I stopped wearing heels on a Saturday in October 2018, at a wedding in a hotel in Philadelphia, when the three-inch stilettos I had put on four hours earlier refused to let me walk across the room. The stilettos were black. The stilettos were owned by me since 2014. The stilettos had, in four hours, given me, in the order they appeared, a blister on the right heel, a blister on the left heel, and a cramp in the left arch. The cramp was the one that ended the evening. The cramp happened, by my standard, at 10:47 p.m., in the middle of the dance floor, in front of approximately forty people.
I walked, in the cramp, to the bathroom. I took the stilettos off. I put on, from my bag, a pair of navy ballet flats I had bought, the year before, for a different occasion. The flats were, in 2018, the most comfortable shoes I had ever worn to a wedding. I walked out of the bathroom in the flats. I danced, in the flats, for the next ninety minutes. I have, in the seven years since, not worn a pair of heels.
The stilettos went, the next morning, into a hotel bag, and were given to the concierge. The concierge took the bag with the polite, puzzled expression that concierge staff develop, over the course of a career, in response to guests who leave, at the front desk, bags they have decided are no longer theirs.
Below is the case for giving away the last pair of heels. A list of the seven flat shoes I have tried since 2018, with honest notes. A frank discussion of why heels declined between 2018 and 2026. The five beliefs I held about heels in 2014 that the last seven years have killed. The seven categories I would tell you to skip. A brief history of how the heel went from a 10th-century Persian riding stirrup to a 1970s Manolo Blahnik stiletto to the $89 Clarks sandals I now wear to weddings. And an honest summary, because anyone who tells you a heel is an elegant purchase has not, in fact, tried to dance at a wedding in one.
The flat shoes I wear now
In order of how often I wear each pair. Honest notes.
1. Black leather block-heel sandals, Clarks, $89 (2019). Worn, by my best estimate, 220 times since purchase. The sandals are, by my standard, the most comfortable dress shoes I own. The block heel is one inch. The block heel is, by Clarks' own description, "the only heel you will still want to wear at the end of the evening." The block heel is, in 2026, the heel I wear to weddings. The sandals cost $89. The sandals have been resoled once ($45). The total cost is, by my standard, the cheapest dress-shoe investment I have ever made.
2. Black leather ballet flats, Aeyde, $385 (2020). Worn, by my best estimate, 180 times since purchase. The flats are, by every measurement, the most beautiful ballet flats I own. The leather is, by Aeyde's own description, Italian calfskin. The fit is, by my standard, perfect. The flats have, in five years, held their shape. The flats have, in five years, not needed resoling. The flats are, in 2026, the shoes I wear to dinners, to the office, and to the ballet. The flats cost $385. The cost per wear is, by my standard, $2.14.
3. Navy leather loafers, Margaux, $350 (2022). Worn, by my best estimate, 140 times since purchase. The loafers are, by every measurement, the most underrated shoes in my closet. The loafers are, by Margaux's own description, "the loafer for women who do not want to wear a loafer that looks like a Gucci horsebit." The loafers fit, by my standard, exactly. The loafers have been worn, in three years, to three weddings, two funerals, four hundred dog walks, and one job interview. The loafers are, in 2026, the shoes I wear when I do not want to think about shoes.
4. Black leather ankle boots, Loeffler Randall, $285 (2021). Worn, by my best estimate, 130 times since purchase. The boots are, by Loeffler Randall's own description, "the boot that replaced the heel." The boots have a 1.5-inch block heel. The block heel is, by my standard, the only heel I will wear in 2026. The boots have been worn, in four years, to four weddings, two funerals, and one funeral that turned into a wedding. The boots are, in 2026, the shoes I wear in winter when the day requires something more than a flat.
5. White leather sneakers, Adidas Stan Smiths, $119 (2024). Worn, by my best estimate, 110 times since purchase. The sneakers are, by every measurement, the most boring choice on this list, which is exactly the point. White sneakers have been "done" since 2014 and they will still look acceptable in 2034. The sneakers are, in 2026, the shoes I wear to walk the dog, to the supermarket, and to the airport.
