The Most Comfortable Heels You Can Actually Walk In (2020)


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The Most Comfortable Heels 2020

Just because many of us are still fully in “work from home” home mode doesn't mean we still can't benefit from the most comfortable heels! 

For some of us, outdoor client meetings – also known as boozy lunches – are starting to pick back with acceptable social distance guidelines. 

For others, the only way to fully embrace the WFH home environment is to act like you're actually going into the office, which means perfecting everything from the highlights right down to the heels! 



Keep reading for reviews of each, or pin this article to save it for later ⇟ 



The Most Comfortable Heels for Work (2020)

There are a couple brands in particular that focus on the right blend of comfort, fashion, and durability. Below, we've chosen our favorite styles that are both comfortable and appropriate for work, dressy events, date nights or any occasion!


Most Comfortable Heels Brands


 Read more:  The Best Travel Shoes 2020: Comfy + Stylish





Most Comfortable Heels!


Most Comfortable Block Heels: Steve Madden

When it comes to the most comfortable designer heels, look no further than the Steve Madden Block Heeled Sandal

The nubuck leather upper, thin buckled ankle strap, and 3.25″ heel provide all the chic flair you would expect from a brand like Steve Madden

More importantly, though, the padded foot bed, wrapped block heel structure, and rubber outsole offer the comfort, traction, and durability to feel great – and look even better! 

Looks great with: a flowing solid-red dress, or blue denim jeans and a red top! 

Steve Madden Declair Block Heeled Sandal

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Check the latest reviews and see all color options here


Most Comfortable Pumps: Nine West 

Nine West is a standard bearer of the most comfortable women's heels, and their classic Flax Pump is no exception! 

While we prefer the classic black pictured above, the Flax Pump comes in a dizzying array of 15 colors available in both leather and synthetic  fabrics. 

The pointed toe adds a touch of sophistication, and the man-made cushioned foot bed ensures your 2 little dainties stay safe and comfortable! 

Looks great with: black jeans and pretty much any chic top! 

Nine West Flax Pump

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Check the latest reviews and see all color options here



Most Comfortable Heels for Wide Feet: Comfortiva 

It would be some kind of cruel irony if “Comfortiva” wasn't churning out the most comfortable women's heels, right? 

Fortunately, these block sandals don't disappoint!

These are some of the most comfortable heels for wide feet, as the Comfortiva sandals are sold in sizes up to a EE width! 

Additionally, the synthetic lining provides blister resistance, the polyurethane outsole ensures lightweight durability and traction, and the patented Pillow Top foot bed absorbs pressure and offers additional comfort! 

Looks great with: colorful denim or linen shorts! 

Comfortiva Neima Sandals

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Check the latest reviews and see all color options here


Most Comfortable Strappy Sandal: Blue by Betsey Johnson 

Let's not get it twisted. These embellished heels from Blue by Betsey Johnson exist first and foremost so you can make a statement!  

The satin upper, buckled ankle strap, and rhinestone embellishments are all there to ensure everyone else knows that you..have…ARRIVED! 

We love these heels because they make a fashion statement without leaving statements (in the form of blisters and bruises) on your feet, as the lightly padded foot bed and modest 2.25 inch heel combine for a comfortable and fashion-forward heel! 

Looks great with: whatever you're wearing to your next “white out” party. White dress, white jeans, white crop top, whatever! 

Blue by Betsey Johnson Mel

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Check the latest reviews and see all color options here



Most Comfortable Wedge: Toms 

At first glance, the rustic Toms Cutout Sandals may appear charming without looking particularly comfortable. 

However, looks can be deceiving, and this couldn't be further from the truth! 

The Toms sandals feature a side zip for comfortable putting on and taking off, a durable, no-slip synthetic outsole, and a comfortable leather insole with bacteria-fighting treatment. 

Plus, as with all Toms shoes, each purchase gives a new pair of shoes to a child in need, meaning you can feel good while you look good, too! 

Looks great with: a gorgeous floral sundress! 

Toms Majorca Cutout Sandal

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Check the latest reviews and see all color options here


Most Comfortable Stiletto: Sam Edelman 

Using comfort and stilettos in the same sentence?! 

Yup, the Sam Edelman stilettos – which are the most comfortable black heels we've come across – have made us do just that! 

Made with a variety of leather, textile, and synthetic uppers, these stilettos feature a comfortable slip-on construction, over 4 millimetres of extra cushioning, and a synthetic heel tap that provides additional support and stability! 

Looks great with: your favorite black dress! 

Sam Edelman Hazel Pump

Sold on Zappos

Check the latest reviews and see all color options here



 Read More   in my favorite Comfy Shoe series:


Most Comfortable Shoes

The Most Comfortable Flats EVER

The Most Comfortable Sandals for Summer

The Most Comfortable Heels (you can actually walk in)

Everlane Flats - These 5 Pairs are Extra Comfortable

OluKai Shoes: Sneaker & Sandal Review


Best Sneakers

The Best White Sneakers that Go with EVERYTHING

Cute Casual Sneakers to Wear Anywhere

The Best Slip On Sneakers


Cozy At Home Shoes

Comfy Slippers for Women

Comfy Mens Slippers


Travel Packing List

Best Travel Shoes for Women

The Essential Business Packing List

The Best Packing Cubes for a Perfectly Organized Bag

The Best Carry on Luggage for 2020


Designer Inspired

The Best Cap Toe Ballet Flats to Get the Chanel Look, for Less

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