Skip to Content

Every item on this page was chosen by a Woman's Day editor. We may earn commission on some of the items you choose to buy.

The 20 Most Comfortable Heels of 2023 for Style and Support

These are the best heels for work, weddings, and every occasion in between — with podiatrist recommendations.

By Samantha Lawyer and Elizabeth Berry
Jump to Products
best comfortable heels cole haan grand ambition pump and lulus harper ankle strap heels
Cole Haan/Lulus

We’ve all been there: counting down the seconds until it’s time to take off a painful pair of heels. Whether you’ve dressed up for work, a special event, or everyday errands, wearing the wrong shoes can be frustrating and debilitating. Especially if you’re managing bunions, plantar fasciitis, or other foot related issues, unsupportive heels can be the culprit of some serious damage, which is surely not worth it no matter how pretty the pair is. Believe it or not, there are comfortable high heels out there that you can stand in all day, in a variety of styles to fit your needs.

Based on the advice of experts and hundreds of online reviewers, this list highlights the best, most comfortable heels currently on the market. You’ll find options in a range of heel heights, from kitten to ultra high, as well as different silhouettes and materials. Additionally, we’ve included general advice on what to look for in comfortable heels to guide your shopping, so you can feel confident that you’re purchasing the right pair(s). And while you’re browsing, you may also want to check out our picks for other types of comfortable shoes, like chic ballet flats, trendy cloud slides, cushioned running sneakers, and supportive work shoes you can stand in all day.

The most comfortable heels to buy in 2023:

  • Grand Ambition Pump

    Best Overall Comfortable Heels

    Cole Haan Grand Ambition Pump

    $100 at Cole Haan
    Read more
  • Harper Ankle Strap Heels

    Best Affordable Comfortable Heels

    Lulus Harper Ankle Strap Heels

    Read more
  • Suede Collette Heel

    Most Comfortable Sustainable Heels

    Soludos Suede Collette Heel

    Read more
  • Michelle Pump

    Most Comfortable Classic Pumps

    Naturalizer Michelle Pump

    Read more
  • Ambyr Joy Medium/Wide Pump

    Best Heels for Plantar Fasciitis

    Clarks Ambyr Joy Medium/Wide Pump

    Read more

Meet the Experts

  • Randy Brangman is a Licensed Physical Therapist and Exercise Therapist and former long distance runner.
  • Dr. Suzanne Levine is a Board Certified Podiatric Surgeon and author.
  • Dr. Hillary Brenner is a Board Certified Podiatric Surgeon practicing in New York City.
  • Dr. Nelya Lobkova is a Board Certified Surgical Podiatrist and founder of Step Up Footcare located in New York City.
Best Overall Comfortable Heels

Cole Haan Grand Ambition Pump

On Sale
Grand Ambition Pump
Best Overall Comfortable Heels

Cole Haan Grand Ambition Pump

Now 44% Off
$100 at Cole Haan$252 at Walmart$100 at Zappos
Credit: Cole Haan

These science-approved heels, developed with the help of biomechanics at the University of Massachusetts Amherst, check all the boxes when it comes to comfortable shoes. They feature premium leather, a contoured footbed, layers of cushion, and stabilizing traction, all for a sale price of less than $100.

Heel Height: 3" | Material: Leather | Size Range: 5-11 | Colors: 2

Best Affordable Comfortable Heels

Lulus Harper Ankle Strap Heels

Harper Ankle Strap Heels
Best Affordable Comfortable Heels

Lulus Harper Ankle Strap Heels

Now 20% Off
Credit: lulus

A low heel isn’t necessarily a comfortable one, but reviewers rave about this pair from Lulus. With long-lasting support and suitability for a variety of occasions, these shoes offer a lot of potential at an affordable price point.

Heel Height: 2.5" | Material: Synthetic | Size Range: 5-11 | Colors: 17

RELATED: The Best Pairs of Work Pants That Don't Cost a Fortune

Most Comfortable Sustainable Heels

Soludos Suede Collette Heel

Suede Collette Heel
Most Comfortable Sustainable Heels

Soludos Suede Collette Heel

Now 20% Off
Credit: Soludos

These French-inspired suede heels are extremely comfortable without sacrificing height, thanks to a discreet built-in platform and padding. Their outsole is also made from 40% recycled rubber, which makes them a sustainable fashion purchase.

