IS IT TIME for Tim Cook to tuck in his shirt? Every time I see the Apple chief executive take the stage, as he probably will on Thursday at yet another exciting new product introduction, I can’t help wondering.
Much has been made, after all, of Apple’s recent cozying up to the fashion world: its supersecret unveiling of its watch to a few carefully chosen magazine editors last month; said watch’s introduction during New York Fashion Week; the pop-up display and dinners held in its honor during Paris Fashion Week; and its starring appearance on the cover of China Vogue’s November issue, attractively accessorized with a Céline dress and the model Liu Wen.
But as we enter the age of the wearable, might it not behoove the leader of such a brand to look the part? This is not a flippant question.
It is true that Mr. Cook does seem to have developed a signature personal style in the spirit of his predecessor, Steve Jobs, who wore a jeans-and-black-mock-turtleneck combo pretty much every time he appeared in public. To wit: a large, slightly wrinkled, untucked button-down shirt. Though the color may change (the shirt has appeared in varying shades of black, blue and even lavender), the form remains the same.
But unlike Mr. Jobs, whose look referenced a specific design language (Issey Miyake cool), Mr. Cook has a style that is more like the fashion of no fashion, to borrow an idea from George W. S. Trow. For a company that clearly wants to influence fashion, that is a confusing message to send.
Granted, there is a well-established tradition in Silicon Valley of tech entrepreneurs acting as if they could not care less about what they wear, including the hoodie-and-Adidas-sandal-sporting Mark Zuckerberg of Facebook and Dennis Crowley of Foursquare, who once attended a black-tie dinner in a zip-up sweatshirt and dirty sneakers.
The obvious point is that said baby geniuses are too busy thinking great and disruptive thoughts, and coding through the night, to spare a moment to worry about as mundane an issue as image.
It may involve as much reverse style snobbism and careful consideration as any coat-and-tie venture when you really think about it, but on the surface it’s a seductive mythology of mind over men’s wear. Certainly when it comes to Mr. Cook, it supports the shtick that his Apple is all about the product being the star, not the executive.
At the same time, though, Mr. Cook is also the face of the product — at Apple, that hyper-controlled company, above all. It’s not as if they trot out Angela Ahrendts, the elegant Burberry-dressing senior vice president for retail and online stores, or even Paul Deneve, the natty ex-YSL chief executive charged with special projects, to represent the brand.
Why should this matter? Well, partly because, as Peter Thiel, venture capitalist, founder of PayPal and Silicon Valley myth/billionaire, writes in a new book, “Zero to One”: “It’s a cliché that tech workers don’t care about what they wear.”
“Everybody from slackers to yuppies carefully ‘curates’ their outward appearance,” Mr. Thiel writes. And what that means in the tech world, he says, is that when it comes to dress, “everyone in your company should be different in the same way.” In other words: As the leaders do, so do the people who work for them.
Thus, as tech gets more and more into fashion, as wearables become the Next Big Thing, perhaps it is the moment to reconsider ye olde assumptions. And should not Mr. Cook take the lead? If Apple really wants to own the wearable space, should he not be the chief executive who breaks the stereotype? Is there not real opportunity to seize the high(er) ground here and change an antiquated culture?
Certainly, Jonathan Ive, the co-creator of the Apple watch, is not afraid to discuss his style evolution. In Paris to introduce his product, he was happily showing off a denim suit jacket made by his regular tailor, whom he called “Tom the tailor,” who does all of Mr. Ive’s tailoring. Tom, Mr. Ive said, used to work at the Savile Row name Anderson & Sheppard before moving out to the Lake District, and now the two collaborate on Mr. Ive’s wardrobe.
And he is not alone in taking a more creative and proactive approach to his personal dress. Yahoo’s chief executive, Marissa Mayer, has been breaking the fashion barrier, posing splayed across a chaise longue in Vogue, and talking about her fondness for Oscar de la Renta, Carolina Herrera and Armani.
Though Ms. Mayer has gotten some blowback from her willingness to reveal her wardrobe choices — mostly along the lines of, “Shouldn’t she be embarrassed to be seen caring about this?” — there’s a leaning-in aspect to her revelations that is laudatory. (By contrast, her female power peer Sheryl Sandberg, who also appeared in Vogue, leaned as far away from the subject of clothing as she could.) Also it is, probably, strategic.
Ms. Mayer, after all, has clear business designs on the fashion world, from Yahoo’s style and beauty verticals to possible video collaborations, and there is little doubt that her willingness to dress the part has helped advance her cause.
Similarly, Jack Dorsey, a founder of Twitter and Square, is known for his penchant for Prada. And while this is considered a notable idiosyncrasy in pretty much every profile of him recently written, chances are it is a boon when it comes to selling the idea of a mobile payment system to brands.
Like it or not, if you want to be taken seriously by an industry, it helps to appear as if you take it seriously.
Finally, and perhaps most significantly, one of Mr. Cook’s fiercest competitors, Satya Nadella, the newish chief executive of Microsoft, is also proving something of an uncharacteristic clotheshorse. Unlike previous Microsoft chieftains, Bill Gates and Steve Ballmer, men whose dress preferences tended, on the one hand, to the nerd-in-suits-and-sweaters look and, on the other, to the bruiser-in-suits-and-sweaters look, Mr. Nadella has made a practice of switching up his outfits, as demonstrated recently by a bonanza of pictures courtesy of various news reports sparked by his ill-advised comments about women and raises.
Here he is wearing a plaid jacket in contrasting shades of blue, blue shirt and jeans; there he is in a gray suit and white button-down. Here he is in a navy crew neck; there he is in a maroon T-shirt and color-coordinated pinstriped jacket. And so on. The only consistent principle is a perfect fit.
A perfect fit?
That is, when you come to think of it, a quite useful subconscious association to create. Mr. Cook might take it under advisement.