This post on comfortable work shoes is part of The Five Must-Have Pieces for Your Work Wardrobe series.
Fashionable, comfortable work shoes are not an oxymoron. I (Lani) always say I’m the only fashion stylist who won’t make you wear high heels. However, I will make you wear a cute flat that elongates your leg line and aligns with the silhouette of your pants or skirt. Get the shoe silhouette right, and your whole outfit will look and feel balanced. Get the shoe wrong, and your whole outfit looks off. Flats too flat? You may look like you are standing in a hole. It’s not a pretty vision, yet we see it a lot!
You can look cute and be comfortable. We swear. It just takes a little patience. We’ve done most of the hard work for you by finding the cute yet comfortable work shoes. Now, all you have to do is add them to your cart!
Happy Shopping!


Lani in her new Ally Mary Jane Slingback Kitten Heels c/o Ally.
Pumps
This year, we’ve really narrowed down the shoe brands we’re recommending to the most comfortable and noteworthy ones. Ally will always be at the top of that list. Their Lower Block Heel is a timeless work pump, but our favorite newcomer to their heel inventory is the Mary Jane Slingback Kitten Heel. Slingbacks are a great trick for people with oddly small heels (like Lani!), who can have trouble not walking out of regular pumps and flats.
The arch support and padding in Ally Shoes are unlike any you’ve previously experienced in a heel. Plus, they come in four widths: narrow to extra wide. Use the code RLS10 to get 10% off your first order.
If you’re looking for something at a lower price point, we found many great Naturalizer pumps this year. Naturalizer is a tried-and-true comfort brand. Most of their styles come in a wide variety of colors and widths. Browse below to find your favorite comfortable pump!
Ally Shoes Lower Block Heel, $335 (also available in a 3-inch Block Heel Pump, $335)
Ally Mary Jane Slingback Kitten Heel, $355
Gentle Souls by Kenneth Cole Gardena Pointed Toe Pump, $189
Margaux The Cluny Slingback, $345
Naturalizer Maddox Ankle Strap Pointed Toe Pump, $148
27 Edit Naturalizer Elaine Slingback Pointed Toe Pump, $170
27 Edit Naturalizer Francis Pump, $145
Sarah Flint Perfect Emma, $495
Vivaia PointEase™ Slingback Heels, $159
Flats
We get it. Not everyone is comfortable in pumps all day. The good news is that you can find a comfortable, stylish flat to replace a pump for work. “Flats” can cover a wide range of shoe styles, so we kept it classic with simple ballet flats, Mary Jane flats, and slingbacks. Hopefully, this succinct list of the best options will help you narrow your choices! Be sure to check the links for multiple color and width options in several of these shoes. For something with a little flair, we love the Bared Mountaingem slingback shoe. And for a dainty, classic flat, the Sarah Flint Natalie is currently available in all the classic colors, plus some fun seasonal options.
Ally Shoes Mary Jane Forever Flat, $255
27 Edit Naturalizer Carla Flat, $140
Sarah Flint Natalie Sling, $375
Scarlett Chase Belle Ballet, $405
Vionic Alameda Mary Jane Flat, $155
Loafers
At RLS, loafers are among our favorite shoe styles. They offer more structure than a flat and can dress up or down an ensemble. Loafers are trending a little more casual this year than in the past, but with the casual look comes even more comfort. And no one has ever complained about that. They can also be an easier fit than flats for our small-heeled friends. The Ally Suede Penny Loafer is made from lambskin suede leather and genuinely feels like butter on your foot.
If you’re in need of a super travel-friendly loafer, try the Vivaia Square-Toe Icon Loafers, which are breathable for all-season wear and machine washable. We love an easy-care shoe!
Margaux The Marlowe Loafer, $385
Quince Italian Suede Penny Loafer, $84
Vivaia Square-Toe Icon Loafers, $129
Mules
Many clients have turned to mules for their work wardrobe. Why? They’re chic, comfortable, and the perfect shoes to choose during those tough seasonal transitions when it’s neither warm nor cold. We were very selective with our mule choices this year, choosing only the options that really elevate your work look. Some mules tend to look more casual, but the Inez Bea and the Scarlett Chase Audrey 55 Pump are incredibly stylish and elongate the leg with their pointy-toe shapes. For a flat option, The Clara comes in suede and leather, as well as other fabric options.
Scarlett Chase Audrey 55 Pump, $595
What is your favorite comfortable work shoe? Do you prefer pumps vs. slingbacks? Loafers vs. flats? Have you tried any of these suggestions? Let us know in the comments below!
Real Life Style is a style consulting firm that teaches busy women to wear their power so they can live their lives fully and confidently. Lani Inlander, Kyle Dunphy and Sloane True are based in the Washington, D.C., metropolitan area and serve clients nationwide. We offer personal styling services, and an on-demand e-course.
Once in a while, you can find Lani Inlander and Real Life Style on Facebook, LinkedIn, Pinterest, and Instagram. Mostly, they are happily busy serving their fabulous clients, not hanging out online!































Thank you so much for the great shoe ideas. I appreciate the prices being listed.
Our pleasure!
You answered my unasked question about Clark’s shoe stores — I was looking in the malls with no success — a loss for me and my wide feet for sure.
I know! It is so frustrating, isn’t it? They do still have outlet stores though.
Love, love, that you listed shoes that come in a 4.5. I have a hard time finding shoes that are not black or nude and then are comfortable.
Which ones do you like?!
Very interesting article!
That Ally loafer is so chic! I want everything :)