Heel Height: 3.5" | Material: Suede | Size Range: 5-11 | Colors: 3

Advertisement - Continue Reading Below
Most Comfortable Classic Pumps

Naturalizer Michelle Pump

On Sale
Michelle Pump
Most Comfortable Classic Pumps

Naturalizer Michelle Pump

Now 30% Off
Credit: Naturalizer

With over 700 5-star reviews and counting, these pumps have been thoroughly vetted for comfort. They score highly thanks to Naturalizer's Contour+ Technology, which includes foam cushioning, breathable lining, a sculpted insole, and heel support.

Heel Height: 3" | Material: Leather, Patent Leather, Suede or Fabric | Size Range: 4-12 | Colors: 4

Best Heels for Plantar Fasciitis

Clarks Ambyr Joy Medium/Wide Pump

On Sale
Ambyr Joy Medium/Wide Pump
Best Heels for Plantar Fasciitis

Clarks Ambyr Joy Medium/Wide Pump

Now 16% Off
Credit: Clarks

These Clarks pumps feature an Ortholite footbed that offers protection against a variety of foot-related pains. One 5-star reviewer shared that, "I have been searching forever for shoes that fit the bill and these are it! I have a history of a broken ankle on one side and also plantar fasciitis. I can actually wear these adorable shoes and I love it since most comfortable heels look like old lady shoes. Fit is true to size and bonus, I did not get any blisters!"

Heel Height: 3.5" | Material: Leather | Size Range: 5-12 | Colors: 2

Most Comfortable Wedding Guest Shoes

Naturalizer Taimi Strappy Dress Sandals

On Sale
Taimi Strappy Dress Sandals
Most Comfortable Wedding Guest Shoes

Naturalizer Taimi Strappy Dress Sandals

Now 10% Off
Credit: Naturalizer

You can dance all night with these dress sandals that have over 3,000 5-star reviews on Amazon. One happy customer who wore them to a wedding wrote, "I’m 68 and can’t wear the really high heels anymore. These were just right!! I read one review that said she never felt like taking them off!( I thought oh ya right!) but I’m here to say the same. I wore these from 4pm until 1030pm and they never hurt my feet!"

Heel Height: 2.25" | Material: Leather | Size Range: 4-12 | Colors: 7

Advertisement - Continue Reading Below
Most Comfortable Heeled Sandals

Madewell The Saige Double-Strap Sandal in Leather

Best Seller
The Saige Double-Strap Sandal in Leather
Most Comfortable Heeled Sandals

Madewell The Saige Double-Strap Sandal in Leather

Now 18% Off
Credit: Madewell

These double-strapped Madewell sandals feature comfy details like Cloudlift Lite padding and a stacked heel. One satisfied reviewer called them her "go-to heel" and wrote, "These got a lot of wear already - and they are SO comfortable! The padded straps didn't rub or give me any trouble on the first wear. I really love them."

Heel Height: 2.5" | Material: Leather | Size Range: 5-12 | Colors: 3

Best Heels for Standing All Day

Everlane The Italian Leather Day Heel

The Italian Leather Day Heel
Best Heels for Standing All Day

Everlane The Italian Leather Day Heel

Credit: Everlane

Everlane's two-inch block heel is comfortable enough to walk in all day long thanks to its buttery Italian leather, rounded toe, and elasticized back. With over 3,000 5-star reviews, it's one of the most beloved pairs on this list.

Heel Height: 2" | Material: Italian leather | Size Range: 5-11 | Colors: 5

Most Comfortable Kitten Heels

Aquatalia Pasha Pump

On Sale
Pasha Pump
Most Comfortable Kitten Heels

Aquatalia Pasha Pump

Now 57% Off
Credit: Aquatalia

Dress up any casual outfit with these classy suede kitten heels, which are low in height to keep you pain-free and looking fabulous. One reviewer wrote: "These are the most comfortable shoes I have ever owned," and "I don't think I will ever buy any other brand!"

