What Does It Mean to Wear Heels?

Today in shoesplaining: Until your career is at its height, ladies, maybe you should stick to flats.

Mike Segar / Reuters
It went like this. At a reverse-demo event in New York last night, Jorge Cortell, the CEO of the healthcare startup Kanteron Systems, noticed a female attendee wearing shoes. He snapped a picture of the shoes. He then tweeted the picture of the shoes. This is what he said:

Event supposed to be for entrepreneurs, VCs, but these heels (I've seen several like this)... WTF? #brainsnotrequired pic.twitter.com/Z1vBKxlLzo

Sexist! the people cried. No, it's not! Cortell responded. His #brainsnotrequired musings were merely protective, he explained, of the health of the shoe-wearer. And, by extension, of the health of us all. Heels are dangerous. Heels are dumb. High-heeled shoes are not, as it were, "sensible shoes."
But, of course, shoes are not merely shoes. Shoes, like any other clothing choice one must make every day, reveal something—inconveniently, maybe, but inevitably—about the wearer. Chuck Taylors say something. Sambas say something. Adidas shower shoes say something. And, yes, stilettos say something.
The question is what they say. What Cortell was suggesting with his off-handed "WTF?" comment (and with the #brainsnotrequired tag that accompanied it) is that the stiletto-wearer he creep-shotted was putting superficial concerns—appearance, attractiveness, style—over matters of a more pressing variety. (Comfort, perhaps? The ability to run a 10k at a moment's notice?) His tweet was suggesting, essentially, an inversely proportional relationship between depth of intelligence and height of heel. It was suggesting, as well, that the footwearer in question was somehow attempting to game a system based on meritocracy using something else: femininity.
Heels, essentially, are cheating. Heels, essentially, are wrong.
We can debate at another time whether heels are, indeed, the high-fructose scourge of the shoe world. The issue here is their place at a tech demo—an event that finds participants rewarded, ostensibly, on the strength of their ideas and execution, rather than their style. Heels, of course, are more fraught than their fellow-shoes because they're gendered in a way that the others aren't. Stilettos are Lady Shoes. And, as such, they carry, along with an actual lady, the baggage of hundreds of years of freighted femininity. It's easy to see them and all their contradictions—bold and teetering, leg-lengthening and stride-impairing, empowering and constraining—as representative of the precarious path walked by many women in tech.

In the Valley, as the AP noted earlier this month, "women who rise to the top tend to be judged more, both by men and other women, and in order to succeed they do have to dress better." And the women in the echelons of the industry, certainly, have their heels and wear them, too. Marissa Mayer, whose love of high fashion has become a significant aspect of her public persona, posed for a Vogue profile wearing statement stilettos. Sheryl Sandberg's Time cover co-starred her heels. Some women in the Valley, Claire Cain Miller wrote in the Times last year, "worry that they will not be considered serious technologists if they care about clothes." But "many are confident enough to dress the way they want to."

And yet—here is the catch of it—the sartorial statutes of the tech industry at large assume the opposite: that to dress well is, indeed, to be hiding something. To pay obvious attention to one's own appearance is to protest too much. Mark Zuckerberg wears hoodies because he can, but also because they remind all who behold him that he has better things to think about than his clothes. Steve Jobs did the same with his black mock-turtlenecks. (Though it's worth noting that the Apple founder's symbols of sartorial laissez-faire were designed by Issey Miyake.) As Lizzie Widdicombe wrote in a recent New Yorker profile of Brian Golberg, the aspiring entrepreneur "tends to wear baggy polo shirts, purchased in San Francisco, where, as he puts it, 'the schlubbier you are, the more credibility you have.'"
Time and attention are zero-sum things, and to devote too much effort to one's appearance is to take effort away, implicitly, from one's other pursuits—professional success among them. "The perception in Silicon Valley is that if you dress well, you couldn’t possibly be smart, or you’re in P.R. but couldn’t possibly run a company," Leila Janah, founder and CEO of the job-connection site Samasource, told Miller.

Which is to say, it seems that the tech industry has not only a glass ceiling, but also a shoe ceiling. Once you're in the C-suite, you can wear heels as high as you want; until then, heels may earn you a creep-shot and a "WTF?" from men who are meant to be your peers.

The problem with that is not only the double-standard for women working in the same industry; it's also that many women who aspire to leadership roles would prefer not to wear hoodies and shower shoes as they work their way up. Many women would rather wear shoes that make them look a little bit taller—that raise them up as they raise themselves up. As Janah put it, "I remember briefly attempting the Adidas and jeans and sweatshirt over T-shirt look, but I realized I was trying to dress like a young tech geek, and that just wasn’t me. Fashion is expressing my aesthetic sense just as much as our website is."
So what's an ambitious woman to do? To heel, or not to heel? Gloria Steinem and Betty Friedan and the other founders of the women's movement fought against the constraints of traditional femininity: They wanted not only equal representation, but also freedom from social pressures that came at the expense of women's careers. Those pressures were embodied, in some sense, by the heel. The movement's success, however, has meant that femininity is no longer a force; it is, or at least it is more than it's been before, a choice. Which means that #havingitall can negotiate its lines not just according to work and family, but also according to work and fashion. Wired's cover girl this month is, literally, a girl. She may be the future Steve Jobs, Wired declares. And even if she's not, she is likely the future in some other way. It is revealing, perhaps, that this symbolic tech-worker-of-the-future wears a uniform. And that you cannot see her shoes.