Sky-high stilettos may look good on your feet, but they often come at a price: Wearing them for too long can cause blisters and back pain. Thanks to modern cushioning and softer materials, there are smart alternatives to wobbly, pencil-thin heels—and they look just as sophisticated and stylish. After testing eight different pairs, we landed on the most comfortable heels for work, weddings and everyday wear. Our overall winner is the Cole Haan Grand Ambition Pump, which features a chic silhouette and an anatomically contoured footbed that cradles your foot.
To find the most comfortable heels that don’t sacrifice style, we tapped the expertise of Forbes Vetted deputy fashion editor, Kari Molvar, who has written extensively about footwear and rigorously tested all eight of our top picks firsthand. We also consulted with New York City podiatrist Dr. Krista Ammirati Archer to learn more about which features to prioritize in a pair of foot-friendly heels. Read on to see the most comfortable heels that earned the highest marks in our testing process, along with seven more highly rated picks we also recommend.
Most Comfortable Heels Overall: Cole Haan Grand Ambition Pump
Most Comfortable Heels For Work: Naturalizer Michelle High Heel Pumps
Most Comfortable Dress Heels: Margaux The Heel
Most Comfortable Stilettos: Sarah Flint Perfect Pump 85
Most Comfortable Black Heels: Everlane The Italian Leather Day Heel
Most Comfortable Heeled Sandals: Aerosoles Emmex Sandal
Most Comfortable Platform Heels: Naturalizer Joy Sandal
Most Comfortable Affordable Heels: Dream Pairs Annee Pointed Toe Low Chunky Heels
Most Comfortable Heels Overall
A Pump Developed With Scientists To Cradle Your Foot
Cole Haan Grand Ambition Pump
Sizes:5 to 11 |Colors:11 total, including Black and Soft Gold |Materials:Leather, suede | Fit: Runs true to size | Walkability score: 4/5
- What’s notable: There is a high level of padding and support and no pinching in the pointed toe—plus, the silhouette is stylish and versatile.
- What could be better: The stiletto heel might be too high and narrow for some people.
Cole Haan’s best-selling Grand Ambition Pump was developed with the University of Massachusetts Amherst’s Biomechanics Laboratory to deliver serious comfort. This pair has responsive cushioning to create the right level of padding, a contoured footbed and stabilizing traction pads on the outsole. For a pointed-toe pump, reviewers say these heels are incredibly comfortable and easy to walk in.
What our testers say:“These heels look deceptively narrow but once I put them on, I found that my foot had plenty of room. The leather is supple and buttery, and the cushioning in the sole is great—very plush and supportive," Molvar notes. "This pair didn’t require any break-in time either. The only drawback is that the stiletto heel shaft is a bit thin, so it sometimes skidded to the side as I walked, which required me to catch my balance.”
Most Comfortable Heels For Work
Breathable Design And Inclusive Sizing
Naturalizer Michelle High Heel Pumps
Sizes:4 to 12; 6W to 12W |Colors:4 total, including Black and Beige |Material:Leather, patent leather | Fit: Runs true to size | Walkability score: 5/5
- What’s notable: The rounded toe doesn’t pinch, they have a breathable lining and the price is affordable.
- What could be better: The thicker stiletto heel isn’t as stylish as other options.
With over 3,600 5-star ratings on Amazon (and counting), these pumps hold their own in the world of comfort. They come fully loaded with Naturalizer’s Contour+ Technology, which includes foam cushioning, a breathable lining, sculpted insole and heel support. You can choose from a wide range of sizes (from 4 to 12) and both medium and wide widths.
What our testers say:“I was seriously impressed by these heels, which had the best internal padding of all the shoes I tested. These felt pillow-y soft, the sole absorbed moisture and the rounded toe eliminated any foot scrunching. The only negative is that the thicker width of the heel and overall silhouette felt not as stylish as some of the other pairs I tested, but this is still an excellent shoe.”
Most Comfortable Dress Heels
Sophisticated, With A Supportive Fit That Molds With Wear
Sizes:3 to 14; 3N to 14N; 3W to 14W |Colors:11 total, including Black and Fawn |Material:Leather,suede |Fit:Runs narrow |Walkability score:4/5
- What’s notable: Foam padding is built into the sole, the supportive fit contours to your foot, and the craftsmanship is impeccable.
- What could be better: They fit a little narrow (if you need more room, order the wide), and they are on the more expensive end.
Long events and weddings make wearing heels a challenge, especially if you have to walk a fair distance between venues or you’re standing on your feet all night. Margaux gets that and builds comfortable features into the design of its beautiful, smart-chic heels. The 2.5-inch stacked block heel gives you maximum support, and the 5mm foam padding absorbs shock as you walk. This pick also comes in three widths—medium, wide and narrow.
