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T he point is to bounce, just a little. That’s the shoes’ way of telling you—a little wobble, a little give—that all is well: that the shock of your footfall, heelfloortoe, heelfloortoe, is being absorbed. Dolly Singh, the CEO of the shoe design firm Thesis Couture, is explaining this as I walk in a prototype version of footwear that has thus far been, due to limitations that are only partially technological in nature, pretty much impossible to imagine: shoes that are at once extremely high and relatively comfortable to wear. “What you should be feeling is, hopefully, a lot less pinch in the front than you normally do in 4-inch heels,” Singh tells me. “Because of this arch-support area”—she points toward the sole of the model I’m wearing—“it’s supposed to push your weight back towards your heel.” Related Stories All the Heels: Claire Underwood and the Case of the Stay-Put Stiletto

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What Does It Mean to Wear Heels? You know what? It does. Or, at least, walking in a pair of Thesis stilettos—whose shanks, and heels, are constructed mostly of dense, slightly flexible polymer (“ballistics-grade,” Thesis’s marketing literature points out)—minimized the reflex that walking in heels normally produces in me: the need to adjust my limbs and my overall self to compensate for my unnaturally raised foot. The shoes I’m wearing, Singh told me, are only about 70 percent completed, design-wise; still, even at the prototype stage, you feel that cushion and that give and that reassuring little bounce. You feel the shock of your walk being eased. You definitely would not run in these shoes, in the manner of Carrie Bradshavian fantasy; you could, however, very reasonably walk in them. At least for, you know, a little while. Singh, 37, is a former recruiter at SpaceX, Elon Musk’s rocket engineering firm whose offices in Hawthorne, CA, consist largely of hangar and factory space. She spent much of her time on that job walking—“about 3 to 4 miles a day,” she recalls—on hard floors that were particularly ill-suited to the wearing of heels. She wore them anyway: Working in an industry dominated by men, she appreciated the few extra inches of height the shoes gave her. (And also: the sense of professionalism, and of femininity.) It didn’t take much research to realize that many women, every day, live their own version of that compromise. So, when Singh left SpaceX, she recruited some of its employees—among them, yes, a rocket scientist and a former astronaut—to help solve a problem that is generally not treated as a problem at all so much as an unfortunate fact of ladylife: the insult and occasionally the injury that can come from the wearing of heels.

S tripped of their symbolism, heels are, simply, shoes like any other: objects that help to separate the human foot, which is inconveniently soft, from the surface of the earth, which is inconveniently hard. And yet, of course, heels do—heels are—so much more than mere footwear. In their teetering heights, they make audacious assumptions about fashion and feminism and professionalism and sex and privilege and power and its opposite, and about the way all those things, in the early 21st century, chafe against each other. Heels at once lift women up and hold them—hold us—back. And, of course: We choose, day by day and week by week and Special Occasion by Special Occasion, to let them do it. Heels are both a claim of femininity and a test of it. They are the bindings of the willfully bound. “I hate high heels, more than anything.” - Cara Delevingne In that sense, while Thesis’s comfortable heel represents a small feat, so to speak, it also represents a very large one: a counterargument to a longstanding assumption—rendered in fashion as well as in many other areas of the culture—that womanhood is defined, in part, by the ability to bear pain. Not just in the sense of “suffering for beauty,” as the saying goes, but in the deeper sense that the collision of those two things is integral to feminine experience. It’s an assumption that helps to explain why stilettos have become such quintessential symbols of womanhood; it also helps to explain why they are, as those symbols, so deeply unsettling. Heels hurt. They slow their wearers down. They occasionally trip them up.

What Thesis’s work suggests, though, is that the technology of the heel, the manufactured thing that takes its name from the natural one, could change the politics of the heel. The comfortable stiletto Thesis is promising is one that, simply because it hurts its wearers less, also demands less of them—and, by extension, of all of us. Thesis is certainly not the first company to claim to have made a comfortable heel. What makes its approach unique, though, is that it isn’t relying on low heel heights or thick heel widths or wide toe boxes or excessive interior padding—the stuff of dancing shoes and Naturalizers and their ilk—to improve its heels’ comfort levels. (“Comfort shoe,” indeed, is something of an epithet around Thesis’s sleek L.A. office.) Instead, the company reconsidered the architectural framework of the shoe. The people Singh recruited, from SpaceX and elsewhere, to advise Thesis in doing that work included Hans Koenigsmann, the (yes) rocket scientist. And Garrett Reisman, the (yes) former astronaut. And Matt Thomas, the former director of mechanical engineering at Oculus VR, the (now-Facebook-owned) virtual reality firm. And Andy Goldberg, an orthopedic surgeon. And Francis Bitonti, a designer—he created that iconic, 3-D-printed gown for the burlesque star Dita Von Teese—who has become an expert at using algorithms to ensure garments’ fit. Singh also brought on Amanda Parkes, a fashion technologist, to ensure that the shoes the company created would be stylish as well as comfortable. Not running-shoe-comfortable, to be extra-clear, but for-a-high-heel-comfortable. “What we’re fundamentally trying to do,” Singh explains, “is make a stiletto that feels like a wedge.” To achieve that, the team first replaced the thin, metal spike that supports the typical heel with one made of that ballistics-grade polymer. Just as importantly, though, they played around with the shank of the shoe—the base of the sole, the structure that does the all-important work of arch support—in order to distribute the wearer’s weight toward the heel and thus away from the ball of the foot, the source of so much orthopedic pain. Thesis’s S-curved shanks lead to shoes that concentrate only about 50 percent of the wearer’s weight there—an improvement from the current industry average of 80 percent.

