In our opinion, there is no such thing as too much comfy-shoe content. Sneakers, of course, can make for both comfortable and nice-looking footwear, but things get a little trickier from there as there’s a fine line between fugly and just plain ugly. So to find the best comfy and not-offensive-looking shoes out there, we asked 21 cool women who spend most of the day on their feet — including servers, chefs, nurses, flight attendants, hairstylists, protesters, photographers, real-estate agents, and cleaners — about the shoes they wear. Their answers range from Shark Tank–approved high heels to classic Crocs to ’90s-style mary janes. Plus a few hacks for making your cute but ill-fitting shoes more bearable.
We admit that some of their picks aren’t the most stylish or trendy, but remember that the now-fugly-cool Dansko clog was around long before it became the official shoe of hipster ceramists. So who can really say what’s next? All we know is that if you’re dreaming of a future with blister-free feet and a pain-free back, you will find the footwear — including heels, flats, clogs, boots, and sneakers — to help you achieve that on the list below.
Best comfortable heels
“I’m telling you, anything, literally anything from Clarks that I’ve put on my feet, I’m like, Oh, yeah. I’m willing to pay more for them because I know that they’ll be comfortable,” says Cassadi Currier, a hairstylist at Pembly Joon. (She’s not alone: They’re an overwhelming favorite among our experts — three recommend the brand.) And according to Currier, these heels (not wedges) are her go-tos because they keep her feet comfortable for about four to six hours. Currier appreciates Clarks because they come in a variety of styles, including these “relatively cute” ones, rather than the “kind-of-grandma heels” or wedges. The Kaylins are a particular favorite because they “look like booties, but they have a sandal for your toes to show through,” she explains.
According to flight attendant Crystal Roseberry, women in her field “typically wear two pairs of shoes at work.” There are terminal shoes, which tend to be sexy heels worn from the time flight attendants arrive at the airport until they’re in the air, and there are in-flight shoes, which tend to be frumpy but comfy. But Roseberry says these mary janes from Clarks — of which she has multiple pairs — are “the best of both worlds — comfortable enough to wear all day long and still fairly cute.” They’re her “hands-down favorite,” she says. Sandra Hinton, who has been a flight attendant for 42 years, says these shoes are extremely comfortable thanks to the “rounded toe, cushion, and some support in your instep” as well as “a little bit of platform and a low heel.”
“I find the pickings to be kind of slim when looking for something supportive that still looks young and cool,” says server Tess Parker. Dansko’s Ankle-Strap Clogs, which Parker calls “a solid-gold tip” for anyone with knee or back problems, are the first pair of shoes she has found that fulfilled her requirements of being both supportive and cool-looking. The clogs have a “slight but forgiving platform” that helps make them so comfortable, according to Parker, who adds, “Our jobs tend to destroy shoes, but these are really long-lasting.”
When showing apartments, Realtor Madison Sutton, a.k.a. “the NYC Agent” on TikTok, easily hits 20,000 steps per day, traversing about 60 flights of sometimes-rickety stairs. Because her job requires her to be professional during appointments but nimble as she commutes between them, she’s a fan of these futuristic heels from Shark Tank alum Haley Pavone, which convert into flats in less than 30 seconds. “I can do it while standing up, which is kind of cool,” she says. You just click the heel, she explains, “and it pops right off.” And we know what you’re thinking, but no: “They come with a dust bag, so you’re not putting the dirty part of your shoe back in your purse.”
Best comfortable flats
Nurse Sorah Edeltuch told us she spends most of her days in sneakers. But for something a little more polished, Edeltuch puts on the Easy Spirit Getcity flats, which she says are just as comfortable. “Easy Spirit mostly makes grandma shoes, but this is the one pair that doesn’t look like it’s for grandmas,” she says. “They feel like you’re walking on supportive pillows. I get so many compliments when I wear them to work.” Easy Spirit no longer sells the Getcity flats, but they’re built on the same base as these Gessica Ballet Flats, which are available for $70.