What our testers say: “I was very impressed by the quality of the suede and comfort of this shoe. Reviewers say there is no break-in period, and I found that to be true. I wore these for hours, and didn’t even feel like I was wearing heels.”
Most Comfortable Stilettos
Anatomical Arch Support And Extra Footbed Padding
Sizes:4 to 13 |Colors:13 total, including Black and Taupe |Materials:Leather, suede, lamé, calf hair, satin, canvas or raffia | Fit: Runs small | Walkability score: 4/5
- What’s notable: These luxury, high-quality heels have a unique anatomical arch support and great traction.
- What could be better: They are expensive and run a little narrow.
Stilettos often cause back pain and squeeze your toes within an inch of their life. But Sarah Flint’s shoes are specifically designed to be extremely comfortable and stylish: The wider front minimizes toe crowding and 6mm of extra padding on the footbed reduces leg fatigue. In addition, the inner sole is contoured and padded to fit the shape of your foot, a detail that definitely makes these stand out from your average heels. To deliver a nice lift, the stiletto is also crafted with an internal steel rod, which makes for a sturdy (and, ultimately, comfortable) base. Just note: These run a little small, so the brand recommends sizing up a half-size.
What our testers say: “These shoes are gorgeous. The materials are luxurious and sophisticated, which is hard to find in a comfortable heel. While they’re pointy and high, they’re very wearable. I even tested them on a slippery surface coated with snow and didn’t wipe out.”
Most Comfortable Black Heels
Ballet-Inspired Block Heels
Sizes:5 to 11 |Colors:4 total, including Black and Light Taupe |Materials:Leather,suede | Fit: Runs true to size, slightly wide | Walkability score: 5/5
- What’s notable: The elasticized back holds your foot in place, and they have a comfortable block heel.
- What could be better: They aren't available in wide sizes, and they're only available in four colors.
Black heels strike the right balance between day and night looks, and are an essential part of any shoe wardrobe. Everlane’s ballet-inspired block heels happen to be especially wonderful: The elastic seam at the back provide a snug, chafe-free fit, and the round toe gives your feet room to spread out. This bestseller has 3,000 5-star ratings and is available in a pale pink, light taupe and blush tan—all of which can complement a variety of skin tones.
What our testers say: “I was skeptical about the elasticized back on these heels but was pleasantly surprised at how well it works—it really holds your foot in place without any rubbing. The block heel is perfect, just the right height, and the leather is smooth and not stiff against bare skin.”
Most Comfortable Heeled Sandals
Open-Toe, Block Heel And Cushioned Footpad
Aerosoles Emmex Sandal
Sizes:5 to 12; 6W to 12W |Colors:6 total, including Black and Tan |Material:Faux leather,suede | Fit: Runs true to size | Walkability score: 4/5
- What’s notable: These shoes have a mid-height block heel, adjustable straps and great padding and traction.
- What could be better: The open-toe design is not ideal for bad weather.
Aerosoles has long prioritized comfort in its heels. The top-rated Emmex Sandal has a supportive block heel and an ergonomically molded footbed that cushions your entire foot. It also features the brand’s signature diamond flex outsole (a diamond pattern on the bottom of the shoe that disperses friction and provides a better grip). This pair comes in both wide and medium widths.
What our testers say: “I found these open-toe sandals versatile to dress up or down and the adjustable straps let me customize the fit to my exact foot. Since these are made from faux leather, the material isn’t as soft as luxurious as other options, and the straps do have the potential to rub on the front of your ankle. But overall, the construction is solid and I walked around in these very happily.”
Most Comfortable Platform Heels
A Platform You Can Wear All Day
Naturalizer Joy Sandal
Sizes:4 to 12; 6W to 12W |Colors:18 total, including Light Bronze Leather and Berry Suede |Materials:Leather,suede or satin | Fit: Runs true to size, slightly wide | Walkability score: 3/5
- What’s notable: They’ve got a stylish, elevated look and plush padding—and come in a versatile range of colors.
- What could be better: The back heel could be better designed.
A platform is surprisingly comfortable because it gives you plenty of height but minimizes the incline, thus easing the strain on the balls of your feet. Naturalizer’s Joy sandal is well cushioned and breathable, featuring a lightweight base and an adjustable ankle strap to secure your foot in place. Also great: This pick comes in dozens of colors (plus a wide width).
What our testers say: “I loved the height of these platform heels, and the suede lining felt soft and smooth against my bare skin. The back of the heel could have been a little tighter to hold my foot more securely in place, but other than that aspect, these platforms are well designed and comfortable to wear to an event or party.”
