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Shopping Tips

The 2020 Fall Comfort Shoe Guide

The 2020 Fall Comfort Shoe Guide is the fall version of everything you love about the annual Spring Comfort Shoe Guide. And boy, do you guys love that blog! Why have we never before brought you a fall version of the most fashionable shoes from our favorite comfort brands? I have no idea. Please forgive us!

Yes, the 2020 Fall Comfort Shoe Guide is long. However, we have divided it up into the digestible categories of Comfort Brands, Fashion brands, and Waterproof brands. Also, the fall/winter shoe season is long! Aside from a few brands, we have tried to keep things super casual to reflect the way most of us are living these days.

Happy Shopping!

Comfort Brands


Our love of Ally Shoes has been well documented. In fact, I am an official brand ambassador for Ally! They had me at arch support and cushioning. See me on their recent blog post talking about How to Find Your Style. A veteran of some serious foot surgery, these are the only classic high heels and pointed toe flats I can easily wear. Use discount code RLS10 for 10% off your purchase!

Ally Pumps in Gutsy Garnet, $295

Ally Forever Flat in Black Suede/Leather, $195

Ally Bold Block in Tenacious Tan, $295

Ally Mary Jane Pump in Black Suede, $295


I’m sure you’re thinking, “Isn’t this supposed to be a Fall Comfort Shoe Guide?” Oh Birkenstock, how we love thee, even in winter. The original comfort shoe, who knew they would one day be considered trendy? Every time I think my collection is complete, they come out with another design to knock my socks off, like the new shearling styles.

Birkenstock Arizona Big Buckle Shearling, $180

Birkenstock Nagoya Clog, $170

Birkenstock Fanny Big Buckle, $210

Birkenstock Melrose Shearling Boot, $200


Born brand shoes are a client favorite. Their shoes are just soooo comfortable. We have been excited to see Born up the fashion level of their collection over the years. The Born Bhanna Flat is a dead ringer for the Rothy’s loafer, but with a whole lot more support.

Born Bhanna Flat, $84.95

Born Brenta Boot, $134.95

Born Derica Boot, $184.95

Born Syd Boot, $149.95

Born Wynd Boot, $140


Clarks are a perennial fashionable spring and fall comfort favorite for our personal styling clients. Kyle has a stylish pair of short black Clarks boots that I constantly compliment. The answer to a mom wanting a comfortable but stylish shoe to walk the baby around is always the same: Clarks. Our warning is always the same too, don’t stray to the back of the store! The fashionable comfort shoes are in the front.

Clarks Camzin Mix, $109.95

Clarks Kayleigh River Sneaker, $85

Clarks Sharon Heights Boot, $129.95


We love finding super cool Dansko boots in clients’ closets! How Dansko continues to reinvent the same idea, a comfort fall shoe silhouette on their clog base, I don’t know. Dansko boots resemble the more expensive, less comfortable, trendy clog boots from the brand No. 6. I encourage you to look at the many amazing options on Zappos.

Dansko Barbara Boot, $174.95

Dankso Bethanie Boot, $199.95

Dansko Bettie Boot, $189.95

Dansko Bailee Boot, $184.95

Dansko Autumn Boot, $180


Kork-Ease, a brand started in Brooklyn in 1953, was originally known for their fantastically comfortable and fashionable summer sandals and wedges. Their fall comfort shoes are just as fabulous. Kork-Ease carries flat, wedge, and heeled booties. Shop around for your favorite style!

Kork-Ease Ryder Boot, $194.95

Kork-Ease Tincino Boot, $189.95

Kork-Ease Shirome Boot, $189.95

Kork-Ease Kaydin Boot, $214.95


I am a longtime fan of Naturalizer. In my twenties I would stalk their store across the street from Bloomingdales in New York to find comfortable, fashionable shoes post foot surgery. That search used to be quite a challenge. Now the challenge is narrowing down the stylish but supportive choices!

Naturalizer Selah Sneaker, $88.95

Naturalizer Royal Boot, $129.95

Naturalizer Henry Snakeskin Boot, $164.95

Thierry Rabotin

Thierry Rabotin offers designer comfort shoes. That’s a thing! Looking for cool, avant-garde shoes that no one else has? Want to be comfortable? This is the brand for you.

Thierry Rabotin has a flagship store in New York, is carried in specialty stores across the country, and has trunk shows that offer custom combinations of their seasonal styles. There is even an outlet section on the website!

Thierry Rabotin Grayson Flat, $425

Thierry Rabotin Allegra Sneaker, $385

Thierry Rabotin Dakar Boot in Black Suede, $530

Thierry Rabotin Ada Boot in Black Nappa, $570

Thierry Rabotin Mangoro Boots, $600


Vaneli shoes are known for their comfort, style, and wide size range. The supportive shoes come in every size from 4-13 with multiple widths. Hard to fit? There is a Vaneli shoe for you.

What’s new and exciting this year? The selection of waterproof fall comfort options. Want to try them on in person? Head to a Marmi store near you.

