The right shoe can really be the glue that pulls together a stylish outfit. Get the shoe right and the silhouette is perfection. Get the shoe wrong and the whole outfit looks off. Specifically, your flats can’t look too flat, or you will look like you are standing in a hole with your pants puddling around you. Not a pretty vision I know, but so true. Make sure the front of your shoe is as pointy as you can stand, and add some lift in the back, and all will be right.
I always say I am 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 lines up with the silhouette of your pants or skirt. You can look cute and be comfortable, I swear. It just takes a little patience. Hopefully we have done most of the hard work for you, finding the cute comfortable shoes.
Happy Shopping!

Ally Shoes
Ally has been an amazing new resource for our clients. They make a 3-inch heel with arch support unlike anything you’ve ever tried before. Case in point: I haven’t been able to wear heels without pain since my foot surgery in my early 20’s and I can wear these while standing for hours at events. Get your first pair for $50 off with the code LANI50.
Ally Shoes Little Black Heel Suede, $285
Everlane
Everlane makes really modern, designer-looking shoes for a good price. I love my Day Gloves for a casual look, but this new pointed version is a great option for a professional flat.
Everlane The 40-Hour Flat, $115
Ron White
We discovered Ron White at Betsy Fisher, and our clients have become obsessed. They are super comfortable and waterproof, so you don’t have to worry about a sudden change of weather during your commute.
Corso Como
The Corso Como Ryanna pump has amazing cushioning and a walkable block heel for running around your office. They also recently released this woven pair for our Rothys-loving readers who need more support.
Corso Como Julia Knit Flat, $99
Clarks
Clarks has become a go-to for our shopping appointments, as the store in Tysons Corner usually has a good selection. Of course, with all comfort brands, there is the front of the store with the fashionable styles and the back with the more orthopedic-looking styles. Do not wander!
Vaneli
Vaneli is another brand like Clarks, they have a mix of styles for a mix of customers. I don’t know if you remember my awesome chain link sandals c/o Vaneli from last year, but they were so good I bought them in black too and can’t wait to wear them again all summer. They especially have great ankle boots and a terrific size range.
Cole Haan
Cole Haan has long been a staple for both our male and female clients, as they make some of the most comfortable and stylish shoes. This Grand Ambition shoe is more of a walking flat, with a rubber, almost sneaker-like bottom. The skimmer, shown below the Grand Ambition, is your perfect alternative to a pump, as you can still wear this style with dresses and skirts.
Cole Haan Grand Ambition Pointy Toe Flat, $150
Cole Haan Vesta Skimmer Pump, $170
Marc Fisher
The Marc Fisher Zala pump has been one of our favorite shoes for a few years now. We’ve had clients buy the fun seasonal textures, like boucle and snake, as well as the basic black and navy. The Yale boot is a great “flat” boot for both work and casual.
Marc Fisher Yale Chelsea Boot, $143
AGL
AGL has a cult-following for their chic, comfortable shoes. We are not huge fans of the cap-toe ballet flat style for work, but their pumps and loafers are always gorgeous.
Hispanitas
We recently had a mission during a shopping appointment to find comfortable “flats” that our client could wear with skirts and dresses. This ended up being the winner, as there was comfy padding inside and the slight lift did not feel like a painful heel.
Naturalizer
Naturalizer has really stepped up their fashion game recently. They have sleek, minimal styles as well as trendy, fun styles, all with comfort in mind.
Vionic
Vionic is a true comfort brand, specializing in plantar fasciitis and over-pronation. For some clients with severe back or foot issues, Vionic can be a life saver.
This is a post in our series of Work Wardrobe Must-Haves, a companion to our e-book “Your Work-Week Wardrobe with 10 Powerful Pieces.” Subscribe to our email newsletter for more information on how to style these pieces.
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.
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