I Asked Stylish People About Their Comfortable Heels

At five-seven, Bria Schirripa, writer of the newsletterFriend Of, doesn’t feel the need to wear heels for the extra height. But this pair gives her “a little something without making me feel like I’m towering over anyone or feeling uncomfortable.” It’s not her first pair, either. She’s worn “the hell out of” other Mango heels, and bought this pair when she was looking for something to wear to the office, out clubbing, and to a wedding. She’s commuted in them several times over the past few weeks, and recently, they went to aNew York Fashion Weekevent followed by a Harry Styles concert at Madison Square Garden. “They withstood a night of dancing and jumping along to everyone’s favorite British pop star,” she says. A friend even asked if they’re Toteme.

Vagabond’s Livia is “a shoe you would want to be caught running errands in,” according toProduce Parties’Sarah Teich. (She recalls someone once complimenting the shoes, saying they were like “Margiela Tabis without the slit.”) They’re “wearable from day one,” and have handled going to a friend’s wedding at a dumpling house in Long Island City, where Teich was caught in an intense rain and wind storm on her way. While they did get soaked, they weren’t destroyed.

On her quest to find “starter heels” — defined as “supportive enough to wear forat leasteight hours (to limit taxi temptation), cost no more than $200, and come in a neutral color (to maximize the number of outfits they’re compatible with)” — writerBella Druckmantried pairs fromEverlane, Franco Sarto, andMadewell. This Vivaia kitten heel ended up being one of her favorites. After some initial rubbing on her toes, they were quickly ready for “modest jogs down subway stairs and comfortable enough to walk multiple miles in.” And the extra-cushioned footbeds make them easier to wear for a full day.

A runner-up in Druckman’s heels search was the Franco Sarto Lyanna slingbacks. “If you’re looking for a pair of heels that you can comfortably wear for a few hours while running down subway stairs, walking across cobblestoned streets, and wandering around the neighborhood,” they’re ideal. It was only at the six-hour mark that Druckman started to feel rubbing on her big-toe knuckle and side of her foot. Be that as it may, “I don’t even feel like I’m wearing heels when they’re on my feet,” she says.

“I love mules with a little heel — always have, always will,” saysYeah It’s Jewelryfounder Chloe Weitman. Her new favorite is the Geneva from Coconuts by Matisse. They didn’t require any breaking in. “I was able to wear them out of the box straight away with no blisters,” she says. Better yet, Weitman can walk around in them for hours at a time. Now, they’re her preferred wedding-guest shoes, partly because there’s nothing precious about them. At a wedding she attended where it was pouring rain, they only “got a little muddy,” while her feet remained clean. The next morning, she could easily wipe them down with water and a paper towel.

“I never understood when I heard people say ‘walkable heels,’” says brand consultantLucia Litman. That is, until she tried the Mabel. Litman can wear it for hours without any toe pinching or hurt soles, even while biking in Amsterdam. Now she doesn’t have to be “the annoying friend that Ubers everywhere because my feet hurt.”

They’re “one of the only platforms with a heel that I can actually wear all day walking the city without my feet hurting,”saysfilmmakerEmily May Jampel. She’s even jumped over slush puddles in them.

“I know it looks like the least comfortable heel,” says Morrigan McCarthy, writer of the newsletterHome Run. But she wore it for her wedding party (where she was on her feet all night) and at “at least eight times since” without getting a single blister. “There was no breaking-in period. They simply didn’t need it,” she says. “The secret is that you jam your foot in that malleable vinyl strapping and they essentially stick to your feet,” she says. The longer you wear them, the tighter they get, which sounds bad, but by 1 a.m., you’ll be thrilled at how jammed in there your feet are.” This also inspires the “confidence to dance, walk many city blocks, and up and down stairs and never worry about them sliding off.” (And while they did remind her ofPleasersinitially, “they have more the visual effect of not wearing a shoe at all.”)

Not only does the platform-heel ofCamper’s Thelma give creative strategistCarrie Carrollosome traction, it makes the shoes easier to wear. “I’ll wear them when I’m in the mood for stomping down the street,” Carrollo says. “They’re honestly fun to walk fast in because of the platform and how light they are. I could be imagining it, but the foam heel almost gives you a boost with every step.”

[Editor’s note: Some sizes are sold out now, but you can sign up to receive an email when your size is back in stock.]

JournalistHannah Bensonfeels “ready to fulfill all myLast Days of Discofantasies” in the Ineses. The shoes always feel appropriate, whether Benson has worn them to a dinner party, patio bar, or work event, but she tends to wear them when she’s “looking to haveanight — be it fancy, memorable, flirty, or all three.” You might feel some pinching in the beginning, but “trust the process,” says Benson.