Vaneli Talya, $174.95

Vaneli Relis Waterproof Boot, $249.95

Vaneli Quiana Sneaker, $164.95

Vaneli Zeking Waterproof Boot, $224.95


Plantar fasciitis? Heel pain? Back pain? Vionic is the brand for you. Looking for fall comfort shoes? Vionic has oxfords, loafers, sneakers, flat boots, gold faux croc high-heeled boots, and more. They even have a patent combat boot style named Lani! Not my style unfortunately, as you may have guessed. Shop around!

Vionic Serena Ankle Boot, $159.95

Vionic Adela Sneaker, $149.95

Vionic Raina Water Resistant Bootie, $149.95

Vionic Brynn Waterproof Bootie, $199.95

Fashion Brands


Can’t you just imagine how soft the leather is on the AGL Ruffle Top Lace-Up Sneaker? Once a client buys their first pair of AGLs, they are usually addicted. AGL’s combination of comfort, style, and quality is unique.

AGL Ruffle Top Lace-Up Sneaker, $398

AGL Studded Pointy Toe Moc, $390 $195

AGL Notch Bootie, $350

AGL Super Lug Bootie, $495

Cole Haan

Cole Haan has revolutionized the shoe space with their Grand Zero line. Comfortable shoes in unexpected color and material combinations have become Cole Haan’s bread and butter. Hiking boot with a sneaker bottom? Why not? Their low-heeled pumps, mules, and flats are also not to be missed!

Cole Haan Grandpro Rally Court Sneaker, $130

Cole Haan Grand Ambition Slip-On Sneaker, $170

Cole Haan Maci Bootie, $120

Cole Haan Zerogrand Hiker Waterproof, $250

Eileen Fisher

Eileen Fisher’s shoes are just like her clothes, comfortable, stylish, and here to support you. Made in soft, neutral colors, Eileen Fisher shoes typically make a home in your wardrobe and stay for a long time.

Eileen Fisher Prescot Platform Sneaker, $160 $96

Eileen Fisher Amos Knit Wedge Bootie, $265 $149.90

Eileen Fisher Savoy Buckle Bootie, $260


Everlane aims to offer fall comfort shoes with transparent pricing and sourcing. Love their infamous Day Glove flat? Everlane now has the Day Loafer. Looking for something new? Try their reKnit fabric made from recycled plastic bottles.

Everlane Day Loafer, $156 $94

Everlane Modern Utility Chelsea Boot, $178

Everlane Boss Boot in ReKnit, $115

Everlane Modern Utility Lace-Up Boot, $185

Paul Green

Paul Green is a pricy brand, but the quality and comfort is commensurate with the price. These shoes will last for years. I love the brand’s cool, casual vibe.

Paul Green Corinne Sneaker, $349

Paul Green Malibu Boot, $398

Paul Green Nelly Bootie, $375

Paul Green Cimarron Boot, $429

Waterproof Brands


Recognize this first pair? Thankfully Blondo is still selling the Camila Waterproof Bootie. I purchased these last fall as a fashionable, practical, cozy, fall comfort shoe to wear every day. This sums up our love of the Blondo brand! In addition to boots, Blondo now makes sneakers, loafers, and sandals.

Blondo Camila Waterproof Bootie, $169.95

Blondo Saddie Waterproof Bootie, $149.95 $99.90

Blondo Esmee Waterproof, $130

Blondo Flora Waterproof Bootie, $129.95

Ross and Snow

Ross and Snow is an exciting new addition to the 2020 Fall Comfort Shoe Guide. The brand is a fancier, shinier, showier version of Blondo. Their designs are just soooo pretty. I dare you to stop at one pair. Look closely for the camo pattern in the black boot below. Shout out to our client Kim for turning us onto Ross & Snow!

Ross and Snow Emilina Shearling Lined Weatherproof Bootie, $494.95 $248

Ross and Snow Stefana Shearling Lined Weatherproof Bootie, $325

Ross and Snow Renata Weatherproof Camo Boot, $395


Sorel is a super trendy brand of winter weather boots. I have enjoyed watching them get into the fashionable fall comfort shoe game recently.

Sorel Lolla II Cutout, $144.95

Sorel Lennox Moto Boot Cozy, $219.95

Sorel Kinetic Short, $139.95

Sorel Lennox Lace Cozy, $199.95


Just because Timberland is a classic brand, doesn’t mean you have to wear their classic styles. How stylish is this Timberland Courmayeur Valley Chelsea Boot in grey? Check out their “must see” collaboration with Liberty of London! I couldn’t included it here because the sizes are limited.

Timberland Courmayeur Valley Chelsea Boot, $149.95

Timberland Graceyn Waterproof Lace-Up Boot, $169.95

Timberland Jayne Waterproof Bootie, $164.95

Timberland Graceyn Waterproof Motorcycle Bootie, $159.95


Like Timberland and Sorel, Ugg has come a long way in the fall comfort shoe category recently. The Ugg Aureo II Waterproof Boot looks so comfortable and stylish. Super double bonus points that all of these styles are waterproof too!

Ugg Aureo II Waterproof Boot, $139.95

Ugg Aveline Waterproof Boot, $179.95

Ugg Lorna Waterproof Boot, $189.95

Ugg Breeda Waterproof Bootie, $169.95

We hope you have gotten some good shopping ideas from the 2020 Fall Comfort Shoe Guide! Which brand or shoe is your favorite? Let us know in the comments section 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 nationwide. 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!

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