The whole thing was much more complicated than Singh first anticipated. “I came from rockets and VR,” she notes. “I thought that six months after I started this project, I’d have the most amazing shoes that the planet has ever seen. And here I am, three years later—and I’m almost finished.” It’s appropriate, though, that creating those shoes would transform from a “project” to a broader purpose: The appeal of heels—not just of sky-high stilettos, but also of their less audacious cousins—lies, most broadly, in their ability to function not just as footwear, but also as small, wearable symbols of mankind’s tendency toward restless ambition. Heels have emerged from roughly the same impulse that led to cathedrals and skyscrapers and, yes, rockets: our desire to be taller, and grander, and generally more than we once were. “You never find wonderful and great things on the ground, but instead placed on high, to fill others with wonder and reverence,” Arcangela Tarabotti, a Venetian nun, argued in the 17th century. She was defending a very early version of the stiletto. “The core of my work is dedicated not to pleasing women but to pleasing men.” - Christian Louboutin So you can ask why heels, given all that they demand of their wearers, continue to be so popular—and, indeed, to be such easy tokens of femininity, used in everything from baked goods to office products to houses of worship. You can point out all the compromises, large and small, that must be made when a person—usually, but not always, a female person—buys, and wears, and navigates the world upon, a pair of upthrust metal spikes. You can say (as Carrie Bradshaw, that character who derived so hefty a portion of her identity from her Manolo Blahniks, might have): I couldn’t help but wonder … What puts the “I” in “high heels”?

But to do all that, fashion being what it is, you also have to acknowledge all the things we women gain, or are told that we gain, from the wearing of heels, aesthetically and professionally and otherwise. Thesis Couture plans to include just 1,500 pairs of shoes—retail price: $925 each—in its inaugural line, coming out this fall. At a recent soft-launch event, in New York, Singh announced to the assembled crowd that they could add their names to the waiting list of people who have expressed advance interest in purchasing one of those pairs. The list, Singh told me, currently has more than 10,000 names. So, yes: Let’s talk about the “I” in “high heels.” But first let’s talk about the we. Y ouTube, in its capacity as a massive, user-generated advice column, has many tips on offer about the best ways to walk in heels. The mega-vlogger Michelle Phan’s “How to Master the High Heel” tutorial—3.5 million views so far—provides an appropriately step-by-step approach. “Your first assignment when walking in heels,” she says, “is to find a straight line and follow it.” Phan pays particular attention to the distinct challenges presented by cobblestones (“for every step you take, you need to have a general awareness of where your heel is being placed”), and grass (“keep your weight on your toes”), and stairs (descending them, in particular, “it’s all about keeping a steady pace and a firm placement on each step”—but also, just to be safe, “use the handrail”). Phan also offers a more generalized tip for effective heel-ing: “Putting on your favorite upbeat song will help you get in the mood as you practice your walk.”

Phan’s tips are joined, and occasionally contradicted, by thousands more. Kassandra Brooks reiterates the importance of preparation when it comes to walking in heels: “Seriously, girls: practice, practice, practice!” she coaches. Victor Chu, a shoe designer who teaches a class about how to walk in heels, recommends that you “engage your abs—this gives you poise and control”—and “walk heel to toe, which transfers impact to the leg instead of the ball of the foot.” (Also, “relax your hips and knees so you’ll be fluid and graceful.”) Pooja from Glamrs.com recommends swiping deodorant onto the feet to minimize the friction of heels. (Ellebangs, for the record, says that the same blister-preventing effect can be achieved with baby powder.) “If [the shoes are] a little bit loose, you can always shove toilet paper into the front,” the model Cassandra Bankson points out. And Buzzfeed’s “ULTIMATE HIGH HEEL SURVIVAL GUIDE” offers, in addition to advice concerning Moleskin and gel inserts and Band-Aids, some broader coaching: “Don’t give up!”

