Illustration by KIRSTEN ULVE
Over the course of six seasons, there was nothing Carrie Bradshaw (the character Sarah Jessica Parker made famous on Sex and the City) wouldn’t do in heels: strolls in the park, shopping outings, rooftop barbecues, brunches, dog walks, running down cobblestone streets after said dog, check, check, check. Even when she wasn’t stiletto sprinting, Bradshaw’s signature walk, a brisk trot that is often lovingly mimicked on TikTok, could qualify as a feat of athleticism when performed in four-inch Jimmy Choos or Manolo Blahniks.
Age didn’t dim her stiletto devotion. Fast forward to the first season of sequel And Just Like That… when Carrie is recovering from hip surgery and therefore relegated to, gasp, flats (which, she says, she hasn’t bought in more than a decade), the one physical goal she shares with her doctor is simple: “to get back into heels.”
While Carrie was eager to retire her flats, some women nowadays feel the opposite. “Almost every woman I work with has a love/hate relationship with heels – 99.9 per cent of them say they love heels, but they just can’t wear them any more,” says Joy Asibey-Gabriel, a personal stylist based in Toronto. Asibey-Gabriel’s client base is predominantly successful and entrepreneurial women in their 40s and 50s (ahem, Carrie’s age). Many of them have, says Asibey-Gabriel, gotten to a point where it’s less about following a trend or looking attractive for someone else’s gaze, and more about dressing for their own pleasure – and comfort – first.
If the pandemic wrought anything style-wise writ large it’s a need for comfort at every touchpoint of our outfits. “Fashion has embraced a more down-to-earth approach,” adds Sagal Mohammed, editorial and creative lead at Google Shopping, which closely tracks trends.
It was the sneaker boom, and a much broader demographic wearing them in a wide range of social settings, that first pushed heels out of favour, says Lorna Hall, director of fashion intelligence for trend forecasting company WGSN. “Any heel resurgence was then further quashed by the pandemic, which pretty much entrenched sneakers and comfort-shoes dominance as it casualized our overall approach to dressing and footwear,” she says.
At Holt Renfrew, Carolyn Wright, senior vice-president, product, reports that while customers don’t want to sacrifice comfort, they are still craving fashion novelty. “Customers are moving to a low-profile, slim, vintage-esque sneaker and a flat, ballet silhouette,” says Wright, pointing to the Miu Miu x New Balance collaboration.
Asibey-Gabriel has found herself steering clients who speak wistfully about heels but can no longer handle or rationalize wearing them toward more manageable versions such as a block or kitten heel (she loves the Brother Vellies thigh-high boot version).
Google searches for kitten heels are currently at an all-time high in the U.S. and Canada, and Hall says that the best-performing heel styles on e-commerce this season were more support-giving shapes such as platforms, slingbacks and low heels.
The same is true at Holt Renfrew where customers have gravitated toward lower heights. “People are embracing a hybrid work lifestyle whereby a work wardrobe isn’t defined by the traditional codes of corporate attire and because of that there’s been increased demand for lower heel heights, loafers and ballet flats,” says Wright, who calls out Prada’s sculptural-toed kitten heels as her new favourite.
Maili Wong, 45, a senior wealth advisor in Vancouver, rotates between flats, chunky heels and high heels, too. “They just provide an elevated look,” says Wong, who turns to Jimmy Choos for that touch of heightened polish. When she started her finance career on Wall Street in New York 20 years ago, Wong says there weren’t many women working on the trading floor, but the ones who were all wore heels every day.
Some women, such as Toronto litigation lawyer Elham Ellen Jamshidi who has an Instagram account called “Lawyer in Heels,” still wear them every day. Walking to the courthouse, she’ll throw on a kitten heel, but when she’s in the courtroom it’s stilettos all the time. “When you walk into a courtroom with heels you give main-character energy, and being a lawyer you want to exude that confidence, you want people to listen when you speak and you need to have that presence,” explains Jamshidi, who loves Gucci and Gianvito Rossi styles but says most of her heels are Christian Louboutin. “Every time I win a big case I go out and buy myself a pair of Louboutins as a reward,” says Jamshidi. She has more than 200 pairs.
But while comfort has been imprinted into our collective consciousness, Hall reports there has recently been a tentative resurgence of heels, which she credits in part to the return to formal fashion trends and more in-person events and occasions. “Also, for Gen Z this is the first time they have gotten the chance to dress for the office at all and they are experimenting with their identity,” says Hall.
For women who can pull it off, no matter what their generation, a high heel can be a style power move. “It lifts you up, changes the way you walk and hold your body, and it does feel powerful,” says Asibey-Gabriel. Elevating the leg also creates a line that has visual appeal, which is why on the red carpet heels are usually ubiquitous. But that is changing, too: Margaret Qualley, Jane Fonda, Rebecca Hall and Isabelle Huppert (among others) all walked red carpets this year looking stylish in flats.
Of course one woman’s power move may not be another’s: What makes women feel confident and beautiful, sartorially speaking at least, is entirely individual. And while ease has taken on a new level of importance in recent years, adaptability, says Wright, has too.
Shoes have to carry women through the many transitions between their day and night because they often simply aren’t carrying an extra pair. “There’s a lot more resistance to things that are not comfortable or practical,” adds Hall.
And as the cost of living continues to rise that resistance may follow. “When we have less cash to spend, a shoe style has to be more relevant to our lifestyles in terms of how often we will actually wear them,” says Hall. “And it’s heels that are more likely to fail when consumers apply this value equation to their purchase decisions.”