Babyteeth’s Aisha Joshi’s feet were “absolutely mangled by heels after a slew of weddings,” but she found reprieve in a pair of Larroude shoes nearly identical to these. At a more recent wedding, she was able to wear them all night. “The only time I ditched them was for the dancefloor when I really needed full mobility.” They’re “very easy to break in as far as heels go,” with the toe box forgiving and the right kitten-heel height.

EditorMallory Riceadmits Maryam Nassir Zadeh’s Roberta has a “diminutive heel,” but “when combined with the girlishness of the ballet shape…it says something along the lines of ‘I honor the occasion, to a degree.’” Rice has had a few Roberta Ballerinas over the years, but her favorite is the silver (“a celebratory neutral,” as she describes it). “I remember popping them on for a friend’s holiday party and feeling that the outfit — a skirt of mostly browns with a yellow top — was a drag until they came into the equation.” It’ll lift up an outfit that might’ve been “sourced from the laundry pile” too.

Elissa Suh, a film critic who writes the newsletterMoviepudding, bought two pre-owned Repetto Camilles on Japanese eBay — in a size 38.5 and a size 39. “Neither pair leaves any blisters, but my toes definitely need a good stretch after a long walk in the smaller size. I can tell that won’t be the case once they’re fully broken in,” says Suh. That’s not to say they aren’t easy to walk in. If you’re heels-shy, they’re “ideal not just because of the baby height of the heel, but the block shape.”

The Weird Real’sAlisha Bansal— a former ballet dancer — can’t help but get a kick out of wearing Repettos, as she told me previously in our guide to thebest mary janes. She’ll wear hers a few times a week. “It’s the perfect everyday height, so you don’t feel like you’re too flat on the ground.”

“No matter the time of day it is or what phase of life I’m in or how many hours I have to be on them, my feet are going to be at least two and a half inches above ground,” says writerIva Dixit. “I want to feel firmly ensconced in a shoe that makes my spine straighter and my gait more authoritative.” Her requirements are simple: “I want to be able to stand on them for hours and walk in them across city blocks and take public transportation.” Dixit wears her Nou mules as “one would wear orthotic shoes.” On the day they arrived, she wore them out to the WSA building downtown, then to Spring Street and the Upper East Side — and back to Brooklyn. “These are the only mules that haven’t sliced and diced the tops of my toes with a hundred tiny little cuts from the friction of the leather inside the vamp, so their construction is very kind to wide feet,” she says. Should you intend to treat them as she does, put metatarsal foot pads “in the front part, where the ball of your foot rests within the shoe…[which] makes the experience of wearing any heel a lot more comfortable.”

“I actually didn’t feel they needed much breaking in,” saysCake Zineco-editorTanya Bushof Stuart Weitzman’s Vinnie Slingback. “I wore them one night to a party in the West Village and then ended up walking all the way to the East Village for a second stop. Voila! They were broken in.” It could be because “magically, the pointy toe doesn’t pinch” and they have a “good amount of ankle support.”

Victoria Filippini, a content creator who writes the newsletterTaking Notes,took her pair of Carel’s Kina mary janes right out of the box and wore them around Paris for the first time. “I got a few rubs, but from then on, I just preemptively used Band-Aids where I could feel them rubbing.” Nonetheless, it was an “honestly fine” break-in process. She now wears them most of the year, including last Christmas, when she wore them to seeThe Nutcrackerright after it snowed — “against my better judgment” — and they braved the slush-covered pavement.

The Kinas were an “Alexa Chung-influenced purchase” forSable Yong, author ofDie Hot With a Vengeance. They ended up being “surprisingly comfortable for what appear to be stiff fancy dress shoes a boarding school girl would wear.” She adds, “They’re not supportive in any orthopedic way, but they’re wide enough for my foot not to feel scrunched and none of the edges cause blisters.” At some point, they’ll mold to your feet. More impressive is their ability to survive “various terrains” — like a farm upstate with “grass that was getting damper throughout the afternoon due to rain” and a tuberose field in Grasse, France.

Socialite Carolyne Roehm was the inspiration for Manolo Blahnik’sCarolyne— before it was a favorite ofCarolyn Bessette-Kennedy’s. Available in either 50-mm. or 70-mm. height, they’re what writerBre Harrisondescribes them as a “low-stakes kitten heel.” Harrison found a pair on the RealReal a few years ago, and they’ve been “really comfortable shoes that I know I’ll hold on to forever and maybe even pass them down.”