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The 21 Most Comfortable Work Heels On Amazon

There's nothing like a great pair of heels to add a stylish, feminine element to your work-wear, whether you're the blazer and dress pants type or you have a job that allows you to be a bit more casual. But if you're on your feet all day, have a commute that involves walking, or are constantly running around, you've probably found yourself wishing for a more comfortable pair of heels. If you're arrived at this article hoping for just that, you're in luck, because these 21 pairs of the most comfortable work heels are stylish, sophisticated, and conveniently available on Amazon.

If you're new to shopping for clothes and shoes on Amazon, rest assured that their ever-expanding fashion marketplace now rivals the selection you'd find at your go-to department store. The only difference? Checking out only requires one click, and shipping is fast. Even better, some of the shoes on this list are eligible for Prime Wardrobe, which means you can test them out for up to seven days before committing to buying. If you don't love them, returns are free, and you only get charged for what you keep. And yes, if you already have a Prime membership, Prime Wardrobe is automatically included.

Whether you're looking for a pair of statement-making slingbacks, a chunky, cushioned bootie, classic pumps with arch support, or something else entirely, you'll find it on this list of the most comfortable heels for work, below.

1. Podiatrist-Designed Kitten Heels With Orthotic Support

Available in 13 colors and prints, these classic kitten heels come from Vionic, a brand whose shoes are designed to help relieve foot pain caused by plantar fasciitis and other similar conditions. The podiatrist-designed footbeds are made of soft, breathable microfiber, while added padding at the metatarsal dome offer enhanced support. With a small, 1.93-inch heel, they're also available in wide sizes.

  • Available sizes: 5-12 (including wide)

2. Statement-Making Slingbacks With A Tiny Heel

Add a touch of sparkle to your work-wear with these gorgeous Page pumps from Badgley Mischka. With cushioned insoles and a tiny (but sturdy) heel, these slingbacks provide a more comfortable alternative to your standard pair of flats or basic work heels. Get them in three colors: navy, beige, or light pink.

  • Available sizes: 5-11

3. A Timeless Pair Of Pumps That Come In 27 Colors & Prints

Though these heels are among the highest you'll find on this list, many shoppers swear by Sam Edelman's shoes when it comes to comfort. If you simply can't give up a high heel, you might find this pair more comfortable than most others on the market. And, since they're available in narrow and wide sizes, it'll be easy to find the perfect fit. Choose from a stunning selection of 27 solid colors and fun prints.

"No pinching despite the nice pointy toe," reported one reviewer. Another commented, "Surprisingly comfortable for a high heeled stilettos."

  • Available sizes: 5-12 (including narrow and wide)

4. A Simple Pair Of Low Pumps With Trademarked Orthotic Technology

For work environments with more traditional dress codes, these are the perfect pair of comfy, classic heels to keep in your closet. Available in black, beige, and navy, they'll go great with all your suits, skirts, and dress pants — though thanks to their simple, versatile look, you might wind up whipping them out for more formal occasions, too. Designed with Clarks' OrthoLite footbeds, they have multiple cushioned layers and are designed to mold to the shape of your feet.

"These barely felt like heels. They almost felt like flats. And zero damage or irritation to the back of my foot and my toes felt just fine," reported one reviewer.

  • Available sizes: 5-12 (including wide)

5. Of-The-Moment Booties With A Small Kitten Heel

Another great discovery from find., a brand known for their on-trend styles but affordable price tags, these booties will allow you to get in on two trends at once — kitten heels and croc-embossed leather — without sacrificing comfort. If you don't love the classic black (or, if you love them so much that you wind up wanting another pair), they're also available in a versatile snakeskin print.

  • Available sizes: 5-10.5

6. A Strappy Pair Of Pumps Designed For All-Day Support

Strappy yet sophisticated, this pair of pointed-toe Suki pumps uses LifeStride's Soft System technology to provide all-day support and comfort. Designed with soft, cushioned soles and a heel just under 3 inches, they're available in three colors (in wide sizes, too).

