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The Women Who Love a Man in Heels

Mesmerized by their confidence and how their heeled shoes make their ass look like marble, women are falling head over heels for guys who dare to don a pair of pumps

Search Instagram for “men in heels,” and you’ll find 84,000 hashtagged posts, approximately three million “slay, queen” directives and a vast assortment of the most hazardous ankle-breaking pumps you’ve ever seen in your life. But most notable are the horny comments about these heel-wearing men. “You are a miracle of a human,” writes one anonymous Instagrammer on a photo of a muscular man pole-dancing in iridescent platforms. “Yummiiiii,” comments a middle-aged woman on a shot of a firm-assed gentleman rocking a pair of stiletto Mary Janes. You could bounce a quarter off of the man’s glutes, but his heels are the main attraction.

For the last few centuries, high heels have been relegated to women’s wear. They’re beloved for their leg-lengthening effects, high-fashion implications and general elegance, separating the dames from the unsophisticated, dilly-dallying dolls next door. But as designers and male fashionistas alike seek to skirt the gender binary, nose-bleedingly high footwear has become a bit of a men’s game, too. Brands like SYRO, Kira Goodey and Lidia Talavera are creating genderless heels in inclusive sizes. Wearers are posting their videos to Instagram and, increasingly, TikTok, where videos with the hashtag #meninheels currently have more than 82 million views. Someone’s grandfather even went viral for pairing masculine silhouettes with a tasteful pump. 

Meanwhile, in the masturbatory universe, there are currently nearly 90,000 Pornhub videos under the label “men wearing heels.” And while a lot of explicitly pornographic heel-wearing content is targeted toward gay men, plenty of women move through the world just waiting to live out their Dr. Frank-N-Furter fantasies.

First, though, a brief strut into the high-heeled annals of history. If you’ve seen a portrait of King Louis XIV, it’ll come as no surprise that heels were originally a primarily male style. In fact, some historians trace the origin of high-heeled shoes all the way back to the 10th century, when they were worn by members of the Persian cavalry. (Picture a fancy cowboy boot.) The aforementioned King Louis was known to rock a colorful stocking with his stylish slippers, allegedly issuing an edict stating that only members of his court could wear red heels. Unfortunately, heels made their way out of men’s fashion during the end of the French Revolution, resurfacing only as cowboys began to pepper the American West, relying on boots with an inverted round heel to stay comfortable on horseback, a la the Persian cavalry. 

Fast forward to 1947, when David Bowie, née David Robert Jones, was born in London. Despite a disturbing lack of archival evidence, one can assume that the infant Bowie somersaulted out of the birth canal wearing a glittery high-heeled brogue. Thus began a beautiful partnership between pop music and ostentatious footwear, starting with Bowie and Prince, leaping across the sea to influence male K-Pop idols, and culminating in Vogue calling 2019 “the year of men in heels.”

Since then, men’s heels have crept their way into our collective horny vernacular. Think, for example, of Harry Styles’ winter spread for Dazed that debuted last year. The capstone of Styles’ multi-outfit spread involved a slime-green archival Jean Paul Gaultier skirt set punctuated with Burberry kitten heels — and Styles wore the hell out of them, despite otherwise serving major Grinch.

Styles represents an interesting subset of the Men in Heels community; specifically, men who embrace feminine fashion while belting ballads about their hunger for pussy. For some women, that’s as sexy as it gets. After Styles’ spread, one blogger called him a “beautiful, beautiful man.” Another wrote about a fantasy in which Harry Styles joins Doja Cat in “stomping on my face with pink gogo boots and high heels.” Meanwhile, a Styles stan account posted photos of a different photo shoot and wrote “GOOD FUXKING MORNING TO THESE PHOTOS OF HARRY STYLES WEARING FISHNET TIGHTS AND HEELS ONLY.”

So what’s the appeal? 

For Cat, a woman in her mid-20s, men in heels represent a sort of introspective confidence that she finds irresistible. “[When I’ve worn heels], I loved the way they made me feel elegant and powerful,” she says. “It was a beautiful way to express myself, and I love that heels are another way that men could be more confident and comfortable in their body and attitude.” She notes that she’s lived the fantasy with several male partners who wear heels, including a recent partner who regularly joined her in shoe shopping.

For Taylor, a 30-year-old Houstonite, seeing a man in heels reminds her of what she calls her “sexual awakening” — specifically, seeing Tim Curry as Dr. Frank-N-Furter in The Rocky Horror Picture Show. “[It was when] he looks at the camera and says, ‘How ‘bout that?’ while strutting in the heels,” Taylor says. “He was so sexual, confident and in control. And his ass did look better. The patriarchy was right about that one.” She’s still trying to figure out her adult attraction to men wearing heels, although she sometimes wonders if it hinges on practicality. “It’s all the benefit of wanting to share closets and also do sex,” she says, noting that the “smorgasbord of gender fluidity” is a bonus. “Maybe because it feels like a role reversal?” she wonders. “Subliminally, it’s like the man is giving a nod to femininity, and therefore it gives me permission to feel more masculine if I want.”

Meanwhile, the objects of Taylor’s admiration are raking in the compliments. Twenty-five-year-old go-go dancer Bryant Santos explains that his high-heeled footwear isn’t just fashionable — it’s lucrative. “I began wearing heels when I started go-go dancing a few months ago,” he says, explaining that he’s a classically trained dancer and has always been drawn to the elegance of heeled dance. “I figured, what better way to start wearing heels and dancing in them than to do it at a gay club.” 

And while Santos’ club is geared toward gay men, he gets plenty of compliments outside of work. “In my personal life, I’ve also gotten great feedback from friends and family who love it and think they look great on me,” he tells me. “My mom is super supportive of it; she even offered to buy me a pair for work. I’ve also gotten great feedback from partners who like the androgynous aspect of it.” Of course, the tips at the club don’t hurt either. “When I started go-go dancing, my tips were decent in shoes, but when I started dancing in heels and wearing them around the club, my tips tripled instantly,” he says.

It’s easy to see what makes a man in heels so alluring. Yes, there’s the Frank-N-Furter-flavored nostalgia, as well as the sexiness inherent in defying an old-fashioned taboo. And regardless of the wearer’s gender, heels elongate the leg, boost the tush and flex the calf ever-so-slightly for a come-hither effect. But wearing sky-high heels also takes serious self-assurance, even for the women onto whom painful footwear is traditionally thrust. Seeing a man strut in a hazardous shoe suggests an immense confidence — the kind of confidence that Santos calls a “life-changing experience in all the best ways possible.” 

More than that, seeing a man — particularly a man who’s openly attracted to women — wearing a hot heel subverts the idea that men dressing in women’s clothing is inherently degrading or comical (or that there’s anything wrong with men being feminine). Think, for example, about those insufferable events during which college men “raise awareness” for sexual assault by racing each other down a catwalk in cheap plastic pumps. They may be walking “in her shoes,” but they do so in a way that makes it clear that the act of donning feminine footwear is pure comedy. Our culture’s newfound men-in-heels obsession is a mercifully far cry from that. 

Seeing a man wear heels without a hint of irony confirms what we’ve always known, if only subconsciously — that heeled footwear is sexy, no matter the wearer’s gender. It speaks to a simple truth: If you find a pair of shoes that make your ass look like it’s made of steel, you should wear those shoes. On that count, Santos puts it best. “Heels are empowering and are meant for everyone and anyone,” he concludes. “Whether you dance in them or strut down the street in them, everyone should experience heels at least once in their lives.” 

Nothing emasculating about that.