The Heel Advice Industrial Complex—a collective composed mostly of women generously helping each other, but more broadly of people trying to make a side-door profit from the large and steadily expanding U.S. shoe industry—owes its size, and its longevity, to the fact that none of its tips have thus far succeeded in keeping their own promise: that heels can function, effectively, as footwear. “A shoe, like a building—or, on a much smaller scale, anything that supports or distributes weight in some way—requires architectural consideration,” Samantha Cataldo, who brought the traveling “Killer Heels” exhibition to the Currier Museum in Manchester, NH, told me. The discomfort of high heels—the fact that they ultimately fail at the job of being functional—is evidence, in that sense, of technological failure. And so is the fact that heels tend to make that most basic of human activities—walking—a little bit precarious. “Stilettos,” in particular: Their name comes from the Italian for “dagger,” but their shape suggests a broader menace. Heels that are both skinny and sky-scraping are the things that, in 1993, led Naomi Campbell to trip, dramatically, on Vivienne Westwood’s runway, the victim of the designer’s Super Elevated Gillie heels. They are the things that, in 2013, felled Jennifer Lawrence as she took to the stage to accept her Academy Award. They are the things that, in an episode of Sex and the City, found Carrie walking in a friend’s fashion show, swaggering in a pair of stilettos ... until, in short order, she tripped on them. There Carrie was, channeling Naomi: splayed on the runway, brought low by the very footwear she’d trusted to raise her up. It’s telling, too, that Sarah Jessica Parker, a real-life lover of heels, reportedly suffers from foot-related health problems. So does her fellow heelaholic, Victoria Beckham. (This is another of Thesis Couture’s main selling points: Its shoes are shots against the prevailing assumption that, as Singh puts it, “you get frumpier shoes, or you’re going to get frumpier feet.”) A study conducted in 2014 by the American Podiatric Medical Association found 38 percent of women saying they’d wear a shoe they liked even if it caused discomfort; another 71 percent said they already have a heel-related foot ailment.

Heels, indeed, are thought to be the cause of much of the roughly $3.5 billion that women in the United States spend each year on foot surgeries. The desire to wear them comfortably has led some women to get botulism—Botox—injected into their feet: Dr. Scholl meeting Dr. Frankenstein. That same desire is the source of “Haglund’s deformity,” a painful condition that has been given the revealing nickname of “pump bump,” and also of bunions and hammertoes and many more extremely preventable podiatric ailments. Each year, thousands of news articles are produced reiterating the health risks of heels. Each year, they are ignored. “Women,” the podiatrist Michael Liebow marveled to The Washington Post, “will wear their high-heeled shoes until their feet are bloody stumps.”

T he extremes of effort women put into the wearing of high-heeled shoes speak to something so obvious—or at least to something so widely assumed—that it seems silly even to specify: that heels are, in addition to everything else, sexy. When Beyoncé sings, in “Countdown,” “I’m all up under him like it’s cold, winter time / All up in the kitchen in my heels, dinner time” … it is extremely clear what she really means by “dinner.” Women wear heels, in part, to reap the benefits of their ability to lengthen the leg and firm the calves and protrude the pelvis and affect the walk in Darwinianly dutiful ways. Heels function, the University of Portsmouth psychologist Paul Morris and his co-authors suggested in a 2013 paper, as “supernormal stimuli”: Walking in them exaggerates “some sex-speciﬁc elements of female gait,” encouraging “greater pelvic rotation, increased vertical motion at the hip, shorter strides, and higher number of steps per minute.” Kara Gordon / The Atlantic That many women—on behalf, generally, of many men—seem to understand all this intuitively is the reason for articles like Cosmopolitan’s “20 Heels Men Find So Freaking Hot.” But here’s another thing—a related thing, and also a deeply conflicting thing—that many women seem to understand: that heels are, especially in the various knowledge-work industries, the expected foundation of a woman’s professional uniform. They are a much less comfortable, but equally conformist, version of the male suit-and-tie: a price of entry to a C-suite or a Senate office or any of the other places traditionally occupied by men. (See: Sheryl Sandberg and Marissa Mayer, TED-talking and speech-giving and otherwise boss-ladying in soaring stilettos. See also: Dolly Singh, walking miles a day in factories and in hangars and in heels.)

