Skip to Content

Every item on this page was chosen by a The Pioneer Woman editor. We may earn commission on some of the items you choose to buy.

20 Most Comfortable Work Shoes for Women That Are Also Super Cute

Cute and comfy are not mutually exclusive.

Headshot of Macie ReynoldsBy Macie Reynolds
best comfortable work shoes for womenpinterest icon
everlane / vivaia

If anyone knows the importance of comfy shoes, it's Ree Drummond. The Pioneer Woman is always on the go—chasing after her dogs, standing for hours in her kitchen to film her Food Network show, and roaming around Drummond Ranch. Take all of that into account and it's only natural that her favorite pair of shoes (after cowboy boots, of course!) is a pair of On Cloud Running Shoes. But sadly, sneakers don't always cut it. Sometimes, you need to take your go-to footwear to the office—which is where these comfortable work shoes for women come into play!

Our Top Picks

  • 1
    Clarks Giselle Cove Slingback Platform Wedge Sandals

    Best Wedge

    Clarks Giselle Cove Slingback Platform Wedge Sandals

    $59 at Macy's
    Read more
  • 2
    Gessica Ballet Flats

    Best Ballet Flat

    Gessica Ballet Flats

    Read more
  • 3
    The Slingback
  • 4
    Dansko Professional Clog

    Best Clog

    Dansko Professional Clog

    Read more
  • 5
    Seychelles Lock and Key Mary Jane Heels

    Best Mary Jane Heels

    Seychelles Lock and Key Mary Jane Heels

    Read more

Ahead, we've curated a list of the absolute coziest, most cloud-like options on the market. And no, we're not going to ask you to sacrifice style for comfort. Heck, several of the options we've provided are cuter than some of the non-comfy shoes we've seen! Sleek styles, fun patterns, two-tone color schemes, and printed floral designs will make you forget what you thought you knew about orthopedic (and orthopedic-adjacent) shoes. But first, you'll have to decide what you're looking for: Is a wedge heel appropriate for your workplace? How about a pair of fall-ready ankle boots? Or you can go with classic comfortable flats! Whatever it is you're after, we've likely got an option here for you—and then some.

1
Best Wedge

Clarks Giselle Cove Slingback Platform Wedge Sandals

Clarks Giselle Cove Slingback Platform Wedge Sandals
1
Best Wedge

Clarks Giselle Cove Slingback Platform Wedge Sandals

Now 40% Off
$59 at Macy's
Credit: Macy's

Cushioned footbeds and adjustable slingback straps make these wedge sandals as comfy as they are cute. They come in three neutral colors or a bright red hue to really make a statement!

2
Best Ballet Flat

Gessica Ballet Flats

Gessica Ballet Flats
2
Best Ballet Flat

Gessica Ballet Flats

Now 64% Off
Credit: Easy Spirit

Not only are these flats affordable and fashion forward but you can also ensure a perfect fit because they come in medium, narrow, wide, and extra wide widths. Plus, the faux patent leather toe and heel adds an extra touch of glamour.

3
Best Convertible Heel

The Slingback

The Slingback
3
Best Convertible Heel

The Slingback

Credit: Pashion Footwear

A heel that converts to a flat? It sounds almost too good to be true—and yet it is! You can even choose between block or stiletto heels.

Advertisement - Continue Reading Below
4
Best Clog

Dansko Professional Clog

Dansko Professional Clog
4
Best Clog

Dansko Professional Clog

Credit: Nordstrom

If you're on your feet all day at work, you're probably going to want to stay away from heels. These stylish clogs feature a cushy footbed and anti-fatigue rocker midsole for true all-day comfort.

5
Best Mary Jane Heels

Seychelles Lock and Key Mary Jane Heels

Seychelles Lock and Key Mary Jane Heels
5
Best Mary Jane Heels

Seychelles Lock and Key Mary Jane Heels

Credit: Anthropologie

Mary Janes truly never go out of style—and these days they're more comfortable than ever. The stacked leather heel on this pair makes them equal parts preppy and edgy.

6
Classic Choice

Aerosoles East Side Loafer

Aerosoles East Side Loafer
6
Classic Choice

Aerosoles East Side Loafer

Credit: Aerosoles

This brand prides itself in creating shoes with innovative features that guarantee comfort—and this pair is no exception. Along with that sleek look and stylish low heel, they also have a memory foam padded footbed and a signature diamond flex outsole.

Advertisement - Continue Reading Below
7
Best Heeled Option

Vivaia Melody 2.0 - Running Heels

Vivaia Melody 2.0 - Running Heels
7
Best Heeled Option

Vivaia Melody 2.0 - Running Heels

Now 14% Off
Credit: Vivaia

Who says you can't run in heels? It's literally in the name of these. So, they'll definitely get you through the work day. That's thanks to a dual-layered foam support system, arch comfort on the insole, a patch to keep blisters away, and anti-slip outsoles. They're also breathable and deodorizing. And did we mention that super chic square toe and chunky heel look?

8
Best Loafer Option

Naturalizer Adiline Loafer

Naturalizer Adiline Loafer
8
Best Loafer Option

Naturalizer Adiline Loafer

Credit: Naturalizer

It hardly gets more classic than wearing a loafer to the office. This ultra lightweight pair will certainly get the job done with Contour+ Comfort technology that offers a premium fit and all-day comfort with a flexible EVA sole and non-slip lug outsole. They're even available in tough-to-find sizes and widths.