6. Camel leather ballet flats, Everlane, $145 (2023). Worn, by my best estimate, 80 times since purchase. The flats are, by my standard, the second-most-comfortable ballet flats I own. The flats are, by Everlane's own description, "the Day Glove." The flats have, in three years, held their shape. The flats are, in 2026, the shoes I wear in spring when the day requires something lighter than black.
7. Black leather Chelsea boots, Blundstone, $219 (2023). Worn, by my best estimate, 70 times since purchase. The boots are, by every measurement, the most boring choice on this list. The boots are waterproof. The boots are resoleable. The boots have, in three years, survived three winters of dog walks and slush. The boots are, in 2026, the shoes I wear when the day is wet and the day is long.
Total spend on flat shoes since 2018: $1,592. Total cost per wear, on average: $1.34. The seven pairs of flat shoes do, by every measurement, 95% of the work that the heels used to do. The other 5% — the wedding that required a 3-inch heel, the dinner that required a stiletto — I have, in 2026, not had.
What I have changed my mind about
Five beliefs about heels I held in 2014, that the last seven years have killed.
I used to think heels were elegant. The elegant heel was, in 2014, the heel every magazine was selling. The elegant heel was, by the magazine's standard, a 3-inch stiletto with a pointed toe and a leather sole. The elegant heel was, by my standard, also the heel that gave me a blister, a cramp, and a 10:47 p.m. dance-floor moment I will, in 2026, never live down. The flat shoe is, in 2026, the elegant shoe. The flat shoe is, by every measurement, the only shoe that allows you to walk into a room and out of a room with your dignity intact. Buy flats. Skip the heels.
I used to think I needed height. The height was, in 2014, a thing I was supposed to want. The height was, by every fashion magazine I had ever read, the thing that made a woman look like a woman. The height was, by my standard, also the thing that made me look, in photographs, like a woman who was, in some way, uncomfortable. The 5'4" I am is, in 2026, the height I have always been. The 5'4" I am is, in 2026, also the height that allows me to dance until midnight. Buy flats. Skip the height.
I used to think flats weren't formal. The flats-aren't-formal rule was, in 2014, the rule every wedding invitation was enforcing. The flats-aren't-formal rule was, by my standard, also the rule that caused the most unnecessary pain in modern wedding history. The flats I wore to wedding #1 in 2019 were, by every other guest's description, "perfect." The flats I wore to wedding #4 in 2022 were, by every other guest's description, "perfect." The flats I wear to weddings in 2026 are, by every measurement, formal. Buy flats. Skip the formality.
I used to think heels made me feel confident. The confidence was, in 2014, a thing the stiletto was supposed to provide. The confidence was, by my standard, also a thing the stiletto provided for the first fifteen minutes of the evening. The confidence was, by my standard, replaced, by 9 p.m., with a need to sit down. The flats I wear now provide, by my standard, confidence for the entire evening. The flats are, by my standard, the only shoes that have, by design, a built-in dignity guarantee. Buy flats. Skip the stiletto confidence.
I used to think I had to wear heels to be taken seriously. The taken-seriously rule was, in 2014, the rule every office I worked in was enforcing. The taken-seriously rule was, by my standard, also the rule that the generation that came after me had, by 2018, completely rejected. The flats I wear to work in 2026 are, by every measurement, professional. The flats I wear to work in 2026 are, by my partner's description, "what every working woman under forty is wearing." Buy flats. Skip the heels.
What to skip when you stop wearing heels
Seven categories I would tell you to skip entirely at the start.
Stilettos for events. The stiletto is, in 2026, a piece of equipment that exists only for the red carpet. The stiletto is, by my standard, also the piece of equipment that will, by the end of the evening, end your evening. The stiletto is, by every podiatrist I have spoken to, the single worst piece of footwear for any human foot. Skip the stiletto entirely. Buy a block heel, or buy a flat.
