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The Most Comfortable Heels for Work

The Most Comfortable Heels for Work

Let’s talk about the Holy Grail of workwear: finding the most comfortable heels for work. 

The aching, sometimes blinding pain that comes with squeezing our feet into heels that don’t fit well, are too high, or are inherently uncomfortable is a choice I leave to the younger generation. 

After the pain of pregnancy, childbirth and generally just being a woman, I am done with self inflicted discomfort, thank you very much

And I know you are too because comfortable heels for work are one of the biggest topics of conversation here on the blog and over in our private Facebook group

This post to designed to serve as a resource that will be updated regularly. Save it, or “Pin” it so you can reference it as needed. It’s broken down by price point, with options in the under $100 range, $100 – $250 and a handful of “investment” heels at the over $250 plus mark. 

The Most Comfortable Heels for Work

Comfortable Heels for Work

Today we are focusing on a classic pump style heel. Within these recommendations, you’ll find not only a variety of price points but also heel heights and color choices. 

These are HEELS, I’m working on a similar post for flats and kitten heels. 

As always we want to hear from you so be sure to scroll to the bottom to add your favorite pick. As we gather comments we’ll add your picks to the post! 

Before we dive in, a note on price point. Just because a shoe is expensive doesn’t mean it’s going to be comfortable. I find many of the high designer brands are brutal on your feet.

Conversely, many brands that focus on comfort don’t always produce the most stylish shoe. Happily, there are a few options that we’ll cover below. 

This post if FULL of options for everyone. 

Most Comfortable Heels: Under $100 (ish)


Under $100 Comfortable Heels One, $90  |  Two, $75  |  Three, $110
We’re calling this under $100 ish because when these go on sale they are well under $100. 
Via Spiga makes a nice heel at a reasonable price point.  They are not exactly designed to be comfortable, but the solid construction, and walkable heel put them on the top of my lists. This simple pump has a 2 1/2″ heel and are on sale at Nordstrom Rack for $90. 
The Nine West “Flax Pointed Toe Pump” are a fantastic option, currently on sale for $56 with checkout code YAY at Macy’s. They come in a wide array of colors and prints to accommodate any style or void in your wardrobe. 
A reader favorite are these stylish pumps by Naturalizer. For years, I found their heels to be frumpy, but these are fabulous! They are sleek and sophisticated – with certain colors on sale for under $70. 
Another Naturalizer option is the Gia Pump, in a kitten style for under $60. 
A personal recommendation on the comfort brand front, are these LifeStride pumps.
Last November I ran my kids school’s auction night. It’s a big deal, a ton of work, and required me on my feet for the entire day of. The theme was 80s and instead of creating a costume that let me wear sneakers (that would have been smart) I went as Joan Collins from Dynasty.
Admittedly, I was a major snob about these, but since I needed a pump for my look I reluctantly purchased them. They were so comfortable. I managed all day, and danced well into the early morning in them without any discomfort at all. 

Most Comfortable Heels: $100 – $250

Mid Range Comfortable Heels Top to Bottom: One, $118  |  Two, $137  |  Three, $120  |  Four, $128 
In the mid $100 – $250 range you’re going to get a high quality shoe that will elevate your outfit. 
The Banana Republic 12 Hour Pump is a rockstar heel. They are classic available in 18 (!!!) colors and finishes, ranging from neutrals, to animal prints and snake skins, to poppy and bold colors. They frequently go on sale. Standard retail is $130, and right now there are a few colors as low as $40. 
Another Via Spiga Option is their Nikole Pump. It has a higher heel than the first option, but just as well made and comfortable. Sizes and styles are limited here, which makes me wonder if they are phasing them out, but still worth giving a try if you want a stiletto style that you can walk in. 
If you have been on this site for any length of time, you know I love Sam Edelman. From pumps to boots they are my favorite. The quality is outstanding and the price doesn’t break the bank. Their Hazel pump is my go-to for the color options and widths.
You can buy these in Medium, Narrow and Wide. I personally wear these all the time and never have an issue with comfort. 
Rounding out our mid range options for comfortable heels are Ann Taylor pumps. This is another personal recommendation. Their Eryn pump is gorgeous. With a simple 2 1/2″ heel, in a lovely suede finish, these would be beautiful with a formal suit, or more dressy business attire. 

Most Comfortable Heels: $250 +

Designer Comfortable HeelsOne, $299  |  Two, $398  |  Three, $595
Finally, let’s talk about investment shoes since they are not known for being the most comfortable. 
Price point is personal and our site has an incredibly diverse range of readers. 
Personally, I’ve worn many designer heels and find them to be terribly uncomfortable. Louboutins I can’t even stand in, let alone walk. I wore (tried to wear)  a pair my husband bought me on time in Vegas. I looked like a drunk call girl stumbling around the casino. 
When I got home I sold them on Poshmark. 
Manolo’s are like walking on cardboard, $500 + cardboard, and they are cut so narrow I look like Cinderella’s step sister. 
But a few pairs actually delight me. 
Clients swore by Paul Green shoes back in my personal shopping days. Designed with comfort in mind, these “cup” your feet so they are snug on purpose. They are another 2.5″ heel you can last all day in. 
Stuart Weitzman was another go-to. These a beautiful, not quiet 3″, and of course go with everything.  
Finally, my pick for where to spend without being disappointed are these Jimmy Choo pumps. I’ve worn these for years. They are not comfortable heels as in you’re walking on a cloud. Rather, they feel solid, and sturdy, like you stomp around in them all day with no problems.
I get them professionally cleaned and resoled once a year and they look like new. If you are into high quality over quantity you can’t go wrong with these.  

Readers Tell Us Their Favorite Heels

Crowd sourced from our comment section

Sarah Flint Perfect Pump

Clarks Adriel Viola Pump

L.K. Bennett Pump

Anne Klein Finn Pump

Cole Haan Grand Ambition Pump



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Recommendations are based on my experience as a personal stylist and wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail. 

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The Most Comfortable Heels for Work

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Friday 7th of February 2020

That is great info on the toe box , you’re SO right ! I was just comparing a pointy pair of Anne Klein’s that I have had for years , which do not hurt at all , with a new pair of Alfani step n flex pumps , I just bought from Macy’s. Assuming they would be Uber comfortable based on the cushioned footbed and rubber soles .., BUT , i didnt have enough room between the big toe and the pointy tip , so they squeeze my toe towards the toe box and hurt ... going back ! Thank you for decoding the misconception !

Megan Kristel

Monday 10th of February 2020

So glad that was helpful!


Wednesday 29th of January 2020

My favourite brand, bar none, is Roberto Capucci. I have pairs that date back to before my first child was born in 1987! With regular care and maintenance they may well outlive me! My most recent pair purchased in 2019, the Mary in a nude patent were purchased for said child's wedding. At $279 Canadian I find they are a very reasonable price for the quality.


Sunday 26th of January 2020

I love Sarah Flint's Perfect Pump. Sexy looking for work or a night out.

Desiree Campbell

Friday 3rd of January 2020

Two of my favorites for the office - 1. Clarks Adriel Viola Pump ( 2. Franco Sarto Frankie Wedge ( I have these in nude, black and leopard and always get compliments:)

Mrs. Todd

Friday 10th of May 2019

I love the BR Madison Pumps. The colors are gorgeous, and they are comfortable. I especially like the nude suede as a neutral.

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