“I’ve been through so many flats,” says flight attendant Heather Kovarik. And after testing out many styles that didn’t do the job, she finally landed on two trusty pairs from Dr. Scholl’s and Fila. “Their soles have traction, so you’re less likely to slip, and they have a fair amount of cushion on the inside,” Kovarik says of both, though she admits that nothing is entirely comfortable after an 18-hour day. But “these two shoes help the most” of all the ones she’s tried.
Flight attendant Roseberry’s favorite comfy flats are this pair from Clarks, which she says are “well made and cute, provide good support, and last forever.” She wears them during long shifts in the air and says they keep her feet “feeling good all day.”
Best comfortable clogs
Merica Lee, denim designer and maîtresse d’ at Frenchette, spends a lot of time running between her factory in Brooklyn, the Garment District in Manhattan, and the restaurant in Tribeca. That’s why she looks for shoes that allow her to “easily bop around between boroughs but are cute enough to wear to work.” She calls Dankso clogs “a standard for restaurant folks,” as well as “one of the most comfortable pair of shoes you can own.” Lee opts for an all-white pair, which she says feels more stylish and unexpected than the classic black. “From running around the city all morning to standing for eight hours straight behind the host stand, I have absolutely no problems wearing them all day.” Flannery Klette-Kolton and Lauren Gerrie, who spend a lot of their time standing in commercial kitchens as the co-founders of catering company Big Little Get Together, also love Dansko clogs. And author Stephanie Danler told us she’s been wearing her “clunky but kitschy” Dansko clogs since since she got her first restaurant job at 15.
Il Buco Alimentari chef de cuisine Jamie Hogg’s “go-to shoe” is a simple pair of Birkenstock Birki shoes. “They’re nonslip, low-key, last at least two years, and have a changeable inner sole,” so when you wear them down, you can swap in a new comfy sole instead of buying a second pair.
They aren’t the most stylish pair on this list, but for an even more affordable — and just as comfortable — clog, Crocs will do the trick. Chloe Coscarelli, founder of the restaurant chain By Chloe, wears them while cooking at work and at home because “they’re really comfortable and have the right amount of elevation to promote good posture.”
If you want to lean further into the Croc aesthetic and experiment with the brand’s trademark colorways and patterns, Lily Marotta — comedian, cleaner, and co-host of the podcast Celebrity Book Club — says this camo pair “changed my life, especially at work,” after she bought them at an outlet mall last year. “After a long-ass day of cleaning, my legs are sore, my back hurts — but when Crocs entered the picture, not only am I way less sore, but they make the style transition from bathroom scrubbing to the club seamlessly,” she explains. And yes, they’re Jibbitz-compatible.
Photographer Rochelle Brock is a fan of Crocs, too, specifically the Platform Clog, which is “a bit harder and more structured,” she says. “The whole shoe is rubber, and they slip right on and off, which is perfect for when I’m in the studio setting up or getting some work done.” The platforms come in all the fun colors you expect from Crocs; Brock customizes hers with charms.
Best comfortable boots
“I feel like boots, no matter what kind of boots you buy, you have to break them in; it’s like a wear period of at least a couple weeks to a month before you’re like, Okay, these are my boots,” says Currier. Of all the boots she recommends, she says these are the quickest and easiest to break in. On top of that, she finds them to be stylish. “Being a hairstylist, I have to look presentable and I have to look like I know something about the fashion world,” Currier says, so she tries “to find shoes that are at least ranking a level 7 out of 10 that I can wear and be comfortable in and still look cute.”