Heel Height: 1.8" | Material: Suede | Size Range: 5-12 | Colors: 8

Advertisement - Continue Reading Below
Most Comfortable Heels for Work

Margaux NY The Heel

The Heel
Most Comfortable Heels for Work

Margaux NY The Heel

Credit: Margaux

Handcrafted in Spain, these elegant Margaux blocks heels are ready to wear to the office straight out of the box. One happy customer wrote that she was "Naturally a little apprehensive at the 'break in period'...well there was no 'break in period'...my 37.5 Narrow fit like a glove! Classy, professional and super comfy. Highly recommend."

Heel Height: 2.5" | Material: Italian nappa leather | Size Range: 3-14 | Colors: 9

RELATED: Best Work Bags for Women That Make Commuting Easy

Best Comfortable Podiatrist-Backed Heels

Mollie Chalk Reptile Emboss

Mollie Chalk Reptile Emboss
Best Comfortable Podiatrist-Backed Heels

Mollie Chalk Reptile Emboss

Credit: Frankie4

Australian brand Frankie4 is a podiatrist founded company that aims to maximize women's comfort and wellness through their cleverly designed shoes. Board Certified Podiatric Surgeon Dr. Suzanne Levine can personally vouch for the brand, telling Woman's Day, "I had hours of comfort while I toured Paris in my Frankie4 heels." While there are several supportive Frankie4 options, we love the Mollie pair for their ankle straps and arch support.

Heel Height: 2" | Material: Leather | Size Range: 6-13 | Colors: 2

Most Comfortable Mary Jane Style Heels

Sam Edelman Jildie

Jildie
Most Comfortable Mary Jane Style Heels

Sam Edelman Jildie

Now 25% Off
Credit: Sam Edelman

Customers love these Mary Jane heels for their spacious square toe, which is especially helpful for wide feet. One reviewer raved that, "These shoes are EVERYTHING!!! The fit and width are on point and true to Sam Edelman style. I love this shoe because it has a chunky heel and square toe. I have had bunion surgery and am not able to wear the pointy toe fashioned shoes anymore. Thanks Sam Edelman for making this wonderful shoe!"

Heel Height: 4" | Material: Patent leather | Size Range: 5-12 | Colors: 9

Advertisement - Continue Reading Below
Most Comfortable Day-to-Night Heels

aerosoles Women's Sandal

Women's Sandal
Most Comfortable Day-to-Night Heels

aerosoles Women's Sandal

These Aerosoles sandals are casual enough for daytime activities yet can easily transition to evening wear for those times when an outfit change isn't possible. They feature a very slight pitch and a diamond flex outsole to keep you comfortable for hours on end.

Most Comfortable Platform Heels

Camilla Platform

Best Seller
Camilla Platform
Most Comfortable Platform Heels

Camilla Platform

Credit: Inez

Don't let the height and chic design of Inez's Camilla platform fool you: these shoes are truly comfortable enough for hours of wear. They're handcrafted from soft Spanish leather and have a supportive custom insole, plus the ankle strap helps to keep you feeling secure.

Heel Height: 3.9" | Material: Spanish leather | Size Range: 6-10.5 | Colors: 3

Most Comfortable T-Strap Heels

Michael Kors Becker Block Heel Platform Sandal

Becker Block Heel Platform Sandal
Most Comfortable T-Strap Heels

Michael Kors Becker Block Heel Platform Sandal

Now 35% Off
Credit: Michael Kors

Dr. Suzanne Levine says Michael Kors is one of her personal go-to brands for comfortable and stylish heels. These ones feature a supportive ankle strap, and one enthusiastic reviewer shared that they feel like "walking on pillows. The perfect fit."

Heel Height: 4" | Material: Leather | Size Range: 6-10 | Colors: 3

RELATED: The Best Fisherman Sandals

Advertisement - Continue Reading Below
Most Comfortable Heels to Splurge On

Sarah Flint Perfect Pump 85

Perfect Pump 85
Most Comfortable Heels to Splurge On

Sarah Flint Perfect Pump 85

Credit: Sarah Flint

If you're looking to invest in a pair of celebrity-approved heels, bloggers (and even royals like Meghan Markle) swear by Sarah Flint pumps. This pair features practical elements like an expanded toe box, anatomical arch support, and extra footbed padding, that all help justify the high price point.

