These are the most comfortable heels I’ve found to wear at work

In my quest to find an ergonomic (and elegant) option, I wore each pair for a full day and walked at least a mile outdoors.

These are the most comfortable heels I’ve found to wear at work
[Photos: Mari/iStock]

I believe in dressing up for work. Maybe it’s left over from years of wearing a uniform to school (there’s something seriously studious about a blazer and a button-up) or perhaps the right outfit just gets me in the right frame of mind to be productive. Science and employers agree.


While the old song enthuses, “you’re never fully dressed without a smile,” for me, the finishing touch is the shoe. And I prefer high heels.

Let it be known that there is no dress code at Fast Company. No one is forcing me to stuff my feet into heels. I’ve been known to sport a stiletto while working from home as well as in the office. Lately, though, as my commute has shifted to include even more walking to and from public transportation, my beloved heels have become a challenge.

Sure, I could stash them in a bag and change at work. I carry a tote that is fitted with a special pocket to keep them away from the contents of the interior. But my bag is heavy enough, and I don’t want to add the bulk of a pair of shoes to make it more awkward to sling over my shoulder. I just want to put them on my feet in the morning and take them off at the end of the day.


So when I read my colleague Liz Segran’s reports on radical redesigns of high heels—mainly from female entrepreneurs—that were assiduously crafted for both support and style, I was intrigued. The promise that you could walk, stand, and sit more comfortably sparked the germ of an experiment. Could I walk a mile in those shoes and not suffer?

Podiatrist Dr. Marisha Stawiski was skeptical. Stawiski points to three small studies that conclude heels, in particular, can create many hip, knee, and other lower-extremity issues. “In the foot alone,” she says, “there are many problems that include but are not limited to Plantar fasciitis, Achilles tendonitis, Haglund’s deformity, painful corns and calluses, Metatarsalgia, Hallux limitus, and Neuromas.”

She admits that some of the technology available, like memory foam and built-in arch support, can diminish components of the problems associated with heels, but the fact that all high heels are thrusting the foot into a very unnatural position for a prolonged period of time is the biggest issue. “Technology cannot change the foot kinematics of someone who wears high heels,” Stawiski says. “I try to practice what I preach and stay away from really high heels almost all of the time, and I do not recommend high heels to my patients.”


I remained undaunted. I found five brands that claim to be designed specifically to provide comfort even though the heel height hovered around three inches. I also reviewed a standard pair by Sarah Jessica Parker for comparison. I put each pair through the rigorous pace of spending a full day walking, standing, and sitting. On those days, I walked at least a mile outdoors and made countless laps around the office. Here’s what I discovered:

[Photo: courtesy of Ally]

Little Black Heel

Ally Shoes, $285

These were the first pair I tried with the help of founder and CEO Samantha Dong. In a small conference room inside Luminary’s collaboration space, Dong urged me to try several pairs to accommodate my feet. As with many humans, one of my feet is slightly larger than the other. And through my years of dancing (and my genetic predisposition for bunions) I discovered that my narrow feet actually fit better in a wider shoe.


Dong understood this as she herself couldn’t find shoes to fit after suffering a foot injury. Her heels were crafted in collaboration with designer Sara Jaramillo and podiatry expert Dr. Roxann Clarke. I especially loved Ally’s suede interior that is fitted with a pad that goes under the toes to make sure they’re cushioned, as well as the slightly curved heel that was reminiscent of the female office denizens in Mad Men.

The minute I slipped on the correct fitting pair, I started striding around, surprised by the ease with which my foot struck the smooth concrete floors. I wore them outside immediately, taking off for an appointment many blocks away. They remained comfortable throughout the walk, and for the standing I did after. I wore them home, taking them off only after I’d arrived. My insteps were a tad bit sore but recovered quickly. I would have donned them again the next day, but I had to try a different pair. Sacrifices, people.


Grand Ambition

Cole Haan, $190

One of the most comfortable pairs of shoes I own are a pair of flat Cole Haan wingtips, so I had high hopes for these. The representatives at Cole Haan told me they were just releasing a new line called Grand Ambition that was designed with the help of the University of Massachusetts at Amherst’s Biomechanics Laboratory for “uncompromised fit, feel, flexibility, and cushioning.”

Once again, I started the day with them, even though the “jaguar print” calf hair isn’t a style I’d choose myself. I did love the little line of gold that lined the exterior tip of the toe. I received a lot of compliments as I made my way through the office, in and out of meetings, and running errands. The mile walk wasn’t supremely comfortable, but it was way better than with traditional heels. I was very pleased not to have to shorten my stride in the way that I tend to do in a standard pair of heels.