For winters in New York City, Gerrie swears by Dr. Martens Chelsea Boots as a comfortable but effective way to navigate icy streets. Lee — who wears a platform pair — agrees: “I can stomp around the factory floor in them by day, but the style means they’re cute enough to wear to Frenchette at night.” Since Dr. Martens were originally designed as workwear, they’re “really supportive and last forever,” Lee explains. And the air-cushioned sole is so supportive, “you’ll never want to take them off,” she promises. The infamously tough leather might take a month or two to wear in, but it ends up being worth the effort. Treehouse Social Club hairstylist Jikaiah says that while her colleagues are devoted to Danskos and Crocs, she has found the ankle support Docs provide to be crucial for long days on the job. “I’ve had the same classic black pair for two years, and I just bought a brown pair as well.”
Currier loves combat-style boots like these lace-up Dr. Martens. She says the air-cushioned sole is super-comfortable, and she appreciates that they’re slip-resistant. “When I’m ringing my clients’ hair out, there’s water on the floor,” she explains. “Having done this for a while, I’ll know not to slip in it, but it’s nice to know that if I want to walk through it quickly, or if I have to, I’m not gonna fall and die.”
Chef Adina Halpern relies on Blundstone boots because they’re “very resilient” and “can transition from the kitchen to my regular life.” They’re waterproof, slip-resistant, and offer more ankle support than clogs or slides, which is a must in a busy commercial kitchen. Halpern even put their slip resistance to the test when she walked “around a butcher shop where the floor was completely covered in beef fat and never slipped.” Plus these have sheepskin lining that provides extra comfort and coziness during long stints of standing.
“Not only are they super-durable but the soft leather makes them very comfortable when I’m on my feet for hours,” Helene Henderson, the founder of the Malibu Farm restaurants, says of the Frye Veronica Combat Boots. Beyond feeling good, these are extremely versatile and easy to pair with work or weekend outfits.
“Sometimes I work 14 hours on my feet, so I need to be comfortable, but I also want to look nice and cool all at the same time,” says Chelsey Pickthorn, master stylist and founder of Pickthorn Salon. When the weather cools, her preferred way to keep her feet comfy but looking nice is by pulling on these Red Wing boots. “They are the most sturdy and soft and comfortable work boot.” Pickthorn loves them so much, she has her eye on a second pair in brown.
If the Red Wing boots are a little out of your price range, Currier recommends Thursday boots as an alternative. Currier’s boyfriend introduced her to the brand, which are “very similar to Red Wing as far as quality goes, but they’re at a more consumer-friendly price.” This combat-stye pair features patent leather on the outside as well as a full leather lining and shock-absorbing insoles for extra comfort.
Sutton is such a fan of Schutz that she buys around “eight pairs of shoes a year” from the brand, saying they’re “really well made” and last her a couple of seasons on average — “which is insane in New York.” The platform booties she prefers are a little pricey, so she says it’s worth waiting for deals. “They’ll often do sales where they’re 50 percent off, especially in the off-season.”
Best comfortable sneakers
As a photographer, Erin Patrice O’Brien sometimes spends 15 hours straight on her feet during a shoot. “It’s important to be able to get into really small places, climb down on the floor, or carry stuff for long periods of time, so with all those things, the last thing that you want to have to worry about is if your feet are gonna hurt.” That’s not the case with these Cruzv1s. Although she doesn’t love the look of the shoes, she has been focused on comfort over style ever since she had to deal with plantar fasciitis five years ago. These shoes have New Balance’s Fresh Foam cushioning in the midsole, which she says makes all the difference. “Once I wore the memory foam, I couldn’t go back to hard shoes or other brands.” Within the New Balance line, she thinks these are the standout. “I tried them all on at Macy’s in Downtown Brooklyn, and these were the most comfortable.” And even though these are super-comfy, she still slips Dr. Scholl’s inserts into all her shoes for extra support.
Air Force 1s are a favorite among Gen-Zers and make a great gift for the teenage girl in your life. Three grown women have told us it’s their favorite white sneaker as well. The universality of the AF1s’ comfort is debatable, but Strategist writer Chloe Anello swears by them — especially for her tricky-to-shop-for feet. “I have really big feet, so with a lot of shoes, the arch is in the wrong spot, and they’re not comfortable,” she explains. “Air Force 1s I can wear all day every day and not have an issue. I’ve worn them on six-mile walks before, and they’ve been as comfortable as my APL running sneakers.”