Most Comfortable Affordable Heels
Well Priced, Blister-Free Option
Dream Pairs Annee Pointed Toe Low Chunky Heels
Sizes:5 to 11; 7W to 10W |Colors:20 total, including Floral and Black |Materials:Suede, nubuck or faux leather | Fit: True to size, slightly wide | Walkability score: 3/5
- What’s notable: The adjustable straps and spacious design accommodate wider feet—all for an affordable price.
- What could be better: The materials aren’t as high quality as others.
When you want some height but can’t be bothered with a pencil-thin heel, this block-shaped alternative makes for a comfortable option. This 2.25-inch heel features an anti-slip outsole and a latex insole that provides plenty of cushion. The adjustable strap also allows you to create a snug fit to reduce friction and rubbing. If you want affordable heels to wear occasionally or as a back-up pair, these Dream Pairs sandals fit the bill.
What our testers say: “Between the modest heel height, adjustable straps and roomy design, they’re comfortable and no-fuss. They’re not the most stylish of the options I tested, and the material is not as high quality as some of the more expensive shoes on this list, but this is a good pair to toss in your bag or travel with.”
MORE FROMFORBES VETTED
More Top Picks To Consider
In addition to the heels we recommend above, we also have our eye on these newly launched comfortable pumps, sandals, slingbacks and espadrilles. If the above styles don’t work for you, check out these other highly rated options:
Bunion-Friendly Slingbacks
Sole specifically designs shoes that are comfortable for women with wide feet, bunions and other foot problems. The brand sneaks three layers of cushioning into the soles, and a hidden “bunion bed” panel cushions and hides inflamed joints. While comfort is its main priority, Sole doesn’t skimp on style: These chic, premium leather slingbacks are part of its Sole Bliss X Elizabeth Stewart Collection, a collaboration with Hollywood fashion stylist Elizabeth Stewart.
Open Toe Design That's Great For Wide Feet
Loeffler Randall Mikel Ankle Strap High Heel Sandals
These shoes have a lot going for them: The low block heel is more manageable to walk in than a skinny stiletto, the adjustable ankle strap adds support, the open square toe offers extra width and there is a padded footbed for comfort. The bow detail and stylish raffia material are added bonuses. If you find raffia too scratchy, this pair also comes in six shades of soft leather.
Block Heels Keep Feet Stable
Stuart Weitzman Benni 75 Sandals
Stuart Weitzman isn’t known as a “comfort” brand, but it's deserving of that reputation. Case in point: The stylish Benni 75 sandals have several functional features that make them practical for walking around and standing for long periods of time. They’re available in a wide width to accommodate wider feet and bunions. The flared block heels keep feet stable, and the belt-like straps also hold feet firmly in place.
Classic Pump, With A Comfortable Twist
Aerosoles Minetta Mid-Heel Pumps
If you’re looking for a basic work pump that won’t squeeze your toes or make your heels ache, the Minetta is a solid choice. It has a padded footbed for comfort and a stable, easy-to-walk-in medium-height block heel. Plus, it comes in a wide width if you need a little extra room. These pumps aren't flashy, but they are a classic look that will complement a variety of work ensembles.
Espadrilles You Can Actually Walk In
Castaner Bromelia Frayed Canvas Wedge Espadrilles
Espadrilles—especially ones as high as these—can sometimes feel like you are walking around with bricks strapped to your soles. But the Castaner espadrilles are soft, agile and flexible. Forbes Vetted contributing fashion writer Lesley Rotchford wears Castaners all summer long (she has them in two colors) and finds them easy to walk in, comfortable to stand in and chic enough to wear with basically anything in her wardrobe.
Perforated Leather Offers Ventilation
Beautiisoles Flynn Slingback Pointed Toe Pump
Between the breathable perforated leather, 6mm memory foam insole, adjustable strap and sensible kitten heel, these slingbacks are a strong contender for your warm weather work shoes. They come in rich traditional colors like black, brown and navy, as well as soft summer shades like off-white and sky blue—which are sure to put some spring in your step.
Stilletos With Sneaky Support
This looks like your classic high-end pointy toe stiletto, but under the surface lies a specially designed footbed that increases stability, adapts to the natural shape of your foot and reduces fatigue. While you probably won’t want to trek around New York City in these all day, they will be perfectly comfortable for walking around your office or a party.
Why Trust Forbes Vetted
At Forbes Vetted, we’ve researched, tested and written extensively about fashion and footwear topics.
