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Shopping Tips

Fashionable Fall Comfort Shoes 2022

We are back, with no less than blog favorite, Fall Comfort Shoes! One of the most loved blogs of the year, our annual fall comfort shoe extravaganza combines our seasonal client shopping experience with the trends. What proof do we have that fashion and comfort can coexist?

Real Life Style stylists don’t let their clients wear uncomfortable shoes! And we don’t wear them either. At least not while shopping till we drop! Nor are we willing to sacrifice looking fashionable. Please let us know which shoes or boots are your favorites in the comments below. No pressure to choose the Lani Combat Boots from Vionic!

Happy Shopping!

Chelsea Boots

You can never go wrong with a Chelsea boot. The look has become a classic, and works with our favorite new denim styles. If you want something really flat, this silhouette is probably your best bet. However, there are also fashionable, comfortable Chelsea boot options with stacked heels and wedges.

Eileen Fisher Roy Chelsea Boot, $265

Vionic Shantelle Waterproof Leather Bootie, $169.95

Eileen Fisher Lilou Nubuck + Recycled Stretch Knit Bootie, $275

Munro Jackson Bootie, $230

Born Cove Waterproof Chelsea Boot, $159.95

Rothy’s Utility Boot, $259

Lug-Sole Boots

If you love the Chelsea boot but want a more modern version, try the lug-sole boot! This style can now be found in flats, platforms, lace-ups, and everything in between! We and our clients’ are big fans of the Vionic Lani boot, not just for the name and multiple color choices, but for its comfort and versatility. It also comes in wide on the Vionic site.

Naturalizer Verney Waterproof Bootie, $160

Vionic Lani Combat Boots, $169.95

Vionic Karsen Boots, $179.95– These are actually Lani’s fave!

Thursday Reign Boot, $168

Pedro Garcia Zona Chelsea Boot, $695

Wonders Waterproof Lug Sole Bootie, $269.95

Andre Assous Monda Weather Resistant Chelsea Boot, $259

Square Toe Shoes

Along with the Seventies/Nineties trend, square toe boots and shoes are back. This can be subtle, like the La Canadienne waterproof booties for work. Or it can be exaggerated and fashion-forward, like one of our favorite flats, the Naturalizer 27 Edit Avrie Flat. Are you surprised to find out that Kyle owns it in a fabulous magenta suede?

Naturalizer 27 Edit Avrie Flat, $119.95

Franco Sarto Waxtona Boot, $170 $152.99

La Canadienne Tahlia Boot, $550

Calvin Klein Alanta Square Toe Pump, $109

Donald Pliner Kath Boot, $298

Paul Green Olivia Boot, $465

Blondo Salome Waterproof Bootie, $149.95– A Client favorite for a second season!

Naturalizer Axel Waterproof Knee High Boot, $250– $100 off at Zappos right now!


This is Kyle’s current favorite trend, as it feels updated and fun. Pair a western-style boot with jeans and a sweater for an instant outfit. If you already have a pair of comfortable cowboy boots, now is the time to break them out. If you’re looking to dip your toe in the trends, the Franco Sarto Forta Boot below has a great mix of all the boot trends while still being simple and classic!

Franco Sarto Forta Boot, $150

Kenneth Cole Kara Western Boot, $168.95

Naturalizer Gaby Zip Western Boot, $160 $138.75

Pikolinos Llanes Boot, $209.95– A new favorite brand of RLS clients!

Sofft Aisley Bootie, $159.95

Thursday Indio Boots, $180

Paul Green Niche Pointed Toe Bootie, $439


Platform boots are having a moment, but keep in mind that this is a very “seventies” iteration of platforms. There will be clog-styled boots, stacked heels, and wooden soles. I love this trend but am too worried I will break an ankle…

Andre Assous Sanaa Water Resistant Platform Chelsea Boot, $259

Bernardo Shawnee Boot, $338

Dr. Scholl’s Wild About Boot, $150

Fitflop Pilar Platform Bootie, $180

Blondo Raquel Waterproof Boot, $159

Wonders Lightweight Fashion Suede Boot, $219.95

Waterproof and All-Weather Boots

If you look throughout the blog, you’ll see other great waterproof styles (like the Vionic Shantelle Waterproof Bootie or the Blondo Raquel Waterproof Boot), but here are the boots we would wear to take the kids to school or walk the dog while it’s downpouring. These are guaranteed to be practical and fashionable.

Sorel Hi-Line Heel Chelsea, $189.95

Ugg Harrison Waterproof Bootie, $140

Naturalizer Tex Boot, $190

Sofft Sharnell Low Boot, $129.99

Geox Iridea Amphibiox Waterproof Lace-Up Boot, $230

La Canadienne Brendan Waterproof Combat Boot, $550

Knee-High Boots

Knee-high boots are still a great styling tool for winterizing a dress or skirt. If you have a hard time finding calf sizes that are narrow or wide enough, Duo Boots has seven different calf sizes for all of their boots. Certain styles also come with different calf heights! This brand is a game changer!!!

Blondo Sierra Waterproof Over the Knee Boots, $239.95– Lani and Kyle own multiple versions of these!

Duo Boots Verity Knee High Boots, $236

Gentle Souls Best Knee High Boot, $288.95

Naturalizer Brent Waterproof Knee High Boot, $230

Kork-Ease Sydney Boot, $260– A client favorite this season!