9
Best Budget Option

Knit Almond-Toe Ballet Flats

Knit Almond-Toe Ballet Flats
9
Best Budget Option

Knit Almond-Toe Ballet Flats

Credit: Old Navy

The exterior here is a soft, stretchy textured knit, and the interior is lined with—get this—memory foam. Oh, and they're only $35. We have a winner!

Advertisement - Continue Reading Below
10
Elasticized Back

Everlane 'The Day' Heel in Bone

Everlane 'The Day' Heel in Bone
10
Elasticized Back

Everlane 'The Day' Heel in Bone

Credit: Everlane

There's something positively special about this two-tone color scheme. The manufacturer claims you can walk in these heels all day long, and there's an elasticized back for added comfort.

11
600+ Reviews

Rothy's The Square Mary Jane

Rothy's The Square Mary Jane
11
600+ Reviews

Rothy's The Square Mary Jane

Credit: Rothy's

With flats this sophisticated, who needs heels? We love the soft, cloud-like comfort of this Rothys pair, and its chic square toe and flexible strap. You can also find it in a pointed toe style.

12
Best Pointed Toe Option

Women's Zala Pointed Toe Pumps

Women's Zala Pointed Toe Pumps
12
Best Pointed Toe Option

Women's Zala Pointed Toe Pumps

Credit: Bloomingdale's

Sleek, modern, and thoroughly stylish, these true-to-size pumps hardly look like the "comfy shoes" we've come to know. The block heel adds extra comfort, while the pointed toe imparts an air of elegance.

Advertisement - Continue Reading Below
13
Cute and Practical

Naturalizer Bay Heeled Boot

Naturalizer Bay Heeled Boot
13
Cute and Practical

Naturalizer Bay Heeled Boot

Credit: Zappos

When fall comes along, you're going to want a boot you can count on. This waterproof pair, which features a side-zipper closure and flexible rubber outsoles, will get you through the bad weather and look cute under your desk.

14
No-Slip Sole

Birdies 'The Blackbird' Flats

Birdies 'The Blackbird' Flats
14
No-Slip Sole

Birdies 'The Blackbird' Flats

Credit: Birdies

The herringbone pattern on these woven raffia flats is too cute and reminiscent of vintage styles from decades ago (in a good way!). A no-slip rubber sole gives them added traction.

15
Ree's Style

The Pioneer Woman Embroidered Ballet Flats

The Pioneer Woman Embroidered Ballet Flats
15
Ree's Style

The Pioneer Woman Embroidered Ballet Flats

Credit: Walmart

A slight heel gives these ballerina flats a little extra support, while the faux leather is soft and offers a nice amount of give. Of course, we're most smitten with that floral design. 😍

Advertisement - Continue Reading Below
16
Soft and Stylish

Birdies 'The Vesper' Loafer

Birdies 'The Vesper' Loafer
16
Soft and Stylish

Birdies 'The Vesper' Loafer

Credit: Birdies

Everyone needs one good pair of loafers, and this buttery soft pair is an excellent choice. The suede molds to your feet for a "hug-like fit," according to the manufacturer.

17
300+ Reviews

Margaux 'The Heel'

Margaux 'The Heel'
17
300+ Reviews

Margaux 'The Heel'

Credit: Margaux

Looking for an elegant block heel that won't give you blisters? Look no further. This versatile pair comes in a few different patterns and is both comfy and utterly fabulous.

18
Popular Pair

Allbirds Women's Tree Breezers

Allbirds Women's Tree Breezers
18
Popular Pair

Allbirds Women's Tree Breezers

Credit: All Birds

You know you can trust Allbirds for a comfy shoe, and these Tree Breezers do not disappoint. They're made of lightweight, breathable eucalyptus fiber, and the collar is ribbed for a streamlined fit.

Advertisement - Continue Reading Below
19
Best Vegan Option

Birdies 'The Starling' Loafer

Birdies 'The Starling' Loafer
19
Best Vegan Option

Birdies 'The Starling' Loafer

Credit: Birdies

Vegan materials, a no-slip sole, and a fluffy velvet fabric make these shoes a must-have. We love the inviting, textured look of the shoe pad.

20
Best Sneaker Option

Rothy's The Original Slip On Sneaker

Rothy's The Original Slip On Sneaker
20
Best Sneaker Option

Rothy's The Original Slip On Sneaker

Now 17% Off
Credit: Rothy's

If you want to go for a casual feel, these slip-ons are your best bet. They're supportive and stylish with no break-in period and nine colors and patterns to choose from—and all without the headache of zippers and laces. You can even throw them in the wash!

Headshot of Macie Reynolds
Macie Reynolds
Assistant Editor

Macie Reynolds is the assistant editor of E-Commerce and SEO for The Pioneer Woman.

Your Ultimate Shopping Guide

pioneer woman labor day sale

Shop Epic Deals on Ree's Line During Labor Day

walmart labor day sale 2023

Don't Miss Out on Walmart's Labor Day Sales

best photo gifts

21 Unique Photo Gifts That Everyone Will Love

best stadium seats

The Most Comfortable Stadium Seats for Game Day

Advertisement - Continue Reading Below
Advertisement - Continue Reading Below
Logo
twitter icon
facebook icon
instagram icon
pinterest icon
A Part of Hearst Digital Media

A Part of Hearst Digital Media

We may earn commission from links on this page, but we only recommend products we back.

©2023 Hearst Magazine Media, Inc. All Rights Reserved.

Privacy NoticeCA Notice at CollectionYour CA Privacy Rights/Shine the LightDAA Industry Opt OutTerms of UseSitemap
Cookies Choices