Should Men Wear Heels? Why Kanye, Justin Bieber, and Harry Styles Are On To Something

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A few days ago, I received a picture of Kanye West via a work chat: It was a screenshot of the Kardashian-West clan’s precious Easter photo, showing a dapper, buttoned-up West next to Kim and their two cherubic children. The photo was accompanied with a question from my colleague: “Is Kanye wearing heels?”

The question wasn’t referring to whether the rapper had switched out his Yeezys for Kim’s strappy stilettos, but instead pointed to the fact that he was wearing a suede boot with a modest block heel. Did it seem so out of the ordinary? To me, no. (Though, I have a documented infatuation with obsessions for odd men’s footwear, like pointed shoes). But to Twitter, West’s heel-clad feet seemed like news, and users quickly sounded off as to whether or not the rapper had put some lift into his step. Yet, this isn’t the first time that West has dabbled with an elevated silhouette—nor has it been his most outré incarnation of the look: During Fashion Week in March of 2015, West wore velvet heeled boots to the Fall 2015 Givenchy show, consequently receiving a hefty amount of flak on social media.

Has West been bothered by the widespread criticism of his footwear? Possibly. But it mostly seems as if he doesn’t care. After all, there’s a sort of regal confidence that comes with a man who can wear a heel—not unlike that of a man who can pull off a sinister-looking pointy-toed shoe. In fact, as with the winkle-picker, men’s heels have a long, and even royal, history. Their ancestry is as macho as it gets and includes the burly horse riders of Persia (heels made it easier to keep the foot in the stirrup) during the 16th century. Eventually, they were adopted among aristocrats in western Europe, signifying the relationship between wealth and impracticality—the higher the heel and the more wobble that came with it, in other words, the more well-off the wearer was. One of the most well-known royal heel-wearers included King Louis XIV of France (reign: 1643–1715). He went as far as to implement a you-can’t-sit-with-us edict when it came to his haughty footwear, stating that only members of his court could sport heels painted in the monarchy’s signature red hue.

The trend of men wearing heels eventually died off during the Great Male Renunciation in the 18th century, a time period when men shrugged off the idea of detailed, polished dressing, leaving that aesthetic to women. But the heel eventually resurfaced centuries later, making a cameo during the glam rock era of David Bowie, later worn with funk in cuissardes form by Rick James, and in teetering, patterned booties on Prince. Now, men’s heels seem to be coming back as gender-blurring looks and nouveau-dandy styles are on the rise thanks to labels like Hood By Air and Maison the Faux.

Now, the formerly female-centric shoe is trickling down, off the runway and into the mainstream, diluted in Cuban and stacked heels and worn by celebrity crews. It turns out West is just one of many high-powered, social media–knighted men delving into the healthy-amount-of-heel look. Harry Styles has long worn a retro heeled look à la Jimi Hendrix, and stepped out last week, ahead of his Saturday Night Live appearance, in a pair of West-esque brown boots. A few months ago, Justin Bieber wore a black boot with a sturdy heel with his skinny jeans. Even former Republican presidential candidate Marco Rubio created a stir with his sleek footwear, wearing a pair of kicky black heeled boots in a widely snickered-at moment dubbed “Bootgate” by The New York Times. His Florsheim-brand boots had even been christened with the loaded style name “Duke.” Rich, right? But you have to hand it to him, and the others. It takes a self-assured, kingly attitude to confidently clack against the grain. You could even say these men are on the heels of something sexy.

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