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  • 11 Most Comfortable Heels 2023
11 Most Comfortable Heels 2023

11 Most Comfortable Heels 2023

Benjamin FosterSeptember 12, 2023

Table of Contents

Toggle
    • Cole Haan Grand Ambition Pump
    • Christian Louboutin Pumppie Patent Red Sole Pumps
    • Naturalizer Michelle High Heel Pumps
    • Aerosoles Emmex Sandal
    • Naturalizer Joy Sandal
  • What To Look For In The Most Comfortable Heels
    • Height
    • Materials
    • Fit
  • What Is The Most Comfortable Heel Type?
  • How Do You Select Higher Heels That Are Also Comfortable?
  • What Other Design Features Make A Heel More Comfortable?

The problem with some of the most comfortable heels on the market is they tend to look comfortable—and downright orthopedic. Wearing stylish sky-high stilettos often comes at a price, though, (think blisters and back pain). But thanks to modern cushioning and softer materials, there are smart alternatives to wobbly, pencil-thin heels. Our top pick overall, Cole Haan Grand Ambition Pump, proves the point with a chic silhouette and anatomically contoured footbed that cradles your foot.

The most comfortable heels have smart details—from cushioning to arch support—built into a chic … [+] design.

ILLUSTRATION: FORBES / PHOTO: RETAILER

To find the most comfortable heels that don’t sacrifice style, we tapped the expertise of Forbes Vetted senior fashion editor, Kari Molvar, who has written extensively about footwear and rigorously tested everything from sandals to sneakers firsthand, and we also consulted with New York City podiatrist Dr. Krista Ammirati Archer. Here, 11 of the most comfortable heels that we highly recommend, and for more options, we also have guides to the best ballet flats and women’s loafers.

Cole Haan

Cole Haan Grand Ambition Pump

Sizes: 5-11 | Colors: 4 total, including Black and Irish Coffee | Material: Leather, suede

Cole Haan’s bestselling 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 the reviews say: “Excellent fit, comfortable and a very nice quality, buttery leather. The tiny platform is nice, not obvious and will provide some extra shock absorption and traction on the polished stone floors at work.” —Zappos


Sizes: 4 to 13 | Colors: 23 total, including Black and Taupe | Material: Leather, suede, lamé, calf hair, satin, canvas, raffia

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 6 millimeters of extra padding on the footbed reduces leg fatigue. To deliver a nice lift, the stilletto 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 the reviews say: “These are the most comfortable work pumps I’ve ever owned. There is no break in time. I can easily walk around and wear them all day. I think they get better as you wear them.”—Sarah Flint


Sizes: 3 to 14 | Colors: 10 total, including Rose Nappa and Burgundy Suede | Material: Leather, suede

Long work days make wearing heels a challenge, especially if you commute or walk to your office. Margaux gets that, and builds comfortable features into the design of their beautiful, smart-chic heels. The 2.5-inch stacked block heel gives you maximum support, for example, and the 5-millimeter foam padding absorbs shock as you walk. This pick also comes in three widths—medium, wide and narrow.

What the reviews say: “This heel is the perfect heel for everyday wear around the office. I’m really impressed by the quality of the suede and leather and the comfort of the shoe. People weren’t lying when they say that there is no break in period!” —Margaux


Net-A-Porter

Christian Louboutin Pumppie Patent Red Sole Pumps

Sizes: 5 to 12 | Colors: 2 total, including Black and Cream | Material: Leather

It doesn’t get more designer than the red soles of Christian Louboutin and this Pumppie heel is quite possibly the most comfortable shoe the brand makes. The 3.25-inch heel and rounded toe is a recipe for all-day wear and the classic leather colors go with everything. 


Naturalizer

Naturalizer Michelle High Heel Pumps

Sizes: 4 to 12 | Colors: 4 total, including Black and Beige | Material: Leather, patent leather

With over 3,000 five-star reviews 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. And you can choose from a wide range of sizes (from 4 to 12) and both medium and wide widths.

What the reviews say: “I have many weddings on the calendar this year and this Michelle pump from Naturalizer has been my ‘go to’ shoe for all my fancy occasions. In the nude, it goes with everything and it visually extends the leg. They fit my wide foot and they are comfortable enough to wear all night long, even dancing. “ —Amazon


Sizes: 5 to 11 | Colors: 3 total, including Black Suede and Almond Leather | Material: Leather, suede

The perfect black heel is comfortable, stylish and goes with everything from silk skirts to slouchy jeans. Reformation’s modern design provides the right lift, with a 3-inch sculptural heel that has a wider base than your usual pointy stilettos, which adds stability. The upper is made from either soft calf leather or satin-like suede to ensure a blister-free experience.