These may seem like a trendy dad shoe, but Strategist writer Tembe Denton-Hurst says they’re classics. “For a DMV girl like me, New Balances are a rite of passage,” she says. “They’re a staple basic shoe, like what AF1s are to NYC.” Plus, she says, they’re “stupidly comfortable.” She has worn them for 12 hours at a time and worked out in them without complaint. And while they might not necessarily match with everything, they’re so comfortable that she tries to make it work. “I toss them on with jeans, biker shorts, and dresses — they’re stylish in a normcore sort of way and remind everyone that the pandemic has turned me into a comfy-footwear evangelist,” she says. “They make everything more pleasant and are the one shoe I absolutely have to have with me no matter where I go.”
Brock describes her style as sporty and girly and says sneakers are her go-to shoe style. She looks for options that support a wider foot, look good, and can be dressed up or down depending on the assignment. These chunky Filas, which she has in a stylish pink floral pattern only available on resale sites, are great for working long hours. “They truly feel like you are walking on a cloud.” Plus they slip on and off easily, which she says made them great for travel pre-pandemic. “I’ve traveled from New York to England and Egypt with them.”
“The Ultraboosts are a really good Adidas sneaker for everyday wear,” Currier says. “They’re super-comfortable, easy to put on, and they go with a lot of different things because they come in so many different colors.” These are specifically designed for running, a key factor for Brittany Libman, who used to be on her feet ten hours at a time as an Amazon warehouse employee. “I always prefer to wear shoes that are specifically made for activewear, like running shoes,” she says. “My shoes were the Adidas running-style sneakers, because it was the most comfortable but also nonslip,” which she needed while working on hard floors near lots of machinery.
Both Gerrie and bartender and seamstress Pam Wiznitzer say Converse’s Chuck Taylor All Star sneakers (a favorite among Strategist staffers) are as comfortable as they are classic. “With additional cushioning inside, elastic by the tongue, laces (to keep the fit snug), and better gripping on the floor, these have become my new work shoe and also ones that I can walk all around New York City in,” explains Wiznitzer, who prefers low-tops. Gerrie — who gravitates toward high-tops in either canvas or leather — agrees, calling her Converse her “most tried-and-true shoe.” Brock likes the high-tops as well, especially for her wider feet. “They are extremely comfortable when I have to do a lot of walking or standing for a longer period,” she says. “I have some in a few different colors, and I’m able to change my look with them and still be stylish and cute on set.”
If your feet are too wide for Converse like Currier’s or you generally have trouble finding tennis-style sneakers, she recommends these Clarks. Her wide feet slip right into them, and they have the added benefit of being leather, “which is nice because you can just wipe them off,” she says. “For me, doing hair color all day, if I get something on my shoes, I’m devastated, so it’s nice to be able to do a quick wipe and not worry about it.”
“Cushion and arch support are major keys,” says Nina Sarhan, a Washington, D.C.–based organizer and protester who sometimes walks for hours during protests. “I walked 13 miles on 395 a few weeks ago with a group of Black Lives Matter protesters, shutting down a major highway for a few hours. I probably walked for six hours that night starting at five and ending around midnight,” all in these platform Keds. “I find that it really offers extra support and cushion especially for long walks,” Sarhan says of the platform. “Keds also have sturdy construction, so they’re great for miles on the roads back and forth through Washington, D.C.” She thinks the rubber soles help absorb the shock of each step, and they keep her going in inclement weather. “Rain doesn’t stop the protests, so I need the shoes I wear to not weigh down or get gross in the rain,” she explains. “And they need to have traction so I don’t slip on crosswalks where the road can get slippery in the rain.”