"Wore them Sunday with expectations of having sore feet. Happily surprised that from the time I put them on until I got home, no hurt feet," wrote one customer. "Very comfortable for standing and walking - comfortable for 6-8 hours at a time," commented another.

  • Available sizes: 5-11 (including wide)

7. A Classic Pair Of Knee-High Boots With A Low Heel & Orthotic Technology

With just enough of a heel to give you some added height, these are the perfect pair of fall/winter boots to pair with all your dresses, skirts, and fitted pants. Inside, you'll find Clarks's signature OrthoLite footbeds, which were designed with multiple layers of the brand's Cushion Soft cushioning, while the grippy soles and low, chunky heel round out the comfortable style.

8. Classic Slingback Pumps With A Chunky Block Heel

Simple, affordable, and stylish, this is one pair of heels you'll find yourself wearing way beyond the office. Available in two colors — black and red — they go with just about everything: trousers and skirts, dresses and suits (and jeans and denim cut-offs when you're off-duty). One Amazon reviewer even wrote, "They are so comfortable that I bought the second pair in black."

  • Available sizes: 5-10.5

9. Podiatrist-Designed Booties For All Day Comfort & Support

Vionic does it again with this sleek pair of Trinity ankle boots, which come in black and chocolate brown. Featuring cushioned, podiatrist-designed footbeds for all-day comfort and orthotic support, they have a low, chunky heel, zip closure, and sleek gold buckle detail.

"They fit true to size and so comfortable right out of the box. No break in time required," reported one reviewer. Another fan of the booties commented, "These are the most comfortable pair of boots I have ever owned. They have great support for my plantar fasciitis." Additionally, multiple reviewers noted that they fit true to size.

  • Available sizes: 5-11 (including wide)

10. A Playful Pair Of Kitten Heels For Lovers Of Bold Footwear

If you love to make a statement with your shoes, this playful pair of Kate Spade pumps combines a bold, flirty print with low-heeled comfort. Available in black and pink, both colors come adorned with adorable hearts and a feminine bow. "They are actually the most comfortable heels I’ve ever owned," reported one reviewer.

  • Available sizes: 5.5-8.5

11. A Pair Of Low, Chunky Pumps That Go With Everything

Another versatile shoe that you'll wind up wearing way beyond the office, these D'Orsay-style pumps have a low heel, pointed toe, and adjustable buckle closure. They come in 11 solid colors and prints, including beige, floral, and shimmery silver. 70% of reviewers gave them a perfect five-star rating, with dozens raving about how comfortable they are.

One reviewer commented, "These shoes are really comfortable and are perfect for work. You can wear these everyday because they're both dressy and casual at the same time. They're also perfect for when you want to wear a heel but you want to be able to move fast at the same time, since they aren't very tall and have ankle straps for added security."

  • Available sizes:

12. Open-Toe Booties With Podiatrist-Designed Footbeds

Another cute discovery from Vionic, these open-toe booties are perfect for work environments that allow you to dress a bit more casually. Like all of the brand's shoes, the footbeds, which are cushioned and lined with soft microfiber, were podiatrist-designed for maximum comfort. Meanwhile, the stacked block heel adds to their all-day wearability. Get them in three colors, including classic black and grey.

  • Available sizes: 5-9.5

13. A Minimalist Pair Of Sandals With A Thick Block Heel & Padded Footbeds

These mules have a low, block heel and padded footbed, which makes them comfortable enough to walk around in all day long. Inside, they're lined with super-soft microfiber, while their open-toe design keeps them breathable and cool. Get them in black, white, or red — multiple reviewers call them their "new favorite work shoe."

  • Available sizes: 6-11

14. A Simple Pair Of Booties Designed For Breathability & Comfort

Basic in the best way, you'll wind up wearing these simple Clarks booties from the office to date night and everywhere in between. The breathable, OrthoLite footbeds were designed to keep feet pain-free and cool, thanks to their multiple layers of cushioning and moisture-transporting technology. The supportive, 3-inch heel is thick and sturdy, the inside is soft, and the exterior leather is premium-quality. Asides from black, they're available in two shades of brown.