Vaneli Caissy Boot, $225


The unexpected sold-out shoe this season is the Birkenstock Boston. Kyle has been touting these as the best pandemic purchase since 2020. She first dipped her toes in the water with an olive suede shearling pair from Poshmark. She loved them so much she then paid full-price for the pink shearling Birkenstock Boston Clogs last year. (Both of these colorways are not current for this season. You may look on Poshmark for them, but currently all of the Birkenstock clogs are going for above retail price!)

Birkenstock Boston Shearling, $170

Dansko Brenda Clog, $139.95

Born Hilary Clog, $94.95

Dansko Caia Nubuck Clog, $139.95

Andre Assous Skylar Stud Slingback Clog, $239

Born Shaya Clog, $120 $66

Dansko Professional Clog, $144.95

Sofft Ameera Mule, $129.95

Chunky Loafers

What is a chunky loafer? Well, it could be any combination of all the aforementioned boot trends. Loafers with lug-soles, platforms, square-toes, and block heels are all trending right now. This typically preppy silhouette is now being styled with some edge.

AGL Sirena Penny Loafer, $510

Blondo Dulce Waterproof Loafer Pump, $119.95

Vince Camuto Becarda Pointed Toe Loafer, $110.95– A fall favorite!

Vionic Sellah Square Toe Loafer, $139.95

Cole Haan Newburg Lug Loafer, $160

Vince Camuto Darmitta Loafer, $119

Naturalizer Darry Leather Loafer, $120


The fashion cycles moved so quickly in 2022 that flats are now trending again. Not just flat shoes, which obviously haven’t gone anywhere. Specifically, the ballet flat is slated for a return to fashion for fall. Of course, they’re a little different than the ubiquitous 2010 shoe that we all considered the default. The toe box is longer and either pointed or squared off, and we’re seeing lots of adorable Mary Janes. Check out the linked Vogue article for fashion inspiration!

Birdies Goldfinch Flat, $110

Thierry Rabotin Cathie Black Suede Flat, $395

Trotters Honesty Flat, $109.95

Birdies Heron Flat, $130

Italeau Mara Waterproof Flat, $239

Camper Right Nina Leather Ballet Flat, $160

Everlane Italian Leather Day Ballet Flat, $130

Vionic Dahlia Flat, $109.95


White tennis shoes and retro running shoes are two sneaker styles that have outlasted all other trends. The Hartjes Phil Lace/Zip Leather is a favorite for our clients who have a tough time finding comfortable shoes. Check out Comfort One stores to find your size!

Hartjes Phil Lace/Zip Leather, $258.95

Munro Piper Sneaker, $200

Birdies Roadrunner Sneaker, $140 $98

Cole Haan GrandPro Topspin Sneaker, $140

On Cloud 5 Combo, $149.99

Rag & Bone Retro Runner Sneaker, $245

Vaneli Yavin Sneaker, $175


Our favorite comfortable dress shoe brand, Ally Shoes, just released styles in embossed scarlet, sand, and cognac. And stay tuned for more exciting winter styles launching from them soon! If you’re looking for a super low-heel with high-style, the Sarto by Franco Sarto Diva Pointed Toe Pump is a standout. We even sold it to a client in the fuchsia below!

Ally Shoes Cognac Embossed Leather Lower Block Heel, $335

Marc Fisher LTD Zala Block Pump, $159.95

27 Edit Naturalizer Faelyn Leather Pump, $135 $87.75

Sarto by Franco Sarto Diva Pointed Toe Pump, $140

Sarto by Franco Sarto Rita Pointed Toe Pump, $129.95– How cool is this shoe?!

That’s a lot of shoes to choose from! What can I say? We were making up for lost time! Let us know which shoes or boots are your favorites 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!

(12) Comments

  1. Kara Corridan says:

    I’ve been patiently waiting your next blog! Any chance you’ve got a gift guide in the works? I need to give my family Christmas ideas!

    1. Thank you for your patience! As always, so many ideas, so little time ;). Hoping to get one out soon. (I can hear my team cringing as I write this…) Any specific category requests?

      1. Gifts for men!! I have loved your pass by and guide for your husband

  2. Megan K says:

    I’m feeling on your wave length as I honestly bought Born low profile heel boots yesterday!!

    1. Love Born! Awesome!

  3. You always give the best recs at the perfect time! I have been looking for a non-black boot and I ordered the Thursday Indio Boots the second I opened the email!

    1. Awesome! We love Thursday boots.

  4. Excited to see this post! Am I the only one that needs a refresher on how to pair outfits + shoe? Booties in particular intimidate me because Im certain I’ll wear them wrong 🙂

    1. Same! Especially with the change in pant styles.

      1. We have been getting a lot of that question lately. If I don’t post an answer here, I’ll put something clever and succinct in the next newsletter!

  5. Lani, this list was more than I expected when I started reading it. Researching EVERY type of shoe is very helpful to your readers. However I already bought my comfortable boots earlier in the season this year. I had to replace my worn out black knee high “leather” boots that I held onto for years because they were so comfy, but was reluctant to do so. I found the Naturalizer Rena Boot with a flat heel and in nice black leather at Nordstroms, which not only has 3 calf width sizes but also comes in Wide width, and only $200. So comfortable and I have a bunion on my left foot! For ankle boots I liked the Easy Spirit Women’s Tamara Heeled Square Toe Booties for $149 from Macy’s.

    1. Donna, I’m sorry we were too late to help you. However, your work will help other readers! I’m going to add your suggestions to this blog :). Thank you!

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