Which means that failing to wear heels, the logic goes, might even hold women’s careers back. As Marie Claire put it in a 2013 article about the sartorial—and professional—pitfalls of “casual Friday”: It gets tricky with shoes, especially flats, which for many women are a casual Friday mainstay. I’ve interviewed countless women CEOs, founders, and top-level execs over the years—not a single one in flats, which exude a kind of demure good-girl quality that rarely telegraphs power. If you’re ambitious, with your eyes steadily fixed on a corner office, you’d do well to save them for weekends and stick with pumps or kitten heels. So. Heels as power. Heels as sex, co-opted in the name of professionalism. Heels as, in all that, ambition. Avery Jessup, the hyper-ambitious Fox News reporter on 30 Rock, summarized the thinking perfectly: “Flats,” she declared, “are for quitters.” RuPaul would agree. Here’s another irony, though: The shoes women wear in the service of both professional expectations and sexual ones, shoes that at once celebrate and underplay the murky connections between the two, are often not really respected by … men in the workplace. The shoes that can bring women up to the level, physically and otherwise, of their male colleagues can also end up diminishing them. That might be because of incidental features—“nothing is more aggravating than listening high heels clicking on the tile at work in the morning,” the Twitter user David Schenk recently [sic] put it—but it is mostly because of high heels’ professional paradox: the fact that the default footwear of corporate conformity is so stridently suggestive of sex. According to the researchers Raj Persaud and Adrian Furnham, discussing Paul Morris’s paper, “Female baboons with a larger than normal swelling of the bottom, associated with the sexually receptive period of their cycle, arouse greater sexual interest in males. High heels similarly exaggerate the sex-speciﬁc aspects of the female walk, which could cause sexual arousal in males.” Taken to its extreme, the paradox accuses heels of emphasizing the body at the expense of the mind. At a tech conference in 2013, Jorge Cortell, the CEO of a healthcare startup, noticed a fellow attendee standing in a pair of very tall stilettos. He snapped a picture of the shoes. He then tweeted the picture of the shoes with the caption, “Event supposed to be for entrepreneurs, VCs, but these heels (I’ve seen several like this) … WTF?” He concluded his observation with a hashtag: #brainsnotrequired.”

Cortell’s creep-shot went viral; that is mostly because its caption rightly made people mad, but it is also because its assumptions struck a much deeper nerve. The tweet harkened back, on the one hand, to the Puritans of the Massachusetts Bay Colony, who tried women “who used footwear as an entrapment and seduction of men” for, yep, witchcraft. But it also reflected a more modern pitfall: the idea that heels are, essentially, a form of cheating—a strategy for compensating not just for a relatively small stature, but for a relatively small intellect. Which is not, generally speaking, a strategy that is available to men (many of whom would probably enjoy being a few inches taller). Thus: heel-shaming. Sole-policing. #brainsnotrequired-ing. “I’ve overheard conversations at academic gatherings,” the University of Exeter professor Francesca Stavrakopoulou wrote in 2014, “in which female colleagues have been described as ‘power-dressing’—coded language used to accuse a woman of asserting herself in overly ambitious ways.” “Women will wear their high-heeled shoes until their feet are bloody stumps.” - podiatrist Michael Liebow That tension—women, dressed down for the crime of dressing up—is on the one hand simply another aspect of the broader catch-22 that any members of a media-driven society must navigate every day: Look good, but don’t you dare be caught trying too hard to look good. But heels represent a particular strain of that paradox: Many men, though they may well love what heels do to the female form—there are of course many more than Cosmo’s 20 pairs of stilettos out there that men find so freaking hot—also seem to think that heels are, simply, silly. Steve Martin mocks them via his musical bit on “cruel heels.” The journalist Martin Daubney, after a day spent wearing six-inch stilettos, notes that “I finally understand why women say ‘it’s torture in these heels.’” One of the heel-try-ers in Buzzfeed’s “Men Try Heels For A Day” video complains, “This is a fucking mess—how am I supposed to walk in this?” Another declares, having gone through only a portion of his stunt-stipulated day in elevated footwear: “My thoughts on heels are very much the same as they were in the beginning: that they’re stupid.” His thoughts are, it turns out, part of a long-standing tradition when it comes to the gender dynamics of heels. In 1660, in one of his journal entries, the great diarist Samuel Pepys wrote, In the morning to my office, where, after I had drank my morning draft at Will’s with Ethell and Mr. Stevens, I went and told part of the excise money till twelve o’clock, and then called on my wife and took her to Mr. Pierces, she in the way being exceedingly troubled with a pair of new pattens, and I vexed to go so slow, it being late. Pattens—clogs, essentially, their wooden soles stacked upon inches-high metal rings—were one of the 17th century’s most popular forms of elevated shoe. Thus did Pepys and his wife join in a ritual that had been performed by many couples before, and that would be continued by many long after: a woman, struggling to walk in her high shoes; a man, struggling to disguise his annoyance at being slowed down.