The standout feature was how quiet these shoes were. The sole is thicker than normal and has treads, so my footfalls on the polished concrete floors of the office were muffled, something I appreciated in a quiet office environment.

[Photo: courtesy of Marion Parke]

Mara Suede Pointy Toe Ankle Strap Pump With Scalloped Edge

Marion Parke, $650

I was unabashedly elated when I pulled these delicate shoes from their protective bag. I’ve always been a sucker for an ankle strap, and these, though slightly higher than three inches, promised stability. The eponymous brand was designed by a former podiatric surgeon who doesn’t believe people should have to suffer to wear heels.


The shoes have a contoured insole “sculpted to follow the natural contour of the bottom of the foot.” Marion Parke also built in arch support and cupping in the heel and added material along the outside to encourage a more stable position of the foot. That said, the slender heel wasn’t quite as stable as I’d have preferred, especially as I walked around the city.

The hazard in high heels is always that you could step into cracks in the sidewalk. I didn’t, but I found myself tiptoeing around any potential divots, which forced the small muscles in my ankles and feet into overdrive. I would certainly be happy to wear them again, maybe not for quite an entire day of running around. I often speak at conferences, so I’ll definitely be reaching for them when I have to be onstage. You simply can’t beat the look of these delicate stilettos.

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Classic Black Mile-Marker Heels

Betabrand, $128

I’ve been covering Betabrand nearly since its launch as a menswear brand. Over the years, the company has expanded into women’s clothing, and its designers have taken some of their cues from customer crowdsourcing.

These were the most lightweight of the shoes I tried, thanks to the air mesh upper and an outsole of thermoplastic rubber. Inside, they are fully lined with memory foam and have a stabilizing insert to keep your feet from sliding. The heel is slightly lower than three inches, which should have made them even more easy to walk in. Unfortunately, my particular foot issues (hello bunions!) rendered the fit around the instep a bit too snug. I wore them for the full day anyway, and though my bones were stinging, my insteps were just fine. For those of you with healthy feet, the Mile Markers may just be a game changer.


Victoria High Heel 2.0

Antonia Saint, $265

This was the only brand that actually put me through a series of measurements before even letting me try on a pair. My feet were measured for length, width, and circumference, and surprise! I was offered a pair that was a half size larger and wider than my regular size.


Founder Antonia Dunbar clucked over the state of my feet and recommended I not step out immediately in the heat and try to walk on her 3.5-inch heels, even though the footbed was designed to feel like a sneaker (and it did). Nevertheless, I had an appointment a little over a mile away from her studio space in Long Island City. Along the way, I ran into a friend, so I was standing and talking for a while before walking. It was over 85 degrees that afternoon, and my determination petered out around the half-mile mark. I did take them off to switch to flats but not before appreciating the ballistic nylon heel, which won’t tear, even if it gets caught on the pavement.

I wore them again in the office to complete my mission. In air-conditioned comfort they did, indeed, feel like athletic shoes. If you want a sky-high heel that is kind to your insteps as you stand essentially on tip-toe, these are your best bet.


Comparison heel: Carrie T-strap

SJP Shoes, $355

I couldn’t resist trying Sarah Jessica Parker’s eponymous brand as my “traditional” high heel for comparison. Images of her famous Sex in the City character (which this style was named after) danced in my head while I strapped on these delicate pumps. I practically pranced out of their office and out into the Flatiron district expecting a vehicle to pass and splash me with bilge water, just like Carrie’s opening-credit mishap.

Fortunately, that didn’t happen, and I proceeded to walk the mile in this T-strap pump with its wickedly sharp heel. The recommendation for sizing of this style was a half-size down, but I actually had to get a full size up because they are narrow and pointy. They aren’t made to do that much walking, but I sure was delighted every time I looked down at my feet during the day. I felt pretty—and I’d make the sacrifice again, with pleasure.


Bottom line

Each of these brands offers a comfortable upgrade to the standard high heel. My favorites were Ally and Antonia Saint because they worked well with the shape of my feet. Your mileage may vary, of course.

Those of you devoted to designer shoes won’t suffer the sticker shock I had at some of these prices. But seeing how intricately crafted each was, with thoughtful details not even found on some luxury brands, I couldn’t help but wonder: Aren’t my feet worth it? As Antonia Dunbar confessed in a conspiratorial whisper, “When your feet hurt, you’re miserable.” And when you’re miserable, you can’t be productive at work, no matter how good you look.


About the author

Lydia Dishman is a staff editor for Fast Company's Work Life section. She has written for CBS Moneywatch, Fortune, The Guardian, Popular Science, and the New York Times, among others.


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