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
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.
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.
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.
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.
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.
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.
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.
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.
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.
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