A nd yet. And yet! Despite all of this—despite heels’ danger and discomfort, despite the tutting and the mocking and the difficulty walking … women keep buying heels. We keep wearing them. Reader: I keep wearing them! I, too, have dutifully pasted my DreamWalk® insoles into some bedazzled 3-inchers in preparation for a friend’s wedding. I, too, have tried to take Victor Chu’s advice to walk “fluidly and gracefully” in those shoes. I, too, have failed. The 3.5 million views Michelle Phan’s “How to Master the High Heel” tutorial has received since its posting in 2013 are signs of her overall popularity, sure, but they are evidence of something else, too: all the people out there who really, really want to achieve that mastery. “I think it is in our DNA as women to want to be peacocks and strut our stuff,” Tina Sloan, a longtime soap opera actor, put it. The “Killer Heels” exhibit at the Brooklyn Museum, in 2014, took visitors through a corridor whose walls were covered with Polaroids of women’s heel-clad feet. The images included Sharpie-scrawled captions the women had provided: single-word answers to the question of how the shoes made them feel. “Fierce,” read one. “Classic!” read another. “On fire,” read another. And also: “Wow!” “Cool.” “In charge.” “My thoughts on heels are very much the same as they were in the beginning: that they’re stupid.” - a guy, after a day spent wearing them So the answer to the why? of heels—why, in spite of everything, do women, by which I mean myself and maybe you, keep wearing them?—cannot simply be that heels are a commercial decision women make in the name of style. It’s much, much more complicated than that. Heels’ current desirability is the result of various cultural tautologies: They are attractive, basically, because we have told ourselves that they are. They are professional, basically, because we have decided that they are. They are what they are because of what we, all of us, are.

So the many factors at play in heels’ metonymic femininity make it extremely difficult to disentangle the Google search that leads people to Michelle Phan’s video from the conventional wisdom holding that heels, and specifically female bodies walking in heels, are hot. When Dita Von Teese announces that “heels and red lipstick will put the fear of God into people,” that may be the culmination of her own experience, but it is also the product of centuries’ worth of cultural input. So is the reality-star-turned-lifestyle-guru Kristin Cavallari’s decision to title her memoir Balancing in Heels. Heels are subject to all the assorted complexities that will be layered, parfait-like, onto any question of fashion. And yet the extremes they represent—the highs and lows, the aspiration and the acquiescence—make them especially apt as symbols for the current moment: one in which feminism’s various waves have evaporated, in some sense, into an air of possibility, and also of confusion. One that in many ways takes women’s equality for granted, and that in many others totally does not. One that is renavigating sex’s place in the workplace. One that is typified by a heel-clad Beyoncé—a wife and a mother and also pretty much the dictionary definition of “hot”—strutting onstage as the word “FEMINIST” flashes on a screen behind her. One that finds Mattel redesigning the feet of its Barbie dolls so that they are not permanently molded to accommodate heels.

It’s a moment that is unsure, basically, whether feminine footwear that evokes the swollen butts of baboons celebrates, in the end, empowerment or submission. “I do not improvise in heels. I improvise in sneakers. Why would I improvise in heels? It’s terrible.” - Amy Poehler And: It’s one that finds the wearing of heels—or, conversely, the non-wearing of them—representing much more of a choice than it did for those who came before. “Fashionable suffering is no longer obligatory as it was for our grandmothers,” Nancy Rexford, the author of Women’s Shoes in America: 1795 to 1930, puts it. “If a woman wears cruel shoes,” she adds, “we can be sure it is by choice.” And yet, of course, that “choice” will be informed by all the cultural and sexual and professional and sartorial expectations that can make shoes, symbolically as well as physically, uncomfortable. (Are heels sexist? Oh, totally. Or, well, maybe? How can you tell? (And also: Is makeup sexist? Or long hair? Leg-shaving? Bikini-waxing? Spanx?)) “It’s always seemed to me that the point was to be able to wear what you fucking well please, as I’m often quoted as saying,” Gloria Steinem explained. She continued, though: On the other hand, there are some symbols that were so forced on us in my youth that it’s hard for me to understand them as a free choice. Like girdles, garter belts, and very high heels that you can’t run in … but even if I felt internally uneasy, I don’t believe I ever was publicly critical of something another woman said she had freely chosen. So even Gloria Steinem, it seems, is a little confused about heels. Which is both reassuring and no help at all. The only thing clear at this point seems to be that heels, as symbols, require of the culture precisely what they require of their wearers: compromise. Carefulness. Step-by-step transactions. Heels give power and they take it. Michelle Phan chooses to buy stilettos; she works hard at walking in them; she gets confidence from wearing them. And yet her final piece of advice for wearing them on a night out is this: “Bring a pair of flats! And if you don’t have a pair of flats, get someone to carry you home!” Phan’s cheery tutorial cuts to video of her grinning as she perches upon the back of a gallant young gentleman. Together, they gallop off into the sunset, beautifully fused—two minds, two hearts, and one pair of functioning feet.

