You’ve seen the photos. Harry Styles at the Met Gala. Mark Bryan, the engineer who wears pencil skirts and stilettos to the office. Lil Nas X rocking platforms on a red carpet. It’s easy to think a man wearing high heels is some brand-new, radical statement designed to break the internet. But it isn't. Not even close.
Honestly, we’ve just forgotten our own history. If you could time travel back to the 17th century, you’d find King Louis XIV of France strutting around in five-inch heels with red-painted soles. He wasn't trying to be feminine. Quite the opposite. He was showing off that he was so rich and powerful he didn't need to walk on dirt like a commoner. Heels were a symbol of status, military prowess, and "manliness" long before they ever hit a woman’s closet.
Fast forward to today, and we’re seeing a massive resurgence. It’s not just for the runway anymore. Regular guys are buying Chelsea boots with a three-inch block heel or high-end Rick Owens "Kiss" boots. They’re doing it for the height, the posture, and—frankly—the vibe.
Why Men Started Wearing Heels in the First Place
Let’s get into the weeds of the history because it’s actually fascinating. Persian cavalrymen in the 10th century used heels for a very practical reason: they helped the rider’s foot stay in the stirrups. If you’re trying to shoot a bow and arrow while galloping on a horse, you need that stability. When Persian diplomats traveled to Europe in the late 1500s, the European aristocrats saw the shoes and thought they looked rugged and exotic.
They adopted the look immediately.
It was a total flex. It said, "I have horses, I have money, and I don’t do manual labor." By the time the 1600s rolled around, the heels got higher and more decorative. Eventually, women started adopting the trend as a way to "masculinize" their own outfits, which led to a sort of fashion arms race. Men made their heels thicker and clunkier; women made theirs daintier.
Then came the Enlightenment. This was a turning point. Suddenly, men’s fashion became all about "rationality." This meant plain colors, flat shoes, and the death of the flamboyant male. This "Great Masculine Renunciation" is basically why men’s clothing has been mostly boring for the last 200 years. We’re finally starting to move past that.
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The Modern Shift: From Subculture to Mainstream
If you walk through Soho or parts of East London today, seeing a man wearing high heels isn’t a shock. It’s a Tuesday.
The shift happened slowly, then all at once. Rock stars like David Bowie, Prince, and Mick Jagger kept the flame alive in the 70s and 80s. They used the "stack" heel or the cuban heel to create a silhouette that felt larger than life. It wasn't about "drag"—it was about being a rock god.
Nowadays, the luxury market is catching up. Brands like Saint Laurent, Gucci, and Balenciaga have integrated heels into their menswear collections for years. The "Suede Wyatt Boot" by Saint Laurent is a classic example. It has a significant 40mm heel, and it’s worn by everyone from tech bros to rappers.
But why are more guys doing it now?
- Height. It’s the most obvious reason. A two or three-inch boost changes how you look in a suit or flared jeans.
- Posture. Heels force you to stand up straight. They shift your center of gravity.
- Aesthetics. Sometimes a flat sneaker just ruins the lines of a high-fashion outfit.
The Physical Reality: What It’s Actually Like
Let’s be real for a second. Heels hurt if you don't know what you're doing.
Men’s feet are generally wider than women’s, and our bone structure is different. Most "women's" heels aren't built to support the weight of a 200-pound man. This leads to a lot of crushed toes and snapped heels. However, designers specifically making heels for men—like Syro or even some of the more inclusive luxury brands—account for this. They use wider toe boxes and reinforced shanks.
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If you’re a man thinking about trying this, you can’t just jump into a four-inch stiletto. You’ll wreck your ankles. Start with a Cuban heel. It’s a slight slant that gives you some height without the instability.
Common Misconceptions
People assume a lot when they see a man wearing high heels. They assume it’s about gender identity or a specific sexual orientation. While that’s true for some, for many others, it’s purely about the silhouette. It’s architecture for the body.
There’s also the "pain" myth. Yes, cheap heels are a nightmare. But a well-made, Italian-leather boot with a stacked heel can be surprisingly comfortable for a full day of wear. It’s all about the pitch—the angle at which your foot sits. If the pitch is too steep, you’re essentially walking on your tiptoes. If it’s balanced, it’s manageable.
Expert Insight: The Psychology of the Heel
Dr. Elizabeth Semmelhack, a senior curator at the Bata Shoe Museum and author of Standing Tall: The Curious History of Men in Heels, has spoken extensively about this. She points out that high heels have never been inherently "female." They are a blank canvas onto which society projects its current values.
Right now, our society is valuing individual expression over rigid traditionalism.
When a man puts on a heel today, he’s reclaiming a piece of history that was taken away during the 18th century. It’s a power move. It’s saying, "I’m confident enough in my masculinity that a shoe doesn't threaten it." That’s a very different vibe than the performative "toughness" we’ve seen in the past.
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Buying Guide: Where to Actually Find Them
You can't just go to any mall. Most standard shoe stores stop at a men’s 12 (which is roughly a women’s 13.5 or 14), and they rarely carry anything with a lift.
- Luxury Brands: If you have the budget, Saint Laurent and Rick Owens are the gold standard. They understand the masculine heel better than anyone.
- Specialty Labels: Brands like Syro specialize in "heels for everyone." They use larger sizing and wider widths.
- Vintage/Thrift: Look for 1970s "disco" boots. They were built for men and often have incredible craftsmanship.
- Fluevog: They’ve been doing gender-neutral, high-heeled boots for decades. They’re weird, they’re chunky, and they’re built to last.
Making it Work: Styling Tips
Don’t overthink it. If you’re nervous, treat the heel like a regular boot. Wear them under a pair of straight-leg or slightly flared trousers. The hem of the pants should hit the top of the heel. This elongates the leg and makes the look feel integrated rather than "costumey."
If you’re going for a more "fashion" look, skinny jeans or even skirts (if that’s your thing) work well with a higher, thinner heel. But for the average guy just wanting a bit of an edge? Stick to the "Beatle boot" style. It’s timeless.
Practical Next Steps for the Curious
If you're interested in experimenting with height but aren't ready to go full "Louis XIV," here is how to navigate the transition without ruining your feet or your confidence.
- Measure your feet in centimeters. Don't rely on US/UK/EU sizing, especially when crossing "gendered" shoe lines. Centimeters are universal and will help you find the right fit on international sites.
- Invest in insoles. Gel inserts at the ball of the foot make a world of difference. Men aren't used to having all their weight pushed forward onto the metatarsals.
- Practice at home. Walk on carpet first. Get used to the shift in your center of gravity. Learn to lead with your hips, not your knees.
- Start with a 40mm heel. This is roughly 1.5 inches. It’s noticeable but won't make you feel like you’re walking on stilts.
- Check the material. Suede and soft leathers will stretch to accommodate a wider foot. Patent leather or synthetic materials will not. If you have a wide foot, avoid plastics.
The trend of the man wearing high heels isn't going away because it isn't a trend—it's a return to form. Fashion is cyclical. What was powerful in 1650 is becoming powerful again in 2026. Whether it's for the height, the history, or just the sheer joy of wearing something beautiful, the heel is firmly back in the masculine wardrobe.