Heel Height: 3.3" | Material: Italian suede | Size Range: 4-13 | Colors: 23

Best Nude Heels for All Skin Tones

Kahmune Becky Pointed Toe 70mm Pumps

Becky Pointed Toe 70mm Pumps
Best Nude Heels for All Skin Tones

Kahmune Becky Pointed Toe 70mm Pumps

Customization is key at Kahmune, which offers shoes in 10 different skin tone shades, and various heights from kitten to ultra-high. For comfort, this Becky Pump is a winner with its lower heel height and two layers of memory foam padding.

Heel Height: 2.75" | Material: Nappa Calfskin, Patent Leather, or Suede | Size Range: 4.5-13 | Colors: 10

Most Comfortable Heels for Summer

Dolce Vita Pilton Sandal

Pilton Sandal
Most Comfortable Heels for Summer

Dolce Vita Pilton Sandal

Now 40% Off
Credit: Dolce Vita

These Dolce Vita heels are playful and versatile enough for any summer event, and dozens of customers have written about their noticeable comfort. One reviewer wrote, "So comfy and cute, the square toe and funky heel make these extra fun. They don’t fall off at all when walking, and aren’t too tight at all. LOVE!"

Heel Height: 3" | Material: Recycled synthetic | Size Range: 5-12 | Colors: 3

Advertisement - Continue Reading Below
Most Comfortable Espadrilles

Yoox Organic Cotton Essential Wedge Espadrilles

On Sale
Organic Cotton Essential Wedge Espadrilles
Most Comfortable Espadrilles

Yoox Organic Cotton Essential Wedge Espadrilles

Now 25% Off
Credit: Yoox

These espadrilles come recommended by Board Certified Surgical Podiatrist, Dr. Nelya Lobkova. She notes that the straps "provide extra stability in the ankle as well as the awareness that the ankle is supported, allowing you to wear heels for longer." She adds that the chunky wedge also provides more stability for the ankle.

Heel Height: 3.9" | Material: Organic Cotton | Size Range: 5-11 | Colors: 5

Most Comfortable Heeled Mules

Tony Bianco Shae Mule

Best Seller
Shae Mule
Most Comfortable Heeled Mules

Tony Bianco Shae Mule

Credit: Tony Bianco

These best-selling Tony Bianco mules can easily be slipped on and have a padded leather footbed for support. Not only are they super comfy according to reviewers, they're also a sophisticated addition to any outfit given the eyelet and bow detailing.

Heel Height: 3.25" | Material: Suede, Leather | Size Range: 5-10 | Colors: 3

Headshot of Samantha Lawyer
Samantha Lawyer

Sam Lawyer is a lifestyle writer and television producer based in New York City. She’s been contributing to Woman’s Day for nearly five years, and covers a variety of topics from gifting, to health, and entertainment. Her work has additionally been featured in Cosmopolitan, Country Living, and Good Housekeeping. When she’s not writing or producing, you can find her binging her favorite Bravo shows or getting walked by her French Bulldog.

Headshot of Elizabeth Berry
Updates Editor

Elizabeth Berry (she/her) is the Updates Editor at the Good Housekeeping Institute where she optimizes lifestyle content across verticals. Prior to this role, she was an Editorial Assistant for Woman’s Day where she covered everything from gift guides to recipes. She also has experience fact checking commerce articles and holds a B.A. in English and Italian Studies from Connecticut College.

Fashion Tips

best couples halloween costumes 2023 the marvelous mrs maisel midge and joel and the barbie movie barbie and ken

80 Easy Couples Halloween Costume Ideas for Adults

best fall wedding guest dresses

20 Stylish Fall Wedding Guest Dresses

beautiful woman spending time in the city

The Best Fall Clothing on Amazon

a mother and daughter in matching swim suites running towards the ocean in costa rica

Where to Shop Cute Mommy & Me Outfits

Advertisement - Continue Reading Below
Advertisement - Continue Reading Below
Logo
twitter icon
youtube icon
facebook icon
instagram icon
pinterest icon
Hearst Lifestyle and Design Group - A Part of Hearst Digital Media

A Part of Hearst Digital Media

We may earn commission from links on this page, but we only recommend products we back.

©2023 Hearst Magazine Media, Inc. All Rights Reserved.

Privacy NoticeCA Notice at CollectionYour CA Privacy Rights/Shine the LightDAA Industry Opt OutTerms of UseSite Map
Cookies Choices