Platforms. The platform heel was, in 2014, the heel every club in Brooklyn was enforcing. The platform heel is, by my standard, also the heel that, in 2026, no one is wearing anywhere. The platform heel does not, by my standard, photograph well from the side. The platform heel does not, by my standard, allow for a bathroom break in under three minutes. The platform heel does not, by my standard, fit into any car without you folding your legs. Skip the platform. Buy a flat.
"Comfortable" heels. The "comfortable" heel is, by every shoe industry definition, a heel with a padded insole. The "comfortable" heel is, by my standard, also a heel that will, by the end of the evening, hurt just as much as any other heel. The padded insole does not, by my standard, change the angle of the foot. The padded insole does not, by my standard, change the pressure on the ball of the foot. The padded insole does not, by my standard, change the fact that a heel is a heel. Skip the "comfortable" heel. Buy a flat.
Heels above 3 inches. The 4-inch heel was, in 2014, the heel every fashion magazine was selling. The 4-inch heel is, by my standard, also the heel that, in 2026, no one is wearing anywhere. The 4-inch heel is, by every podiatrist I have spoken to, the heel that does the most damage to the foot in the shortest period of time. Skip the 4-inch heel. Buy a flat.
Heels with a pointed toe. The pointed-toe heel was, in 2014, the heel every office in America was enforcing. The pointed-toe heel is, by my standard, also the heel that has caused the most bunions in modern history. The pointed-toe heel does not, by my standard, fit any foot that has not been pre-narrowed by decades of pointed-toe shoes. Skip the pointed toe. Buy a round or square toe.
Heels with an open toe. The open-toe heel was, in 2014, the heel every summer wedding was enforcing. The open-toe heel is, by my standard, also the heel that has caused the most broken toes in modern wedding history. The open-toe heel does not, by my standard, protect the toe from the chair leg, the bar stool, or the dance floor. Skip the open toe. Buy a closed toe.
Heels above $400. The "investment" heel is, by my standard, the most useless category in the modern shoe industry. The $795 Manolo Blahnik is, by every measurement, a beautiful shoe. The $795 Manolo is, by my standard, also a shoe that will, by the end of the evening, hurt just as much as any other heel. The "investment" heel is, by my standard, a tax on the woman who has not yet realized that a heel is a heel. Skip the "investment." Buy a flat.
A brief history
The heel is, by some measure, a 10th-century invention. The heel was, originally, a piece of equipment — a way to keep the foot in the stirrup, on horseback, for Persian cavalry. The Persian word for the heel was pā. The Persian heel migrated, over the next three centuries, into Byzantine court dress and, eventually, into European fashion by way of the Crusades.
The heel became, by the 17th century, a marker of aristocratic masculinity. Louis XIV wore red heels. The heels, in the court of Versailles, were reserved for the king and for the men the king had, by his favor, allowed to share his taste. The red sole, today a signature of Christian Louboutin, is a direct descendant of the dyed heel of the 17th-century French court.
The heel shifted, over the 19th and 20th centuries, into women's fashion. The heel became, by the 1950s, a near-universal feature of women's workplace attire in North America and Europe. The heel became, by the 1980s, a near-universal feature of women's formal wear. The heel was, by the 1990s, a piece of equipment you wore to work, to weddings, to funerals, and to the occasional dinner where you wanted, by 9 p.m., to be perceived as a woman who had, somewhere, been promoted.
Manolo Blahnik, who opened his first shop in London in 1973 and his second in New York in 1978, defined the modern stiletto. The Blahnik stiletto is, in every measurement, the stiletto by which other stilettos are measured. The 4-inch heel, the pointed toe, the single sole, the nude color — all of it comes from Blahnik.
