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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. 

The correct shoe can be the glue that holds a stylish outfit together. Get the shoe correct and the silhouette is just right. Get the shoe wrong and the whole outfit looks off. If your flats are too flat, you’ll look like you are standing in a hole with your pants puddling around you. Not a pretty vision, but something Kyle and I 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!


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 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, $399

Ally Shoes

Ally has been an amazing new resource for our clients. They make a flat, and both a classic and block-heeled pump in 2- and 3-inch heights. This is arch support and padding unlike anything you’ve ever experienced in a heel. Case in point: I haven’t been able to wear heels without pain since foot surgery in my early 20’s. But I can wear my classic pump in Gutsy Garnet while standing for hours at events. My latest toy? Ally’s black patent kitten heel pump! Get 10% off your first order with the code RLS10.

Comfortable and Fashionable dress shoes for work for Real Life Style, Ally black suede heels

Ally Shoes Black Suede Classic Pump, $325

Comfortable and Fashionable dress shoes for work for Real Life Style, Ally caramel leather pointed flats

Ally Shoes Courageous Caramel Leather Flat, $225– Lani owns these too!

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

Ally Shoes Fierce Leopard Block Heel Pump, $325


Kyle and I have been so enthusiastic about Birdies shoes the last few seasons 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 nailed it. My black faux shearling Lark slides are currently in high rotation! They are still available in pink faux shearling and suede, which I am trying to resist….

Birdies Heron Loafers, $130


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.

Clarks Laina Flats, $120

Cole Haan

Cole Haan has long been a staple for our male and female clients who are looking for fashionable and comfortable work shoes. We are excited to say that their offerings have gotten even fashionable (and comfortable!) this past year. You should peruse the site if you haven’t in a while. Unfortunately, this is another brand that has closed their local stores.

Cole Haan Grand Ambition Pumps, $180

Cole Haan Viola Skimmer Flat, $150


Believe it or not, clogs are not the only comfortable work shoe that Dansko makes. We also like the Dansko Kira flat for a more casual workplace. And how fabulous is the bright blue of the Dansko Lisanne Flat?

Dansko Larisa Flat, $124.95


Dansko Lisanne Flat, $79.20 – $188.44


Everlane makes really modern, designer-looking shoes for a decent price. I love my Day Gloves for a more casual look with a slim pant or skirt. Most people start with a pair in black, then accumulate many more of the 10 colors offered!

Comfortable and Fashionable dress shoes for work for Real Life Style, Everlane Day Gloves

Everlane Italian Leather Day Glove, $105

Marc Fisher

The Marc Fisher Zala pump has been one of our clients’ favorite shoes for a few years. We’ve had clients buy fun seasonal textures like boucle and snake, as well as the basics—black and navy leather. The Zala pump also comes in varying shades of beige to match diverse skin tones.

Marc Fisher Zala Pump, $160

Ron White

We discovered Ron White at the Betsy Fisher boutique. Our clients fell in love. The Dory pump is one of my favorite black heels for its comfort and style. They are also waterproof, so you don’t have to worry about a sudden change of weather during your commute. Yes, the shoes are pricey, but you can usually find a large selection of Ron White at Nordstrom Rack!

Ron White Kadesha Loafer, $445


Naturalizer has really stepped up their fashion game in recent years. So much so that I should apologize now if we’ve already sold out all of the stylish shoes below by the time you try to click through to buy them! We are particularly excited this season about the new more colorful, more fashion forward Naturalizer sub-brand, 27 Edit.

Naturalizer Florence Pump, $135

Naturalizer Avrie Slingback Flat, $120


Vaneli is a brand similar to Clarks. They have a mix of styles for a mix of customers. I own a pair of awesome chain link dressy slide sandals c/o Vaneli that are so good I then bought them in another color. And now this season they made them with a super comfy, cushioned bottom. How many pairs of “the same” chain link sandal can I have? No, seriously. How many?

Vaneli Maylea Pumps, $165

Vaneli Ganet Pointy Toe Flat, $144.95


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. How fashion forward is the heel on the Vionic Luxana Flat? We love it!

Vionic Luxana Flats, $139.95

Vionic Kensley Loafer, $129.95

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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