F urther complicating things is the fact that heels, pretty much throughout their history, have been designed by men. And men, in general, being the ones who will see the shoes but not wear them, tend to design heels with a focus on their aesthetics, rather than their ergonomics. Christian Louboutin, the moment’s reigning heel-maker, recently declared, without any apparent irony: “The core of my work is dedicated not to pleasing women but to pleasing men.” The stiletto, in particular—the shoe that serves, at this point, as the Platonic pump—co-evolved as an idea, the historian Elizabeth Semmelhack argues, with the invention of photography. Which was also, human nature being what it is, the rise of photographic pornography. The entrepreneurial pornographers of the 19th century clad their subjects in heeled shoes that would complement a woman’s legs as she laid and lounged, languidly and otherwise nakedly; the shoes’ presence in the photos reflected a desire, Semmelhack suggests, to prevent the models “from drifting into the allegorical realm.” (An airy goddess doesn’t wear heels; a regular, flesh-and-blood woman, however, might.) “I think it is in our DNA as women to want to be peacocks and strut our stuff.” - Tina Sloan, soap opera actor The images that arose from the collision of new technological capability and age-old human impulse served as formats for the ones that would come to permeate the culture later on—from advertisements (airbrushed pictures of women wearing little save for heels, used to sell everything from cars to stockings, to women as well as men) to the iconic “pin-ups” that would festoon the walls of so many bedrooms across the country. Those images did not, however, offer a format for actual footwear. Stilettos, as depicted in those commercial images, couldn’t yet exist as wearable, walkable footwear; it was not until the advent of modern steel production, in the 20th century, that functional versions could be fabricated. Only then—via the designer Roger Vivier, who would go on to liken his spindly, space-age-y shoes to “wearing dreams on one’s feet”—could the heels that had existed for so long as objects of male fantasy actually be worn by their putative consumers. Marilyn Monroe was, perhaps unwittingly, on to something when she declared, “I don’t know who invented high heels, but all women owe him a lot!”

Men’s heels, though, were also victims of a broader trend. “With the gradual rise of democracy and capitalism,” Valerie Steele, the director and chief curator of the Museum at the Fashion Institute of Technology, told me, “not only did high heels for men, but also color in clothing for men, jewelry, decoration, lace—all went out and became re-defined as being feminine rather than aristocratic.” Heels, because of that, “were now seen as effeminate: not acceptable for men to wear.” Indeed, when Napoléon crowned himself emperor in 1804, he made a point of wearing flats. The Napoleonic distaste for the heel endured, and expanded; it would be more than a century before men would dip their toes once more into heels, those “irrational,” “feminine” forms of footwear. Women, on the other hand—who would of course be dismissed as irrational regardless of what they put on their feet—continued, save for some dabbling in Classical-inspired flats in the early-18th century, to claim heels for themselves. The punishing paradox they represented back then—heels treated as both requirements for feminine beauty and evidence of feminine frivolity—will feel vaguely familiar today. As a New York Times article from 1871 (tellingly headlined “Make-believe Shoes”) proclaimed, Suffrage! Right to hold office! Show us first the woman who has independence and sense and taste enough to dress attractively and yet to walk down Fifth-avenue wearing … a show which does not destroy both her comfort and her gait. That mainstream dismissal of heels continued on into the 20th century—even as some men began experimenting with them again. In 1965, Time magazine announced that “somewhat alarmingly, teenage boys are taking to high heels.” Those boys would be imitated by, among others, John Travolta, catching Saturday Night Fever in high-heeled boots; and by David Bowie, strutting in his inches-high platforms; and by Prince, rocking stilettos; and by the members of KISS, whose elaborately heeled boots became anthemic to rocking and rolling all night/partying every day.

The men’s forays into elevated footwear, however, were fleeting, and aimed more at making a point than making an enduring style. For the most part, men-in-heels has been relegated to rodeos and drag shows. (Think, today, of the mockery recently leveled at former presidential candidate Marco Rubio when he stepped out on the campaign trail in inch-high boots.) No matter how much gender equality we claim to have attained as a culture—no matter how much of men’s fashion has become, in recent years, tighter and brighter and more flamboyant than it used to be—heels have remained, by default and by design, womenswear. And they have, in that, retained some of the Enlightenment-era dismissals of feminine fashion as impractical and, indeed, irrational. My thoughts on heels are very much the same as they were in the beginning: that they’re stupid. “Why do we wear them? They’re so painful. And pointless, really. You know, I really would like to urge everyone to stop it. Just stop it.” - Emma Thompson That is partly because of Roger Vivier and his introduction, in the 1950s, of the stilettos that managed to be at once futuristic and retrograde. The new shoe represented technological progress, via the thin heel of extruded steel that Vivier referred to as “the needle”; it also, however, with its height and its relative skimpiness, represented a new form of conservatism. Here was the cult of domesticity—the stuff born of Victorian ideals, the stuff that produced the ennui that Betty Friedan would later bemoan—neatly embodied in footwear. Here was Cinderella’s glass slipper, tiny and magical and impossible, rendered as sartorial expectation. Here was a design that was decently well suited for wear upon the carpets and linoleums and constraints of the home; here was a design that, tellingly, was not well suited for navigating the world beyond.

