My Week In Men’s Heels

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My Week In Men’s Heels

Words by Mr Ashley Clarke | Photography by Mr Sander Gabriel | Styling by Ms Sophie Watson

2 March 2020

Mr Ashley Clarke wearing his Gucci heeled boots

Ever seen a man in heels? Well, you’re about to. Usually the preserve of the fairer sex, heels are having a moment in the menswear world. Thanks to a smattering of celebrities and a few progressive designers, Cuban heels look to be a trend that’s grown legs over the past few months and who am I to argue?

At 5ft 7in, I’m neither a towering hulk nor a beanpole waif. I would look more at home in Hobbiton than I would on a Mr Hedi Slimane runway, and you know what? Most of the time I like it that way. But it’s 2020, a new decade. Why not wear Gucci heels for a week?

I’m following the example set by the fashion designer Mr Marc Jacobs who, in December, posted a characteristically outré photo of himself on Instagram sporting towering black Rick Owens heels. Mr Jacobs and I are not alone in our heel curiosity. Messrs Justin Bieber, Jared Leto and Harry Styles have all worn heels over the past couple of years.

Mr Kanye West, a personal icon and fellow short king, was seen wearing them as far back as 2017. They’ve been on runways and the red carpet more and more in recent seasons (Hood by Air and Mr Xavier Dolan are a couple of examples) and MR PORTER now stocks plenty of pairs, including the love-them-or-hate them Maison Margiela Tabi split-toe heels and a striking pair of patent TOM FORD Chelsea boots. Usually a Cuban heel, which basically means a solid heel of moderate height, is the leading style, but it’s by no means the only way to rock the trend. Just ask Mr Ezra Miller, who was wearing stiletto boots at this year’s Grammy awards.

When my chosen pair arrive, I’m a little apprehensive. Slick yet stompy with a chunky chain astride the vamp, they’ve been crafted in Italy from soft black leather. And they have “KITTEN” emblazoned in gold around the heel, which is just under 3in high. “They’re very Oliver Cromwell,” says a colleague. I think they’re the kind of thing a sexy and dangerous highwayman might wear if he crashed the Met Gala or a cocksure lothario in the court of King Louis XIII. My editor tells me I shall look like the Child Catcher in Chitty Chitty Bang Bang.

Heels made their debut in 10th-century Persia, where soldiers on horseback wore them to secure their feet in their stirrups. Later, the silhouette caught on in Europe with the upper classes, who wore them to appear taller and more formidable. Heels were popular with pioneering artists such as Sir Elton John, Mr David Bowie and Prince, who famously had 3,000 custom-made pairs and often jumped into the splits while wearing them.

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Invariably smart and statement-making, heels are proving to be a great antidote to the inevitable sneaker fatigue and can look surprisingly masculine when worn well. “A big part of why celebrities have begun wearing heels is the simple availability of them,” says Mr Christian Allaire, a style writer for US Vogue. “Brands such as SAINT LAURENT, Gucci and Celine have all debuted sleek Cuban-heeled styles in recent seasons. They are discreet enough for anyone who’s interested in the heel to try it without feeling too showy.”

Back to me. I’m not someone who believes in the transformative power of shoes. I am not Carrie Bradshaw, however much I wish I were paid $4 a word, but when I put on The Boots, my posture changes for the better. I might be only a couple of inches taller, but my confidence is at least 6ft 3in high. I feel more authoritative, more purposeful and look leagues sharper than I do in my usual hoodie and sneakers. I go out to dinner with my girlfriend, who, after initial reservations (“You’re doing what for work?”), now admits that I look “quite elegant, honestly”. Compliments come thick and fast. “Beautiful shoes, my man,” winks the restaurant maître d’. What can I say? I feel great.

Mr Allaire, a prolific heel-wearer himself, shares my enthusiasm. “I think my outfits look that much better with a bit of height to them,” he says. “Heeled shoes are an easy way to fix trousers that are slightly too long or wide. They also instantly dress up just about anything, especially jeans.” I know exactly what he means. The heels work as a kind of weapons-grade fashion catalyst that forces the rest of my wardrobe to sharpen up.

I have more of a silhouette to play with and, while I don’t ascribe to the idea that tall and thin people look better in clothes, the height that the shoes give me means my outfits appear undeniably sleeker. A vintage blazer that I struggle to wear because it’s slightly structured around the shoulders suddenly looks more proportionate, and a knee-length cashmere coat looks just that bit more expensive when I wear it with the boots. I can’t say the heels look great with my worn-out wide-leg Dickies (my usual uniform), but they look brilliant with a sharper pair of black trousers by Comme des Garçons. I found cropped trousers were the easiest thing to wear because I didn’t have to worry about the break and they allowed me to show off the boots more.

As the week goes on, I get more into my Gucci groove. Apart from that guy in the restaurant and the odd head-turn on my commute, hardly anyone else seems to notice them, which I tell myself means that I’m wearing them convincingly well. The key to styling heels, I have learnt, is to keep the rest of my outfit smart – no hoodies or belt bags, only understated tailoring or knitwear that won’t clash with the boots.

I click-clacked down the street like a pro, mostly pairing them with black trousers and T-shirts under dark-coloured cardigans or blazers. By the time I’m ready for my close-up in the studio later in the week, the leather has softened nicely into familiar creases. Yes, my feet ache after wearing them for five days on the trot (it’s become more of a strut, if I’m honest), but I’d say it’s been worth it.

If anything, I’m sad I’ve been missing out for so long. Every man should do a week in heels, at least. My wardrobe has been pushed to loftier places, figuratively as well as literally, and the boots make me feel more dapper. Will I carry on wearing them? Yes, I think I will. Don’t approve? Sorry, I can’t hear you from all the way up here.

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