If Men In Heels "Freak You Out," Then You're Part Of The Problem

Photo: Bettmann/Getty Images.
I remember the first time I wore heels. Of course I do. And I remember the first time I fell out of them, too. It was a pair of sandal wedges — Mudd, I believe — and the left-foot strap was broken and the edges frayed by the clench of a shoe-obsessed dog. My ritual went a little something like this: I'd rush to my mother's closet and strap them on as soon as my parents left the house; I'd practice my walk, just like I'd seen the supermodels do, then meticulously put them back exactly how I'd found them. I never got caught. But after a Halloween costume that involved a set of my sister's booties and a broomstick, I never wore them again.
However, my childhood memories pail in comparison to the amount of people whose lives are threatened daily for wearing this accessory out in public. Take Alok Vaid-Menon, who can paint a vivid picture of how unsafe it can be for someone who's non-binary and transfemme to walk down the street in a pair of platforms. Or Rayne Nadurata, the gender fluid model who remembers how empowering it was to wear heels for the first time, and how the shoes, in turn, drew hateful slurs from passerby.
What was once an instant confidence boost has now turned into an accessory that, whether we like it or not, acts as some kind of gender identifier. Because if you're wearing heels, you're either a woman or want to be one — right? (The latter, by the way, is something that could get you killed in some cultures.) The act of propping oneself up in a pair of stellar height-enhancers has become such a fragile topic that even the most masculine, high-profile men can't even wear a heeled boot down the street without being bullied.
Photo: Andrew Lipovsky/Getty Images.
Take Republican senator Marco Rubio, who has earned no pity, but was roasted early last year for wearing a pair of Florsheim boots whose Cuban heel seemed to be just an inch above the Internet's acceptable level for men. Several members of then-rival Ted Cruz's campaign mocked the senator on Twitter, with Cruz's communications director publicly tweeting, "A Vote for Marco Rubio Is a Vote for Men’s High-Heeled Booties." Even Jimmy Fallon took the piss. Rubio was reportedly unamused by the unexpected chatter, but it serves as a reminder that, apparently, real men are a lot more down to earth — literally.
On the opposite end of the spectrum, see Harry Styles. Surprisingly enough, the boy bander is both heralded and heckled for his love of Beatle boots. Styles has been on quite the fashionable press tour for his role in Dunkirk, and Twitter can't seem to leave his heels alone. People are, allegedly, freaking out. But, after several seasons of high-heeled male models on the runway (y'know, where most trends are born), why are we still doing this?
Moving beyond the fact that heels have been a part of men's and women's wardrobes since the Dark Ages — and were once a signifier of superiority and class — the great Men In Heels debate has somehow maintained its steam despite the hypocrisy that's wedged between both arguments. In retrospect, it'd seem the question of who gets to wear them is a loaded one: The inquiry has become more of a reflection of the insecurities of those asking it than the actual subjects who wear them.
Photo: TopFoto/The Image Works.
But in our never-ending curiosity that is a set of hairy legs in a pair of boots, how oblivious have we become to the heel-bearing men we love? You may not have realized this, but we — yes, we, as a society — have been praising men in heels for decades. To name a few: Little Richard, whose heels were encrusted with rhinestones; The Beatles, whose customized take on the Chelsea boot became a part of their signature look; David Bowie, who traded his own Cuban heels for stage-ready, sky-high platforms; Prince, whose heels could be likened more to stilettos than anything else; Justin Bieber, Kanye West, and finally, Styles, whose funky footwear repertoire has become the subject of many elevator chat since parting from One Direction.
All of these modern men — mostly musicians, as a matter of fact — have paved the way for heels to appear on guys on and off the stage. But that's why it's societally "acceptable" for them, the rich and the famous, and blasphemous for those of us who go relatively unprotected wearing heels in everyday life. And because menswear continues to be held back by the idea that men's wardrobes should be no frill (while we continue to play with women's fashion, leaving the freedom of expression of men behind), it makes their resurgence on Styles poorly timed. But all is not lost, so long as we stop judging books by their covers, and instead take a walk in someone else's shoes.
But seriously, perhaps the most frustrating part of this conversation is the debate on what constitutes a heel or not. If three inches is too far, then are two inches the new one-inch? They're just shoes. And they contain a pretty cool, wild history, just as most iconic wardrobe staples do. A direct descendant of the flamenco boot, the Cuban-heeled Chelsea boot has survived and evolved an endless cycle of trends and their decades: the Beatles era of the '60s, the punk movement of the late '80s and early '90s, and now, the pointed-toe craze that's strutting across the runways, from New York to Milan. By arguing whether or not a heeled boot falls under the heel umbrella at all, we forget how cool it is the boot is still being worn, especially by such a mainstream, "hunky" heartthrob as Styles.
Photo: David M Benett/Dave Benett/WireImage.
By no means is Styles some arbiter of British style, nor is what anything he's wearing inherently new, but the guy's a great vehicle for several forgotten eras of menswear to make their way back to the red carpet. Where he might choose to perform on Good Morning America in a pink Disco-inspired suit (not to be confused with the era of Glam that rocked the '70s, from Detroit and London), there's a chance he rehearsed earlier that day as a Teddy Boy. Or a Soulie, the men of Northern England who birthed DJ culture. Or, for his next premiere, as a Zazou from a 1940s, shell shocked Paris. Because that's what rock and roll is all about: There's no beginning, and no end.
As we wade through the era of identity politics, where men and women — cis, trans, non-binary, and questioning — are targeted and scrutinized for who they are and how they choose to express that via their clothing choices, it's important to note that wearing heels as a man does not make you feminine, just as any other pair of shoes does not make you gay or transgender. What once started as a joke has now given way to fashion publications to revert back to the old status quo of telling people what to wear, instead of inspiring them to dress from the heart. We should never get to the point where fashion isn’t fun anymore.
A man's interest in style, no matter the color of their shirt or the height of their heel, should not be a litmus test for their masculinity. And, at least for the next decade, the feat of wearing heels, even a Chelsea boot, should be celebrated as an act of bravery. Because this is fashion we're talking about: the forward-thinking, imaginative, protective armor that has the power to transcend anything and everything in its way. But this disconnect between empowering people through clothes that make them feel good versus what's "in" or "out" defeats the idea that our closets — even our mother's — are a safe space. And for some, in more ways than one.

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