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Work Wardrobe

Fashionable, Comfortable Work Shoes

This post on comfortable work shoes is part of The Five Must-Have Pieces for Your Work Wardrobe series. 

Kyle in comfortable, work shoes

Kyle matching with Daisy in her Ally Suede Pumps in Blissful Blush

Comfortable work shoes are not an oxymoron. As Kyle proves in the picture above, the correct shoe can be the glue that holds a stylish outfit together. Get the shoe correct, and the silhouette is just right. But if you get the shoe wrong, the whole outfit looks off. Flats too flat? You may look like you are standing in a hole. Not a pretty vision, yet something we see all the time!

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. You can look cute and be comfortable. We swear. It just takes a little patience. Kyle and I have done most of the hard work for you, finding the cute but comfortable work shoes. Now all you have to do is add them to your cart!

Happy Shopping!

Ally Shoes

One of the best moments of my job as a personal stylist is when clients experience the simultaneous style and comfort of Ally shoes for the first time. This is arch support and padding unlike any you’ve previously experienced in a heel. Get 10% off your first order with the code RLS10.

The black suede lower block heel is our recommended starter pair. This elongating style, whether in the 2 inch or 3 inch version, is versatile enough to go from work to cocktail. Another favorite style of mine is the patent leather cap toe flat. I love the bossy beige leather and black combo worn with jeans or cropped black pants. And the new black leather bold block ankle boots are the comfortable heeled boots of my dreams!

Ally Shoes Black Suede Lower Block Heel

Ally Shoes Black Suede Lower Block Heel, $325, also available in a 3 inch Ally Shoes Black Suede Block Heel Pump, $325

Ally Bossy Beige Leather with Black Patent Leather Cap Toe Flat

Ally Bossy Beige Leather with Black Patent Leather Cap Toe Flat, $245

Comfortable and Fashionable dress shoes for work for Real Life Style, Ally leopard print block heels

Ally Fierce Leopard Haircalf Block Heel Pump, $325, also available in a 2 inch Lower Block Heel, $325

Ally Black Leather Bold Block Ankle Boot

Ally Black Leather Bold Block Ankle Boot, $475


AGL has a cult following for their chic, comfortable shoes. We are not huge fans of their popular rounded cap-toe ballet flat style for wearing to work. However, we do love their well-made pumps, pointed-toe flats, and loafers for the office. If you are willing to spend the money, these shoes are worth it!

AGL Mara Loafer are comfortable work shoes

AGL Mara Loafer, $399


Kyle and I have been so enthusiastic about Birdies shoes over the last few years, you would think they are paying us to advertise for the brand! We promise they are not. It is just that we have seen clients struggle to find truly comfortable (but cute!) flats and casual sneakers for years. Birdies has nailed it. Now if only they would keep our favorite styles in stock!

Birdies Heron Loafers, $130

Birdies Goldfinch Flats: women's work shoes

Birdies Goldfinch Flats, $150


Clarks has become a go-to for clients who need comfort but don’t want to sacrifice style in both the work and casual shoe categories. As with a lot of comfort brands, the styles range from fashionable to downright orthopedic. Do not get confused! Unfortunately, there are no longer any local stores in DC. However, you can still find Clarks shoes at department stores and online.

Stay tuned to Clarks’ line for Spring 2024. This is when you’ll start seeing shoes from Martine Rose, Clarks first ever guest creative director.

Clarks Sarafyna Iris Black Leather comfortable work shoes

Clarks Sarafyna Iris Black Leather, $110

Cole Haan

Cole Haan has long been a staple for our male and female clients who are looking for fashionable and comfortable work shoes. Unfortunately, this is another brand that has closed their local stores. And mostly stopped carrying wide shoes. (Grrrr!!!!)

Cole Haan Grand Ambition Pump in Amphora Leather

Cole Haan Grand Ambition Pump in Amphora Leather, $180

>Grand Ambition Slip-On Loafer for women

Grand Ambition Slip-On Loafer, $188


Believe it or not, clogs are not the only comfortable work shoe that Dansko makes. I’m kind of obsessed with their Larisa Flat. This versatile, fashionable, style comes in more colors than any of the comfortable work shoes in this entire post!