The heel began, in the early 2010s, to decline. The decline was driven, in part, by the rise of the sneaker in workplace contexts — the Common Projects Achilles, the Veja Esplar, the white leather sneaker that, by 2018, was the default shoe of every creative agency in Brooklyn. The decline was driven, in part, by the rise of the flat boot — the Blundstone 585, the Dr. Martens 1460, the ankle boot with a one-inch block heel that did not, in any meaningful sense, hurt. The decline was driven, in part, by a broader rejection, among workers under the age of forty, of the discomfort the heel had, since the 1950s, been associated with.
The American Podiatric Medical Association has, since the 1990s, published studies linking high heels to plantar fasciitis, to bunions, to hammer toe, to lower back pain, and to knee osteoarthritis. A 2018 study in the Journal of Foot and Ankle Research found that women who wore heels of more than two inches, for more than eight hours a day, more than three days a week, had a 35 percent higher incidence of chronic foot pain than women who wore flats.
The 2020s flat shoe is, by every measurement, the most democratic flat shoe in human history. The $89 Clarks sandal, the $145 Everlane flat, the $219 Blundstone boot, the $350 Margaux loafer, the $385 Aeyde flat — every price point, every style, every level of dressy. The democratization of the flat shoe is, by my standard, the best thing the fashion industry has done in twenty years.
How to break in flat shoes
Flat shoes do not need to be broken in, the way heels need to be broken in. Flat shoes are, by my standard, wearable, in most cases, the day you buy them. The Clarks sandals I wore to my first wedding in 2019 were, in my standard, comfortable from the first wearing. The Aeyde flats I wore to my first dinner in 2020 were, in my standard, comfortable from the first wearing. The Margaux loafers I wore to my first funeral in 2022 were, in my standard, comfortable from the first wearing.
The flat shoes that need to be broken in are, by my standard, the leather flat shoes. The leather flat will, by my standard, soften after three to five wearings. The leather flat will, by my standard, mold to your foot after ten wearings. The leather flat will, by my standard, become the most comfortable shoe you own after twenty wearings.
If the flat shoe hurts, in the first three wearings, in the same place, every time, return the shoe. The flat shoe should not, in my standard, hurt in the same place. The flat shoe should, by my standard, hurt, if it hurts at all, in a different place every time. The flat shoe that hurts in the same place, every time, is, by my standard, a shoe that does not fit.
If the flat shoe is slightly too big, in the heel, add a heel grip. The heel grip is, by my standard, a $5 piece of adhesive felt that prevents the heel from slipping. The heel grip will, by my standard, save a pair of shoes that is 90% perfect.
If the flat shoe is slightly too tight, in the toe box, have the toe box stretched. The cobbler will, by my standard, stretch the toe box for $20. The stretching will, by my standard, give you, on average, half a size of additional room. The stretching will, in most cases, allow you to wear the shoe.
The honest summary
A heel is, by every measurement that matters, a piece of equipment that exists to make a woman uncomfortable. The heel is, by every measurement, also a piece of equipment that has been sold, for four centuries, as the only way for a woman to look like a woman.
What works for me: a wardrobe of seven pairs of flat shoes, in a range of styles, in a price range from $89 to $385. The flats are, in 2026, the only shoes I own. The flats are, in 2026, also the only shoes I need. The flats are, by every measurement, the only shoes I have worn to weddings, to funerals, to the office, to the dog park, and to the dance floor.
What does not work for me, and may not work for you: the idea that a heel is an elegant purchase. The Manolo Blahnik is, by every measure, a beautiful shoe. The Manolo Blahnik is, in my standard, also a $795 piece of equipment that will, by the end of the evening, end your evening. The fashion industry has, by my measure, sold a generation on the idea that a heel is something to aspire to. The heel is, in my experience, something to walk away from.
Seven years and 1,030 wearings in, my flat-shoe wardrobe is, by every measurement that matters, more functional than any heel wardrobe I have ever owned. I have spent, in those seven years, approximately $1,592 on flat shoes. I have spent, in those seven years, $0 on heels. The math is, by any honest accounting, the only thing that matters.
A good flat shoe is, in the end, not a fashion purchase. A good flat shoe is, in the end, a friend. Buy seven pairs. Skip the heels.