Clothes Don’t Define a Successful CEO

The long, slow slide into ignominy of Theranos, the Silicon Valley company that was once the poster brand for biotech breakthroughs, and its founder, Elizabeth Holmes, came to a seeming end last week with the announcement of the Securities and Exchange Commission’s charge of widespread fraud, and an agreement to settle.

Unsurprisingly, there have been the usual post-mortems and recriminations; the tsking over our desire to impart special powers to the young disrupters of the digital age; and our obsessions with the brilliant-dropout narrative and overinflated valuations built on unproven products.

For me, though, this tale has a different message, one that has to do with the risks and rewards of creating an instantly identifiable image. And I wonder: Will black turtlenecks ever be looked at in quite the same way again?

Yes, I am talking about clothes and the CEO. Before you scream, “Sexist!” understand this: Holmes happens to be a woman, but this particular teachable moment is one that could, and does, apply to anyone of any gender.

Her sartorial story is the underside of the Steve Jobs sartorial story. Both used practically the same garment as a signifier. But what at first looked like a smart strategy by Holmes, visually connecting her to a globally recognized game changer, has now backfired in ways that are relevant to us all.

Early on, Holmes seemed to absorb Jobs’ example reality distortion and her own mythmaking. If he was the original black mock-turtleneck wearer, she burst onto the public scene in his be-turtled image (though he paired his with Levi’s and New Balance sneakers, and she wore hers with black pants and black blazers or black puffer vests).

She saw the advantage of consistency in style, of adopting what had become the techie’s equivalent of the heroic uniform, at least as read by the outside world.

She understood that through the visual of relentless sameness, she could immediately grant herself a signifier that set her apart, that acted as shorthand for her own presence and that hinted at the Silicon Valley values of the mind: the belief, beloved by figures like Jobs and Mark Zuckerberg, that wearing the same kind of clothes every day frees the intellect from having to make pesky dressing decisions and thus opens up more cerebral space for making the kind of choices that really matter.

Indeed, when it came to her turtlenecks, Holmes told Glamour in a 2015 interview, just before things started to go south, that she had “about 150 of them” and had been wearing them since she was 8. It was presented as a default choice, but the irony is that it had the effect of making her instantly recognizable — just as Jobs was, in his black turtlenecks.

It conveyed, despite the caveats, discipline and rigor, not laziness. If someone can be so strict and dedicated with her closet, not flipping and flopping with the winds of change, imagine how dedicated she will be to her business mission!

Were you to make a caricature of Holmes — once the youngest female billionaire — she’d be wearing a black turtleneck, and everyone would know who it was, whether or not they even understood what her company did. How many CEOs can claim that?

Bloomberg Businessweek just featured the bald pate of Lloyd Blankfein, the CEO of Goldman Sachs, above the bald pate of his presumed successor, David Solomon — the point being that no one could really tell the difference. Not so with Holmes.

Little wonder, then, that it was impossible, almost from the get-go, to read a story about her that did not contain some variation of the qualifier “in her trademark black turtleneck.” Occasionally those reporters were accused of sexism, but it was less about associating women with clothes than associating an individual with an item and marveling at such single-mindedness of purpose.

With her blond hair and lipstick, her uniform set her apart from the hoodie pack as well as the suits, and made that Jobsian connection, giving her an aura of cool in the way that he was cool (and Apple is cool) but that most digi-geeks are not, when viewed by the non-digi world.

But such an individual uniform has a risk if you don’t live up to the promise. In the end, it’s the substance behind the style that makes the difference; what you wear becomes its expression. So already, what was once the symbol of her dedication has become the symbol of the backlash, with various columnists berating themselves for not “looking behind the black turtleneck.”

In the same way that Gordon Gekko’s suspenders and Michael Milken’s toupee became symbols of their greed, Holmes’ black turtleneck is starting to seem less a brilliant frame than a false front; a carefully calculated costume that fooled everyone into assuming she was more brilliant than she was; a symbol of hubris rather than success.

Those who live by the turtleneck, die by the turtleneck. It’s enough to make the otherwise derided pantsuit look like the ... well, smart choice.