- Deputy editor Kari Molvar has experience testing a variety of shoes, including the most comfortable walking sandals and the best walking shoes for women. She formally tested all eight pairs of heels that we recommend as our top picks.
- Co-authors Stephanie Montes and Lesley Rotchford are both regular Forbes Vetted contributors and have several years of experience covering lifestyle and fashion.
- For this guide, we enlisted the advice and expertise of New York City-based podiatrist Krista Ammirati Archer, a Doctor of Podiatry Medicine (DPM) and an Associate of the America Board of Multiple Specialties in Podiatry (ABMSP).
- This story is continually reviewed to ensure all products and prices are accurate. It was last updated in July 2024 by fashion writer Claire Epting.
How We Tested The Most Comfortable Heels
Molvar first considered a variety of shoes in different styles, heel heights and price levels. She narrowed down the top picks based on those that received the highest scores for comfort, grip and traction, quality of materials and overall value for the price.
- Molvar then tested each of the top eight contenders, wearing them on different surfaces, including hardwood floors, concrete and stone. She also road tested a few pairs during a snow storm to see how the heels held up in inclement weather.
- In addition to her own scoring and evaluation, Molvar read independent user reviews to ensure each of the picks on this list earned high marks (at least 4 out of 5 stars) from other testers with different foot types, conditions and needs.
- To mimic the friction and rubbing caused by long-distance walking, Molvar also tested certain pairs by wearing them on a treadmill to do a final check on any pairs where there was the potential for discomfort or blisters.
What To Look For In The Most Comfortable Heels
Although the style and look depend on personal preference, certain factors provide a variety of comfort levels. Height and incline, as well as fit and materials, all play a role in how your feet feel at the end of the day.
Height
When it comes to heels, the higher the back, the more pressure it places on the ball or front of your feet and toes. A platform in the front can help lower the incline, which alleviates the pressure on the ball while still giving you plenty of height. Block heels and kitten heels are great options for lower heel heights.
Heel Type
Certain heel types are more comfortable than others. Archer says in order of comfort, she would recommend starting with a wedge or a platform, then a block heel, a kitten heel and then a stiletto. Wedges and platforms offer the most comfort because they distribute your weight evenly across your foot. In addition, the more cushioning a heel has, the longer you’ll be able to wear it without experiencing pain. However, you always have options. If you love a certain heel without any cushioning, you can always add a separate sole insert for extra support.
Materials
When it comes to your comfort, the materials are just as important as the heel height and design of your shoe. Dr. Archer recommends investing in shoes made of soft leather without any seams in the forefoot toe box. Genuine leather is easier to break in than other materials; it softens over time and conforms to the shape of your foot, ultimately resulting in a more comfortable fit. Breathability is important, too. “In general,” she says, “leather, cotton mesh or canvas allow the best circulation.”
Fit
One of the main culprits of an uncomfortable shoe is a poor fit. “Shoe sizes vary depending on the designer,” Archer says. She recommends getting your feet measured regularly, as your size can change over time. “Most women’s shoe size changes after having kids, and with the progression of deformities like bunions or hammertoes.” She notes that a proper foot measurement includes both your length and width sizes.
Which Brand Makes The Most Comfortable High Heels?
According to our testing, the most comfortable heels are made by Cole Haan. The brand’s Grand Ambition Pump earned all-around praise for its soft cushioning and soft, buttery leather upper. It’s no accident that Cole Haan’s heels are superior in the comfort department: This style was developed with the University of Massachusetts Amherst’s Biomechanics Laboratory to ensure it delivered maximum support.
Which Heels Are Easiest To Walk In?
Platforms tend to be the most comfortable heels for walking, since your foot rests on an even plane, without any incline. If that’s not the type of shoe you’re looking to wear, consider a pair of heels that has a wide toe box, which provides breathing room at the widest part of your foot and allows your toes to splay out. The longer you walk or stand on your feet, the more your feet will swell. For that reason, you want a design that won’t constrict your feet but isn’t so loose that it will cause slippage. Often, making sure your shoes are wide enough solves this issue.
What Are The Most Comfortable Heels For Wide Feet?
As you’d imagine, heels that come in wide-width options are best for those who want extra room. Not all heels offer this fit option, though. In that case, your best bet is sometimes to size up and use an insert to eliminate any extra space at the back of your heel. Why this works: Often, a larger size gives you more width and more length. If you only want the width, you’ll need to make adjustments to fill the gap in the back toward your heel, which an insert can help with (while also providing nice padding in the sole). Also look for strappy heels that can be adjusted on the sides and fully enclosed pumps with a low vamp—the cut-out at the front of a shoe—which naturally fits a wider foot more comfortably.
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