According to Yuki Izumi, Hi-Collar café’s manager and signature barista, Nike makes the most comfortable sneakers to wear while slinging drinks behind the counter, owing to their supportive arches and snug fit. Although they are athletic sneakers, her favorite Roshe Ones look a little less so than other gym shoes.
When she’s not wearing clogs or boots, Lee relies on her “sleek and modern-looking” Nike Air Max 270s, which she says feel like walking around on “sponges.” She tells us they look good with everything from jeans and jumpsuits to dresses and trousers, “but most important, they feel good.”
As a professional ballet dancer, Erica Lall pays extra attention to taking care of her feet. “I have to be careful with what shoes I wear because I obviously use my feet for everything,” she says. These Nikes have been her go-tos for years. “I wear them every day and won’t stop wearing them until I’ve worn them out. Before COVID, I walked around Europe in a pair with my friend. We walked miles and miles every day, and they really held up.” She says the shoes have never given her a blister, and they support her arches, “which is a necessity for ballet dancers.”
Sutton is “very into” Naked Wolfe’s range of platform shoes, which range from “very Bratz” heels and pumps to these chunky, comfy tennis sneakers. She’s about to order her third pair, saying the platforms are “more even” than other brands and have an incredibly long lifespan considering the tough New York City pavement she’s pounding every day.
Best comfortable sandals
O’Brien found OOfos sandals in a Google search for the best shoes for people with plantar fasciitis, and they’ve become her go-to shoes for summer. “Those are super-comfortable, and they’re aerodynamic for the feet,” she says. They have a foam base, just like her favorite New Balance sneakers, and the OOfoam is said to absorb 37 percent more impact than traditional footwear does.
While Gerrie got her start working in professional kitchens, she now spends a lot of time cooking on sailing boats and at yoga retreats in more tropical locations. If you’re looking for comfy footwear for warmer weather, she swears by Teva’s Universal Sandals, telling us they not only feel good but are super-cute and waterproof to boot. The brand is a favorite of actress Sasheer Zamata, who included the wedge version of the Universal Sandal on her list of things she can’t live without. “I feel like I can walk forever in them,” she said. Strategist editor Anthony Rotunno loves Tevas, too; he is such a fan, he recently became the proud owner of a third pair. The Universal Sandal also came recommended by trail guides when we asked them about the best hiking sandals (which by default need to be comfortable enough to get you through whatever trek you’re on).
Gerrie told us she loves Birkenstock Arizona EVA Sandals — another Strategist-approved shoe — as a comfy warm-weather option. Sarhan, jewelry designer Irene Neuwirth and stylist Karla Welch swear by this style, too, and writer Alison Freer loves its ecofriendly EVA material, which she says is “both light on your feet and a dream to pack for travel.”
For a sportier-looking sandal, Pickthorn suggests this pair from Eileen Fisher, which she says are “incredibly sturdy for walking and working” because of their thick straps and springy platform.
Currier loves a chunky sandal in the summertime. “I’m 100 percent a firm believer that a platform takes the pressure off of your knees,” she says, and the platforms on these suede sandals from Clarks come in at about two inches tall.
Even though these sandals have more straps than the other sandals on our list, Currier thinks these Dr. Martens “are even slightly more comfortable than the Clarks.” They have the same squishy sole as the Dr. Martens boots she picked above and are made out of vegan leather so “they stretch out pretty nicely.”
Best comfortable socks and liners
A common misconception about comfy footwear, Sutton says, is that high heels, fast-fashion finds, and fussy designer brands are a no-go. But she has found that the right pair of padded socks can go a long way toward reducing pavement impact and redistributing weight while walking. Adding these Milano ballerina socks to a cheap pair of Amazon sandals? “It literally transformed a $30 pair of shoes into $80 shoes in quality.” And the no-show design of Relaxife’s liner socks means you can wear them with your open-toed heels while the balls, arches, and heels of your feet secretly relax into the padding. “It completely blends in, and they come in all different skin tones as well as a traditional jet-black sock.”
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