What our fashion editor says: “There’s certainly no shortage of black heels out there. Reformation’s stand out for being thoughtfully designed for all-day wear with details, like a chunkier stiletto heel, that add comfort in unexpected ways.”


MOST POPULAR

Sizes: 5 to 11 | Colors: 5 total, including Black and Light Taupe | Material: Leather, suede

Nude 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 back has an elastic seam to provide a chafe-free, snug fit and the round toe gives your feet room to spread out. This bestseller has 3,000 five-star ratings and is available in a pale pink, light taupe and almond shade, all of which can complement a variety of skin tones.

What the reviews say: “I ordered these in the beige and had to get them in black. They are the most comfortable shoes. I don’t usually wear shoes with high heels but these are perfect for wearing with anything.” —Everlane


Sizes: 5 to 11 | Colors: 2 total, including Black and Tan Leopard | Material: Leather, calf hair

A kitten heel gives you a bit of height to dress up any look without a high incline to put pressure on your soles. This pointed-toe by Vionic—a brand developed with podiatrists—is crafted with a deep heel cup to hug your foot and a forefoot contour for extra comfort on the balls of your feet. The adjustable ankle strap makes them easier to walk in.

What the reviews say: “I hate to sound dramatic, but these shoes are life changing for me. I have bunions and need arch support. Finally, a shoe that looks great with work slacks!” —Zappos


Aerosoles

Aerosoles Emmex Sandal

Sizes: 5 to 12 | Colors: 6 total, including Black and Tan | Material: Faux leather, suede

Aerosoles has long prioritized comfort in their heels. The top-rated Emmex Sandal has a supportive block heel, an ergonomically molded footbed that cushions your entire foot and 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 also comes in wide and medium widths.

What the reviews say: “Obsessed with these shoes. They are so cute, so easy to walk in, and so comfortable. I’ve worn them all over, walking downtown, and for full days. Can easily be dressed up or down. True to size. Perfect height. I need more colors now.” —Aerosoles


Naturalizer

Naturalizer Joy Sandal

Sizes: 4 to 12 | Colors: 17 total, including Light Bronze Leather and Berry Suede | Material: Leather, suede, satin

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 with a lightweight base, and has an adjustable ankle strap to secure your foot in place. Also great: This pick comes in dozens of colors (plus a wide width).

What the reviews say: “These shoes are so comfortable—I’ve worn them in nude as a wedding guest recently, and can wear them all night long, on my feet and dancing, without any discomfort after hours of wear. You get awesome height comfortably [due] to the build of the shoe [that’s] the perfect combo of platform and heel.”—Zappos


Sizes: 5 to 11 | Colors: 20 total, including Floral and Black | Material: Suede, nubuck, faux leather

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.

What the reviews say: “Super comfortable, fits as expected, matches and looks good with pretty much anything. As someone who usually avoids wearing heels, [I’m] so happy to have found this.” —Amazon


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. New York City podiatrist Dr. Krista Ammirati Archer, ABMSP, points out that “balance, stability and foot positioning combine for the most comfort.” Here’s what else to keep in mind:

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.

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 soft leather without any seams in the forefoot toe box. Genuine leather is easier to break in than other materials, which means it softens over time and conforms to the shape of your foot, ultimately resulting in a comfortable fit. “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,” Dr. Archer says, adding that, “sometimes they’re very different.” 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.


What Is The Most Comfortable Heel Type?

Dr. 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. However, you always have options. If you love a certain heel without any cushioning, use a sole insert.

How Do You Select Higher Heels That Are Also Comfortable?

Oftentimes, the primary benefit of heels is the boost in height it gives you. So if you’re in the market for higher heels but you’re also looking to feel comfortable, consider shopping for a platform with a lower incline. Another option, according to Dr. Archer, is “wedge styles, which have a thick sole under forefoot, because they can reduce the slope from heel to toe, thereby increasing the level of comfort.”

What Other Design Features Make A Heel More Comfortable?

Aside from the heel high, material and incline, there are other design features that can make a shoe fit better and feel more comfortable. Dr. Archer says, “wide-size options are always great to ensure that you are not putting pressure on the nerves between the toes.” She also recommends heels with straps to provide ankle support and those with a wide or square-shaped toe box rather than a point to allow your feet room to spread out.

Cole Haan Grand Ambition Pump, Comfortable, Heels

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