One reviewer, who has plantar fasciitis, raved, "These are the first heeled Clarks I purchased and I cannot believe the comfort. I haven't been able to wear a heel in almost a year and I can wear these all day no problem! I am a venue manager and on my feet walking around all day. Since I started wearing Clarks I have been pain fee! They are magic, they are beautiful, they are worth every penny."

  • Available sizes: 5-12

15. Over-The-Knee Vegan Suede Boots With Built-In Cushioning

Thanks to their cushioned padding and chunky heel, these over-the-knee boots will keep you warm and cozy during cold-weather commutes. Made of vegan suede, they come in three colors: black, brown, and taupe. They even have an impressively high 4.7-star Amazon rating. "They’re soft and comfortable and I can walk in concrete all day in them with no complaints - the thick heel is the ticket," reported one reviewer.

  • Available sizes: 5.5-11

16. Simple Low-Heeled Pumps That Are Professional, But Pretty

Simple and versatile, these classic, closed-toe pumps have an elegant, Parisian-chic vibe. Available in black, navy, and beige, they have a low heel that won't cause your feet to ache if you wear them all day long. "These are my new staple shoes! Super comfortable and perfect height heels for work. Only took a couple of wears to break in," commented one reviewer.

  • Available sizes: 5-10.5

17. Versatile D'Orsay Pumps With Soft, Cushioned Footbeds

Another great pair of D'Orsay pumps, this pair comes in statement-making leopard and snakeskin prints, too. Designed to be comfortable enough to walk in all day long, they have cushioned footbeds, slip-resistant soles, and a buckle closure to adjust to your ankle.

"I bought these shoes for my wedding day and I didn't break them in beforehand, but they were still so comfortable!" wrote one reviewer. Another commented, "The rubber sole aspect of the shoes are great too because they don't make that loud heel noise when you walk around in an office."

  • Available sizes: 5-11

18. A Durable Pair Of Booties For Rough Weather Commutes

These Timberland Camdale boots are perfect for anyone who has a commute that involves a lot of walking. That's because they're designed with ultra-durable soles, OrthoLite cushioned footbeds, and thick, textured heels that'll prevent you from slipping and sliding, even in the worst of weather. The collar at the ankle is padded to prevent chafing or tightness, while the multi-layer footbeds were designed to be breathable and antimicrobial. Though they'll definitely look cute with more casual ensembles, try pairing them with black tights under a dress or skirt to add a bit of military-inspired edge to your work-look. Get them in three colors.

  • Available sizes: 5.5-11

19. A Stylish Pair Of T-Strap Pumps That Reviewers Call The "Most Comfortable Shoes Ever"

Reviewers can't stop raving about how comfortable these shoes are. The sleek, T-strap design gives them a more stylish touch than your basic pair of pumps, and it's hard to think of an outfit they wouldn't look great with. Meanwhile, to ensure you stay comfortable and stable, the pumps were designed with traction technology on the soles, as well as a foot-conforming shape that slopes gently downwards. Get them in black, nude, and red, in leather or suede.

  • Available sizes: 5-11

20. Strappy, Low-Heeled Sandals With Podiatrist-Designed Footbeds

With their sleek ankle strap and open-toe design, you'd never guess these shoes were designed with orthotic support in mind. Available in black and brown, these sandals boast Vionic's signature podiatrist-designed footbeds and a low block heel for added stability.

One reviewer commented, "Love these shoes! Wore them 2 days in a row to work and they are extremely comfortable. Great heel height and cushioning. Love the Velcro as it makes them super adjustable!"

  • Available sizes: 7-10

21. A Lace-y Pair Of Kitten Heel Booties Designed With Comfort & Stability In Mind

With their lace-up look and skinny heel, these shoes probably don't look comfortable upon first glance. But they were in fact designed with cushioned footbeds, a soft, faux fur lining, and slip-resistant soles, making them the perfect pair of booties for staying chic and cozy in the cold weather. At under 2.5 inches, the heel is quite low, while the zip-up closure makes them easy to put on and take off. Get them in five colors and prints.

  • Available sizes: 5-15

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