Skip to Content

StarFREE! Wardrobe Checklist Download + Weekly Newsletter DOWNLOAD

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



Our Style Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers. 

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. 

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

If you enjoy our content and would like to help us grow, please  follow on Instagram and join our Private Facebook Group to access more advice and exclusive in-depth conversations with other like-minded women.

Learn about our mission to help women look and feel their very best, every day, here

Sign Up for Daily Content and Receive Our Free Classic Wardrobe Checklist



The Most Comfortable Heels for Work

Related Posts

 Join Megan Kristel for a comprehensive, 3 hour long, LIVE Virtual Workshop sharing personal style and shopping tips for women over 40 on March 31, 2023.


Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

Never Miss a Post

Enter your email address below to sign up for our newsletter and get your free copy of our Wardrobe Essentials Checklist sent to your inbox.

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.


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.

Tracy Baer

Friday 10th of May 2019

Thanks Megan for this post! This really will narrow down my search for badly needed new work appropriate pumps! I have 'bad' feet - a bunion on only one foot that has always been 1/2" larger (~7.5) than my other "normal" foot (~7) to begin with! So - sometimes I have to size up to a size 8 which is perfect for my "bad" foot - but then becomes way to large for my other foot (ugh!) Needless to say, I wish that I could try online ordering for some of these suggestions because I hate driving to Nordstrom.... I tend to run into DSW, but like you said, they don't always have the selection in-store - that you see on their website. I will do my best with these recommendations! Just wish that I had 'normal' feet - LOL!


Thursday 9th of May 2019

I find Ferragamo very comfortable in the high end category, L.K. Bennett in the mid category (and they tend to be more reasonable heels for both these).

Separately would love a roundup of stylish laptop bags and work bags for ladies who commute via public transport/walking and therefore carry it all a distance!

Megan Kristel

Friday 10th of May 2019

Thanks Jen. I use to have a few clients who LOVED Ferragamo, and agree, L.K. Bennett is also really wearable.

A laptop / workbag roundup is a great idea!


Thursday 9th of May 2019

This is my plan for Mother's Day: DSW, Nordstrom Rack (we don't have a Nordstrom anywhere close by), and a local family owned shoe store. I have my list and I will check back with what I get (fingers crossed!) I desperately need a nice nude pump for work that doesn't kill my feet!


Thursday 9th of May 2019

Thanks for the great information. This is a keeper. One to refer back to when shopping for shoes


Thursday 9th of May 2019

I like AK Anne Klein for wearable lower (1.5 “) heels that are excellent for work.


Thursday 9th of May 2019

I don't have to wear heels very often but, Cole Haan pumps are my go to when I do. I can stand in them all day without my feet hurting later.


Thursday 9th of May 2019

I honestly appreciate your attempt to round up a selection of professional looking albeit comfortable heels. However, it isn’t just the height of the heel that matters, as even some flat shoes are extremely uncomfortable. What usually lends comfort to a shoe is a wide enough toe box. The shoes you have featured all have pointed toes in the extreme. The exact opposite of a comfortable shoe. I clicked on your article in the hopes of seeing some decent looking almond toes. You must have such hammer toes to be able to wear the shoes you are featuring!

Megan Kristel

Thursday 9th of May 2019

Fun Fact: The shape of the toe box has little to do with the comfort of a shoe, though it's a popular misconception. However, the toe box needs to fit correctly, and that varies for each person. To prevent such things as blisters, corns and yes, hammer toe.

To ensure that a toe box, regardless of shape, fits well, we need a finger width distance between the top of our longest toe - which is usually our big toe and the toe box.

The fit issue actually comes with the ball of your foot fitting the sole of the shoe properly. If that is off, then your feet will slide into the tip of the shoe and no matter the shape of the toe, it will hurt.

If you prefer an almond toe and they work for you then great. You're welcome to recommend a brand that has been successful for you as that is the whole point to this post.

What I don't appreciate is the snark and condescending tone of this comment, as if I failed to provide helpful information.

And I'm not walking around with hammer toes, I'm too old to let style trump comfort.


Thursday 9th of May 2019

Thank you for this post! Your recommendations are always spot on. Would love to see more like it!

I have a pair of Sam Edelman D'orsay pumps that are a mid-height heel, super comfortable, and a little sexy (but still work appropriate) because of the D'orsay style. They ran me abut $120.

Micheal Micheal Kors also has a "flex" technology in their pump that makes them pretty comfortable as they aren't too stiff. You can get them on sale for under $100.

Megan Reister

Thursday 9th of May 2019

I'm also a Stuart Weitzman fan. I buy them from off-price retailers like Nordstrom Rack, Hautelook and Rue La La so that they are a little more affordable. Excited to see that DSW carries them.

Megan Kristel

Thursday 9th of May 2019

I was too! I forget to check online for better brands there, I tend to just run into the store and am always underwhelmed.


Thursday 9th of May 2019

When I wore heels on a regular basis, I was ALL IN on the Nine West pumps. I'd wear out one pair and immediately buy another. Very little breaking in necessary. My feet even survived a bachelorette party in Vegas wearing those heels!

Megan Kristel

Thursday 9th of May 2019

I feel the same way about Nine West. There just a good, solid shoe. And you sound like you managed better in Vegas than I did!

Heather Medina

Thursday 9th of May 2019

I work in event planning and attend many standing networking events. My favorite heels are from Rockport. They have kitten heels and a little higher. Once during an event "crisis", I had to run down the street and I might as well have been in sneakers.

I also wear a lot of Naturalizer heels.

I can usually get both for under $100 on sale.

Megan Kristel

Thursday 9th of May 2019

That's a fabulous endorsement!


Thursday 9th of May 2019

I'm a huge fan of Banana Republic's Madison 12 hour Pump. They are very comfortable, even for such a high heel. They have many colors each season, and you can always buy them on sale! (Actually, Banana has sales so frequently that you should never buy anything full price there).

Megan Kristel

Thursday 9th of May 2019

I forgot they were your favorite!