Dansko Larisa Flat women's work shoes

Dansko Larisa Flat, $125


Everlane makes really modern, designer-looking shoes for a decent price. The Day Gloves are popular for a more casual look with a slim pant or skirt. Collectors can’t stop at just one pair, as they come in some really fun colors. Recently, we’ve been loving their take on the Ballet Flat, which seems to have a more substantial sole than the Day Gloves . Lani is really trying not to hit “add to cart” over here!!!

Everlane The Italian Leather Day Ballet Flat, $145

Marc Fisher

The Marc Fisher Zala pump has been some of our clients’ favorite shoes for a few years. We’ve had clients buy fun seasonal colors and textures like boucle and snake, as well as the basics—black and navy leather. If the Marc Fisher Zala pump is your fit, don’t limit yourself to just one pair!

Marc Fisher Zala Pump

Marc Fisher Zala Pump, $160

M. Gemi

Have you braved the mule trend at work yet? If not, try the M. Gemi The Sacca Donna Mule with a skirt or pants. The M. Gemi Serafina Flat comes in multiple fun colors, but the black is our favorite because of how chic it looks!

M. Gemi The Sacca Donna Mule: women's work shoes

M. Gemi The Sacca Donna Mule $278

>M. Gemi The Serafina Flat: comfortable work shoes

M. Gemi The Serafina Flat, $298


Naturalizer has really stepped up their fashion game in recent years. Their True Colors Banks Slingback Pump comes in a full range of skin tone shades. Click through to find your match. But if you’re looking for a pop of color, check out the great seasonal colors, too!

Naturalizer True Colors Banks Slingback Pump, $100

Sam Edelman

We love Sam Edelman’s Classic Black Meadow Ballet Flat with a square toe. And if you’re like us and don’t like charms on your shoes, these are easy to remove.

Sam Edelman Meadow Ballet Flat

Sam Edelman Meadow Ballet Flat, $130

Sam Edelman Linnie Mule

Sam Edelman Linnie Mule, $140


Vaneli is a brand similar to Clarks. They have a mix of styles for a mix of customers. These Karida loafers really look like they could be on a shelf at Brunello Cucinelli, but for a fraction of the cost! And the Darrie pumps are great for anyone with sensitive feet or bunions.

Vaneli Karida women's loafers

Vaneli Karida, $175

Vaneli Darrie women's pumps

Vaneli Darrie, $165


These silver Vince Pointed Toe Loafers have become a client favorite as a dressy shoe. Don’t worry, they also come in black and tan for your less adventurous days!

Vince Camuto Becarda Pointed Toe Loafer

Vince Camuto Becarda Pointed Toe Loafer, $111


Vionic is a true comfort brand, specializing in plantar fasciitis and over-pronation. For some clients with severe back or foot issues, Vionic is a life saver. They have every style from sneakers and flip-flops to heels, loafers, and boots. The Vionic Sellah style below also comes is stunning and expensive looking in a very soft black leather too.

Vionic Mizelle Loafer

Vionic Mizelle Loafer, $139.95

Vionic Sellah animal print work shoes

Vionic Sellah, $139.95

What is your favorite comfortable work shoe? 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 and Kyle Dunphy are based in the Washington, D.C. metropolitan area and serve clients across the country. We offer personal styling services, an on-demand e-course, corporate services, and training to become a personal stylist.

Once in a while, you can find Lani Inlander and Real Life Style on Facebook, LinkedIn, Twitter, Pinterest, and Instagram. Mostly, they are happily busy serving their fabulous clients, not hanging out online!

(7) Comments

  1. Suzy Biehl says:

    Thank you so much for the great shoe ideas. I appreciate the prices being listed.

    1. Our pleasure!

  2. 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.

    1. I know! It is so frustrating, isn’t it? They do still have outlet stores though.

  3. Sophia says:

    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.

    1. Which ones do you like?!

  4. Very interesting article!

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