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Feelin’ High: Men’s Heels Are Back

If lace, pink, and crop tops aren’t out of the question, why not men's heels? Based on menswear presentations, they’re yet another feminine-leaning semi-blast from the past that made a comeback this year.

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However, don’t automatically correlate high-heels with stilettos. Yes, gender-neutral stilettos are becoming a thing, as pointed out in The Daily Beast the Syro company has been creating a few versatile, solid-black styles for men, transgender, and nonbinary customers. The “it” menswear heel though has a bit more body.

Specifically, the stacked or Cuban heel looks like something you’d find on a cowboy boot and adds just a bit more height to footwear staples – think ankle-height Chelsea boots or lace-ups.

Beyond Americana-leaning interpretations from Celine, Calvin Klein, Gucci, and Maison Margiela, seasoned pop performers like Justin Bieber, Shawn Mendes, and Harry Styles have all been spotted in this ‘70s-esque silhouette.

Before you go out and don a pair (or attempt to navigate them on public transit), here’s what you should know:

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Men Wore Heels First

These days, whenever you envision women’s footwear, a pair of pumps automatically comes to mind. Usually, they have a stiletto on them – or perhaps something a little wider – but a heel feels practically definitive at this point.

There’s a reason flats fall under the category of “casual” footwear, even when you dress them up with embellishments and metallic fabrics.

Centuries ago, this wasn’t the case. Although the high-heeled shoe appeared in Western Europe at some point during the 17th century, historians estimate that Persian cavalry started sporting them during the Middle Ages, likely during the 10th century.

The design was purely practical at the time, featuring a raised base that made it easier for the wearer to hook his feet in stirrups when mounting a horse. In battle, the configuration helped the wearer stable himself as he operated a bow and arrow or lance while on horseback.

Black boots with heels for men

During the course of the 16th century, the combination of the growing textile industry, expanding the Persian Empire, and Europeans venturing out into other continents likely brought the heeled shoe over to Western Europe.

Unlike in Persia, though, the heels simply acted like a height enhancer. With Louis XIV (ruling from 1643 to 1715) as the paradigm, the shoes turned ornamental, featuring very elaborate designs, while a few extra inches gave the wearer a more powerful appearance.

Unfortunately, while heels eventually became an upper-class status symbol, particularly in France, the wearer couldn’t actually get that far in them.

Similar to the present, womenswear in the 18th century borrowed a few men’s styles, including the high heel. Although historians claim women were initially mocked for wearing this trend, the tables flipped, and the shoe gradually assumed an effeminate reputation over the next few decades.

By the time the 19th century rolled around, high-heels were strictly for women.

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While women’s styles evolved over the next several decades, men's heels didn’t actually return until the 1960s.

At this point in time, they resembled the era’s thick platform shoes – chunky base with a block heel – and only got groovier as the ‘70s progressed. Think an angular appearance with more color-blocking and flashier elements.

By the ‘80s, however, the trend all but disappeared, worn exclusively by flamboyant rockers, from Prince to Motley Crue.

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Men's Heels Shoes Today

To start, don’t refer to them as “high-heels.” That comes with a whole bunch of feminine implications, especially when many silhouettes could pass as gender-neutral.

Instead, the style is more of an elevated boot – or, in some cases, a boot with a taller “stacked” heel. Beyond the heel itself, the rest of the shoe often resembles a low to mid-height boot – slip-on, zipped, or lace-up, with a smooth, nearly detail-free exterior.

With this template in mind, here’s how you can attempt this trend:

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Start Basic and Neutral

Sure, patterned and embroidered options exist, but ask yourself this: “Realistically, how will this statement style fit within your wardrobe?” Chances are, it’s an anomaly that matches only your black skinny jeans.

Rather than go all out, aim to be versatile. Color-wise, stick within the realm of black and brown leather – or synthetic if that’s more your thing – and look for a smooth, rounded toe.

Because you’ll likely be tucking them under your pants, make sure it’s fairly close-fitting and has few accents or details. While they might be inspired by cowboy boots, they're still different from what to wear to a rodeo.

Black boots with heels for men

Look to Americana Influences

That said, the iconic cowboy – in authentic and cinematic forms – exists within the broad pantheon of Americana imagery. While this gives you some idea about what the shoe should look like, it further presents a more gender-neutral, if not masculine-leaning, way of approaching heeled shoes.

For one, lean away from its more ostentatious history – no bellbottoms and gold chains, in this case – and get inspired by classic western wear.

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To start, pick a heel no more than three inches tall. Then, start off with denim – a light to medium wash has the broken-in quality you’re looking for.

Make sure the cut is wide enough to cover just the top part of the boot but shouldn’t fall all the way down to the heel. Generally, a modern skinny jean should do, while a boot-cut pair offers a slightly wider and straighter fit for a more traditional look.

As far as the rest of your outfit is concerned, keep it neutral and classic – a plaid button-front or a T-shirt, accompanied by a blazer, trucker jacket, or a bomber.

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Try Them Out and Get Practice

Never worn men's heels before? Instead of purchasing a pair online, see if you can try a few on in a brick-and-mortar store to make sure the fit is something you really want to wear.

Sometimes, what looks cool on the page ends up feeling uncomfortable once you try it on.

Black boots with heels for men

Then, once you’ve picked out a style, take it for a spin at home before going about your day. As a general observation, you’ll likely have to shift part of your weight to the front of your foot, as having that thick block right under your heel takes some getting used to.


men's heels

Ivan Yaskey is a Philly-born menswear fashion blogger and copywriter. When not writing about men's style he's also an EDM and synthpop enthusiast.