Stilettos, born of the porn of the 19th century, thus in the 20th adopted another dimension of male desire: the wish for loyal housewives—for women who would always be home, waiting for you and, indeed, on you. Because in those shoes, they couldn’t do much else. The stiletto briefly went out of style in the ’60s and ’70s, its dainty lines replaced with bold, stacked heels and very high platforms; by the ’80s, however, it returned—and came back taller than ever. And there it stayed. There was Tina Turner, icon-ing in stilettos. There was Madonna. There was Melanie Griffith, swapping sneakers for pumps as Tess McGill arrived—in every sense of the word—in Manhattan. There, a little later, was Julia Roberts, in Vivian Ward’s thigh-high—and toothpick-heeled—patent-leather boots. There was Naomi Campbell, in her Vivienne Westwoods. There was Jennifer Jason Leigh, whose Hedra Carlson took the “little dagger” on her feet to its murderously logical conclusion. There was Carrie Bradshaw, running on heels and then tripping on them. And there was Big, finally, proposing to her not with a ring, but with a diamond-encrusted pair of Manolos. And there, too, today, are Annalise Keating and Alicia Florrick and Claire Underwood and Selina Meyer, removing their heels and rubbing their aching feet after long days of bosslady-ing. There is Anne Hathaway’s Andy Sachs, the heroine of The Devil Wears Prada, telegraphing her (d)evolution as a character through her willingness, and unwillingness, to wear stilettos. There is Hathaway’s Catwoman, in a scene in 2012’s The Dark Knight Rises, asked by a male adversary, “Do those heels make it hard to walk?” There she is, kicking him from behind and purring in reply, “I don’t know. Do they?”

T hey do. Just a little bit, but they do! Heels’ failures as engineered footwear are precisely the reason Thesis Couture has more than 10,000 names on its waiting list: If heels can finally be made walkable—not in a “standing around at a cocktail party” way, but in a legitimate, “living one’s life” way—then that changes their politics. “The high heel is a mutable object—it is something that we simply assign meaning to,” Semmelhack, the shoe historian, told me. And if you can take the hobble out of the heel, that in some sense reverses the meaning that hundreds’ of years worth of history have assigned: heels as symbols, essentially, of a woman’s copious capacity—and, indeed, a woman’s willingness—to bear pain. And so while Thesis Couture’s promise of comfortable stilettos—informed by an intimate knowledge of what it means and feels like to walk in heels—is premised on fashion, it is rooted, too, in feminism. (There’s a reason Thesis nicknamed its first lookbook the “THE BOOK of LEGENDS,” and a reason, too, that each of the 21 designs it presents—the “Amelia Earhart,” the “Hua Mulan,” the “Serena Williams”—is named for a pioneering woman.) Thesis, through its emphasis on ergonomics and engineering, is fighting against the Louboutinian logic that has been with us, in some form, for centuries: the assumption that heels are feminine not in spite of all they demand of their wearers, but because of it. Kara Gordon / The Atlantic Singh and her colleagues, in other words, are hoping that their own contribution to the Heel Advice Industrial Complex will be to render all the tips and tricks that Michelle Phan and her fellow advice-offerers offer, finally, obsolete. The Thesis shoe is unsatisfied with Who What Wear’s advice, say, to “tape your third and fourth toes (counting from the big toe) together—we recommend nude medical tape for a low-profile look, but Scotch tape works in a pinch—to alleviate pain in the ball of your foot.” And with America’s Next Top Model’s J. Alexander’s suggestion that, when in heels, “whenever and wherever you can, sit, sit, sit!” (and then: “cross your legs so that all can see your beautiful, fashion-forward, painful footwear”). And it is outright indignant with Bustle’s conclusion that, if “stretching out your shoes” and “using Moleskin” isn’t enough to make walking in heels comfortable, then perhaps you should simply “change the way you walk.”

