not as Promethean gods and more like children playing with fireworks, blissfully ignorant of the consequences.

Yet amid the tech industry’s new hoodie-clad sartorial punchline (and paunchline) are a few rebel souls challenging the status quo by actually dressing like the affluent adult males they are, with respect for standards of personal attire above the lowest common denominator, and running the gamut from subdued to proud assertions of personal elan.

Casual attire may seem limiting to the novice who cannot envision anything beyond khakis and golf shirts, but it is in limitation, as Goethe observed, that the master reveals himself. Ian Anderson, who boasts a master’s from Stanford and has worked for several e-commerce startups, has a casual wardrobe with impressive variety. “I usually wear chinos and jeans with a casual shirt of oxford, chambray or flannel, with a smart piece of knitwear or a sportcoat,” he says. “Shoes are things like boots, loafers, derbys or minimalist sneakers.”

Ian Anderson’s blazer above is by Suitsupply, with trousers from J. Crew. Anderson’s outfit is accented by a cotton/ linen shirt from Proper Cloth and penny loafers by Crockett & Jones for Brooks Brothers.

The idea is to balance personal taste with the realities of the casual environment. “My guiding principle for dressing is to look put-together without standing out,” he says. “Wearing a three-piece suit to a startup’s office doesn’t make you any better dressed than wearing athletic shorts to a board meeting. Both are inappropriate and show a lack of situational awareness.”

Of course, sometimes one is acutely situation-ally aware, and prone to acting “inappropriate” on purpose. Take Andrew Poupart, a software engineering manager at Apple who runs an Instagram account of his dashing classic style called styleafter50.

Poupart wears a Hemrajani double-breasted suit in dark gray, nailhead worsted cloth, a shirt by Budd Shirtmakers and a tie in a vintage ancient madder, made by H.N. White in London. His shoes are bespoke, made by Nicholas Templeman. Photo by Michael Short.

“After a career spent in jeans and polo shirts, my kids grown, and losing some 30 pounds, I decided to start dressing in a manner I found pleasing — and that pleased my wife — expressing a side of my personality that had been dormant for many years,” he says. That includes looking like a gentleman from the Golden Age of Hollywood in double-breasted suits and Panama hats. “My colleagues either don’t care what I wear or simply don’t comment,” he says. “People at Apple dress however they want, and I very much doubt that I influence anyone else.”

But comments from one’s peers — especially peers made, however inadvertently, to feel self-consciously slovenly — are all but inevitable. Phillip Kim works in biotech and has engineered a wardrobe consisting of Harrington-style windbreakers, trench coats, and footwear such as Chelsea boots and longwings.

“I’ve always loved art and design and enjoyed the way good clothes can make you feel,” he says, “and appreciated the craftsmanship and detail that went into fashioning a garment.” But aesthetic sensitivity can be awkward in a world of philistines. “Once, for an audit by health authorities, I wore a navy suit with white shirt and repp tie,” he recounts. “Almost no one else had dressed like me, and one of the managers good-naturedly remarked, ‘Why are you making us look like assholes?’”

Sometimes clothing connoisseurship is driven by practical reasons, such as an unusual physique, and not the kind you might expect. Max Woolf, a consultant for startups, began ordering custom shirts to accommodate his inverted-pyramid torso, since mass-produced, off-the-rack clothes aren’t based on Hellenic ideals of anatomical perfection.

“One of the benefits of a custom shirt is the higher armhole,” Woolf explains, “which means the shirt seam sits in the correct position under your arm, which looks better and allows for range of motion. I’ve tried explaining this to a few co-workers, and they all think it’s ridiculous.”

He also knows there’s some-thing worse than being thought ridiculous, and that’s being thought a salesman. “I would never wear a sportcoat to a mobile gaming company,” says Woolf. “You’re met with wide-eyed looks of confusion, and people just assume you’re there to sell them something.”

There’s much talk in the tech industry of inclusivity, and surely that can be extended to men who were born infected by the clothing bug as well as those with Peter Pan syndrome. For why grow up, sartorially speaking, unless you actually want to? “Software engineering is not a job where how you dress matters,” says dapper gentleman Poupart. “I think people entering the industry continue to dress how they did in college, and that’s fine, as long as you can do the job.”

At the same time, we cannot escape the fact that man is a social animal and that we live in a material world. Absent complete information — which is our default operating mode — we make assumptions and judgments, including ones of hierarchy as expressed by attire. “I’ve attended customer meetings and brought people more senior than myself,” says Woolf, “and the customer will barely speak to them. I think it’s subconscious and the customer doesn’t even realize it, but they wind up speaking to me because of the way I’m dressed.”

He models a red and ecru striped blazer by Steed Bespoke Tailors, made of vintage cloth from Fox Brothers, and accented by a navy grenadine tie by Sam Hober. Photo by Michael Short.
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