The High Heel Is Fashion’s Most Conflicted Shoe

My love of heels goes back to middle school, and I’ve been flirting with Achilles tendinitis ever since. Over the years, my go-to pairs have evolved from block-heeled boots from Mary-Kate and Ashley’s Walmart line for tweens to another Olsen offering: strappy sandals by The Row. I have trained myself to float across subway grates in stilettos as if I’m walking on water. (You should see my calf muscles.) Back when I had a dating profile, my answer to the “hidden talent” prompt read “running for the streetcar in heels.”

And while a pair of classic pumps makes me feel like Rafael Nadal sliding across a clay tennis court in his custom Nike Air Maxes (agile, powerful, above average in height), for a long time, it also made me feel like an outlier.

With designer sneakers on the rise and the dominance of other closer-to-the-ground styles, like schoolish loafers and prim ballet flats, my height-maxing choice felt contrarian. Notable, if fictional, high-heel devotee Carrie Bradshaw was on an extended hiatus. And Kamala Harris wore her Converses on the cover of Vogue and on presidential-campaign trails. Then, when sweatpants reached their peak in the pandemic, I considered selling every shoe I owned above five centimetres. I’m glad I didn’t. Now, I can sense heels marching back to the fore.

And it’s not just a revived Carrie Manolo-ing all over her downstairs neighbour’s ceiling in And Just Like That. There’s data to back this up.

On the Spring 2025 runways, flat-shoe sightings fell by 15 per cent, as tracked by fashion data aggregator TagWalk. Anecdotally, on the Spring 2026 runways, two of the season’s biggest designer debuts—Matthieu Blazy at Chanel and Jonathan Anderson at Dior—presented elevated footwear. At Chanel, it was classic patent pumps with sturdy square columns, and at Dior, a parade of heeled mules embellished with oversized fabric rosettes and bow-adorned slingback stilettos with a D-shaped toe box.

And research from luxury resale giant The RealReal shows a 26 per cent increase in high-heel searches, with a 34 per cent increase in searches for Louboutins—notoriously high shoes. It seems that wherever I look, I’m no longer on tiptoes alone.

Why is this happening? A decade ago, fashion houses would delight us when they released their takes on the athletic shoe. Today, the designer-sneaker trick feels played out. The sentiment around athleisure is waning—you don’t have to look at Lululemon’s falling bottom line to sense that leggings have lost their collective hold over us (at least, outside of airports). Plus, Gen Z, the current torchbearers of youth culture, are growing up and office-bound. “They’re realizing for the first time that they have more shoe options available to them than sneakers,” says Timothy Chernyaev, a stylist whose popular TikTok account, Relax It’s Only Fashion, offers runway and celebrity style commentary. “Finally, they’re like, ‘Let me wear the Manolo; let me look correct,’” he says.

The word “correct” bears a load here. Maybe it’s because the high heel has historically been part of the “uniform of femininity,” says Elizabeth Semmelhack, senior curator at the Bata Shoe Museum in Toronto. That uniform, which typically also includes tight-fitting dresses, coiffed hair and a full face of makeup, has also been embraced by the right-wing political sect of the U.S.—the one dominating our grimmest headlines. “Whenever the high heel comes back, it brings with it a whole host of concepts,” says Semmelhack. The tradwife immediately comes to mind. I type “heel” into Thesaurus and related words that appear are “attend” and “obey.” Semantic coincidence or eerie indictment? Why do I love this painful shoe so much again?

“A heel brings with it all of these nuances that can be exploited or leveraged, depending on how you choose to wear them but also on who’s looking at you,” says Semmelhack. Sure, the Mar-a-Lago set might wear heels.

But so did flappers in the 1920s, along with shorter hemlines and new-found liberation. Platforms were favoured by the rebellious Teddy Boys and gender-bending Glam Rockers. And Martha Stewart wore heels during her days as one of the few women stockbrokers of the late 1960s. (She paired them with hot pants.)

It seems that wherever I look, I’m no longer on tiptoes alone.

“The right shoes do a lot for you,” says Elle AyoubZadeh, who worked in corporate finance before launching the luxury shoe brand Zvelle in 2015. Like me, she’s a devoted heel wearer, and in the beginning, her designs were an extension of who she was.

“I don’t make shoes that are meant to sit in museums,” she says. “I make shoes for people to live in and achieve things.” Her early iterations featured a heel that was thin but wide, so it looked like a normal stiletto from the side but was less likely to slip through subway grates or get caught in sidewalk cracks.

AyoubZadeh was travelling to Italy to visit her factories frequently and spending a lot of time in airports, observing travellers’ footwear. She decided to design sleek, high-quality dress boots and sneakers for men after being particularly put off by the shoes she saw male travellers sporting. The pivot worked—celebrities like Colman Domingo and Patrick Schwarzenegger are among the brand’s fans—and AyoubZadeh decided to shutter the women’s side of her business. Despite this, heels haven’t left the picture. Zvelle’s dress boots feature a slight heel (a fitting reference to the earliest iteration of heels, which was worn by the Persian cavalry to help them keep their feet in stirrups), and AyoubZadeh has toyed with making it even higher, based on feedback from a celebrity stylist.

Chernyaev is on the same page. “I can’t be at an event wearing a flat,” he says. “I need at least a Cuban heel.”

He’s not the only man looking for a little lift. On red carpets, heeled boots—and outright heels—have become a more frequent sighting on men thanks to celebrities like Sam Smith, Harry Styles and Cody Fern. For a more private gathering with friends, Chernyaev will opt for a true pair of high heels. (He owns several.) “I think there’s something so fun about wearing an uncomfortable shoe in the privacy of someone’s home,” he says. And heels are a non-negotiable when he’s styling a look. Even for a close-up shot of a model during a photo shoot, the shoes stay on despite being well out of the frame. “I’ve heard some models say ‘I don’t need heels; I can bring the attitude on my own.’ No, honey, you do,” he says.

“A heel brings with it all of these nuances that can be exploited or leveraged, depending on how you choose to wear them but also on who’s looking at you.”

Chernyaev lives in L.A., where heels are typically only spotted after dark. But he says there’s something charming about a heel that’s dressed down with, say, jeans. “People assume that heels always have to be really put-together. But lately I’ve been seeing people wear just a beaten-up pair of suede sandals or something. You can tell that they are comfortable in them and wear them all the time.”

I’d like to think there’s something equally charming about my oft-worn black Manolo Blahnik pumps, as classic and reliable as a cast-iron pan. The toe box has stretched and curved to the shape of my foot, and the leather is well creased from an immeasurable number of steps. I know it’s clichéd, but walking in them—arches taut, ankles tense, posture perfect—does wonders for my confidence.

I type “stiletto” into Thesaurus. Suggestions? “Bayonet,” “blade” and “sword.” Now I know why I’m so allured by heels: They represent many things. High heels are a symbol of submission and subversion. A weapon of vulnerability and a shield of bravado. A feat of engineering and an objet d’art. They are a walking contradiction.

This article first appeared in FASHION’s March 2026 issue. Read more stories from FASHION’s March 2026 issue here and subscribe to the print magazine here.