A Thesis shoe, to be sure—even after that first, extremely limited-edition line—will be accessible only to a small percentage of women. While future lines will feature designs at varying price points (including $600 for an evening look and $900-$1,000 for red carpet-worthy stunners), the least expensive of them, Singh told me, will be a “day look” for $350. Even the cheapest won’t be cheap. But Singh also hopes that Thesis shoes, if they catch on with the broader public in the way the company’s waiting list suggests they might, will have a trickle-down effect. Singh is expecting that Thesis’s design will be imitated—or, at least, that other designers will attempt that imitation. And that, all in all—six provisional patents notwithstanding—will be a good thing. Thesis’s broad goal, Singh told me, is to “fundamentally change the footwear industry and fundamentally raise the bar on how you make a good pair of shoes.” Or, as Kelly Shapiro, Thesis Couture’s chief legal counsel, explained to me of the company’s broad ethos: “We didn’t want to see our sisters in pain.” “I did everything Fred did, only backwards and in high heels.” - Ginger Rogers It’s notable that corsets, the devices that worked under the roughly heel-like auspices of “suffering for beauty,” were also hated by many doctors, loved by many men, loathed by many women, and tolerated by many more. They were the targets of many movements in favor of “rational dress” that arose, and died, in the 19th and early-20th centuries. Movements that, with convincing evidence on their side, accused corsets of “girl torture.” What’s notable as well, though, is that those movements were largely ignored by the broad public until fashion designers themselves began to create styles that de-emphasized women’s waists. Those designs brought with them a new implication, Valerie Steele told me: that women who kept wearing corsets despite the turn in fashion did so only in a vain attempt at insistent artifice. As Leigh Summers, the author of Bound to Please: A History of the Victorian Corset, explained it to me: “Older and overweight women probably continued to wear corsets well into the end of the 20th century”—at which point “pantyhose ultimately spelled their doom.” And so there, maybe, is another tautology when it comes to heels: They will stay in style as long as we—“we,” their wearers, “we,” their designers, “we,” their admirers—say that is where they belong. There have been “rational dress” movements in footwear, too—not just in the form of feminist objections to heels, but also in the guise of ballet flats and sandals and even wedges and platforms, which offer height while sparing the foot the concentrated gravity that comes with the wearing of stilettos. Those movements, for the most part, have done very little to reverse, or even to dent, heels’ popularity. As a representative from Zappos told me, “Heels are consistently a top-selling category for us, even as trends have shifted towards casual the past several years.” (She added: “Women will always have a need for heels. They are the ultimate feminine accessory whether in the office, a special occasion, or out for dinner.”) “I regret binding my feet. I can’t dance. I can’t move properly. I regret it a lot. But at the time, if you didn’t bind your feet, no one would marry you.” - Zhou Guizhen, survivor of foot-binding, 2007 What’s also notable, though, is that we seem to have arrived at a moment of widespread uncertainty when it comes to the underlying whys of heels’ wear. In 2015, the Cannes Film Festival met outrage when its organizers were reported to have turned away women who weren’t wearing heels from its red carpet. The festival organizers denied the report, but that didn’t stop it—flat-out rejections, all too literally!—from inspiring a string of anti-heel invectives. “Everyone should wear flats, to be honest,” Emily Blunt put it. “We shouldn’t be wearing high heels, anyway.” Kristen Stewart, who regularly wears sneakers on the red carpet, explained that while “in a photo, obviously, things look better wearing heels,” “in terms of just kicking around and actually, like, experiencing an entire night, heels limit me.” Many more young stars—which is also to say, many more young “influencers” and trendsetters—have been reflecting that same ambivalence. At an awards gala in 2012, Lena Dunham walked onstage in a pair of metallic high heels; a few sentences into the acceptance speech she was giving, though, she paused. “I have to take my shoes off, you guys, I’m so sorry,” she announced. And then: She did. Emma Thompson, similarly, took to the Golden Globes stage in 2014 holding her Louboutins in one hand (and, in the other, a martini). “I’ve taken my heels off as a feminist statement really,” she declared, “because why do we wear them? They’re so painful. And pointless, really.” Jennifer Lawrence has called heels “Satan’s shoes.” The supermodel Cara Delevingne, when asked what the worst part of being a model is, replied, “I hate high heels, more than anything.” Naomi Watts recently confessed that “I would never put on high heels unless I absolutely had to.” Miley Cyrus, in her song “Party in the U.S.A.,” humblebrags about her “outsider” status in L.A.: “All I see are stilettos / I guess I never got the memo.” “Oh, womenfolk, as we once burned our bras could we not torch the footwear crucifying us?” Mary Karr recently beseeched her fellow ladies in The New Yorker. She imagined the wonders that would follow that pump-pyre. “Our feet and spines will unknot, and high heels will fade from consciousness along with foot-binding and rib removal to shrink your waist.” Karr added: “The species may stop reproducing, but who the hell cares.” W hat does all that amount to? Will the heel, indeed, go the way of the corset and the bound foot—an icon of femininity rendered, via the network of advances we tend to shorthand as “progress,” obsolete? Could it be that the feminine ideals of the past will lose their cachet to the current influence of the nameless, faceless Cool Girl—the girl who wears Chuck Taylors and chugs beer and shoots whiskey and, in general, is hot precisely because she doesn’t try to be? Could it be that we have reached a moment when women’s fashion, taking a cue from the casual, comfortable impulses of the quiet luxurians and the coders of Silicon Valley, will do away with the high heel? Or, alternatively: Could the technological advances that define Thesis Couture’s footwear render all of those questions moot? Will all the forces bearing down on the heel as it currently stands be absorbed into Thesis’s ballistics-grade polymer? Could it be that the arc of fashion really does bend toward comfort? Possibly—but only possibly. This summer, Taylor Swift went on tour around the country and the world, performing for audiences of hundreds of thousands of people, many of them—most of them—young girls. Swift sang about confidence. She sang about romance. She sang about beauty. She sang the lyrics, “She wears high heels / I wear sneakers.” She did it all while clad in 3.25-inch Stuart Weitzmans.