The Most Comfortable Heels Worn By Founders And Executives

Stilettos are not typically known for comfort, but Sarah Flint’s Perfect Pump is made from luxurious materials (burnished Italian calf leather with soft leather lining) that make it as easy to wear as slipping into a pair of flats. It has an elegant pointed toe and 3.3-inch heel, and there are several comfort features: extra footbed padding to cushion each step, anatomical arch support and a slightly wider than normal toe box so your toes won’t be squished. “Sarah Flint pumps are my favorites for nights and weekends in Seattle,” says Dr. Heather Rogers, founder of Doctor Rogers. “They’re cute, comfortable and come in every color. I have three pairs in my closet at any time and order another pair as soon as one gets roughed up.” Rogers also likes that she can wear them all day in her dermatology clinic if she plans to dress up for an after-work event. (For special occasions, she also recommends Manolo Blahnik’s Black Suede Pointed Toe Pumps, and for trips where she needs an affordable heel that can be worn while running around, she likes Ann Taylor’s Mae Leather Pumps.)

Veronica Beard is a female-founded brand known for its sharp tailoring and classic-yet-cool pieces that take you from the office to post-work drinks with ease. Courtney Claghorn, founder of Sugared + Bronzed, loves the Via Suede Mid-Heel Sandals, which provide “walk-all-day” comfort while still giving her height. They have a slide-on design so you don’t have to fuss with buckles or ankle straps, and the high-quality materials (in soft suede or leather) are comfortable right out of the box. “These are my ultimate work-to-weekend shoes,” says Claghorn. “I wear them to elevate casual looks, pair them with dresses for work meetings, or wear them out for dinner and drinks.” For a slightly higher heel height and playful twist-front detail, she’s also a fan of Veronica Beard’s Ganita Knot-Front Sandal.

Manolos are synonymous with impeccable craftsmanship and timeless appeal, regardless of the season or current trends. The brand is worn by celebrities, royals and everyday women who want to look and feel their most confident selves. Case in point: The Carolyne Leather Low-Heel Slingback Pump has a sophisticated pointed toe, a walkable 2-inch heel and sleek slingback that makes it easy to slip on and off. “I’m constantly on the move—driving, standing, working, living—I need shoes that can keep up with real life while still feeling elegant,” says Danuta Mieloch, esthetician and founder of Rescue Spa. “They don’t demand attention, but earn it. They’re comfortable, refined and versatile enough to carry me through every occasion.” Another of Mieloch’s favorite shoes is the Carla Pump 80 from The Row, which she says “represents the kind of quiet luxury I truly believe in.”

Founded in 1972, Tony Bianco has become popular with the fashion crowd thanks to its on-trend silhouettes coupled with high-quality materials. This chic stiletto has a 3.3-inch heel and side cutouts that reveal more of the foot. The suede leather has a soft, velvety feel, and there are plenty of colors to choose from, ranging from bright red to more subdued neutrals. “As an Australian founder, I love supporting Tony Bianco, and have been wearing the brand’s heels since my news reporting days, running through crime scenes and rushing to breaking news,” says Naked Sundays founder Samantha Brett. “They strike the right balance between sleek and practical. The heel height is flattering without being extreme, and I can wear them from a board meeting straight to dinner.”

Some heeled boots can border on clunky or utilitarian, but Mansur Gavriel’s popular glove boots strike the right balance between comfort and style. The smooth leather molds to your feet for all-day wear and ages well, and the rounded toe prevents foot scrunching as you go about your day. “I’m obsessed with the Glove Boot by Mansur Gavriel,” says Kegan Fisher, co-founder of Frank Darling. “The leather is butter-soft—honestly, all of their shoes are—and the heel feels substantial without being hard to walk in.” Fisher also likes that these boots work with almost everything in her closet, and the “seam detail along the toe makes them feel thoughtful rather than basic.”

Block heels are a great option for those who typically don’t wear high heels, as the wider base provides more stability when walking. This pick from Aquazzura is crafted from black suede and features tiny bows along the slingback strap, adding visual interest to this otherwise classic style. “I love the look of kitten heels, but living in New York City means cobblestone streets absolutely destroy them, so I stick to block heels that I can comfortably run around in all day,” says Nadine Kahane, founder of Stone & Strand, who owns a similar version of this shoe. “Comfort is non-negotiable for me, which means I only buy real leather shoes that are cushioned, supportive and built to last.” Kahane adds that she’s very much a jewelry girl, so when it comes to shoes, she prefers classic, versatile colors that work with everything and can easily transition from day to night. (The Roger Vivier Trompette 45 Patent Leather Pumps are another block heel style she recommends.)

Gray Matters designs are sculptural and polished, with unique details like rock and egg-shaped heels (the brand’s Egg Mules are considered one of the bestsellers) that are made to be shown off. Jennifer Behr, founder and creative director of her namesake brand, is always on the hunt for comfortable shoes and considers the Gray Matters Clara Pumps among her favorite shoes by far. “I need to be able to run around the city for design meetings and appointments, and I am just not willing to be in pain,” says Behr. “I have the Clara Pumps in two colors. They are a classic shoe but have a little edge.” She takes them to market in Paris, as the wider heel is perfect for cobblestone streets, and she also owns the Mildred Mules, which can be dressed up or down for any occasion.

The Row—founded by Mary-Kate and Ashley Olsen—is known for its “quiet luxury” aesthetic, which champions timeless and classic silhouettes that anchor your closet. The brand’s Bare Sandal is a great example of that ethos, with its simple, clean lines that let the materials speak for themselves. “These shoes are understated but incredibly well designed,” says Parke founder Chelsea Parke. “The [leather] construction makes them comfortable enough to wear for hours, while still feeling timeless and refined. Living in Miami, these are the best for year-round wear.” A thin, asymmetrical strap keeps your toes in place, and there’s a delicate buckle around the ankle that can be adjusted for a secure fit.

If sky-high stiletto heels aren’t your thing, a wedge heel may be a more wearable and approachable option that still gives you a bit of extra height. Toteme’s Sharp Naplack Wedge Pumps feature a sculptural half-wedge heel that Jenny Lei, founder of Freja, calls “surprisingly comfortable.” They’re made from naplack leather, a type of patent leather with a distinctly wrinkled and crinkly texture. “I broke them in during a 45-minute walk through Parisian cobblestone streets and hills and came out unscathed,” says Lei, who has been wearing this pair for several months. “I wear a lot of black, but my latest obsession is anything in this deep, glossy brown-red shade.” She styles these heels with dark denim or tailored trousers, or with a long skirt and sheer ankle socks.