Get Real Life Style's E-Book Your Work-Week Wardrobe with 10 Powerful Pieces. Subscribe to our newsletter:
Shopping Tips

Fashionable Fall Comfort Shoe Guide 2023

Blog favorite, Fashionable Comfortable Fall Shoes, has landed! 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.

Happy Shopping!

Fashionable Comfortable Fall Shoes - Real Life Style

Lani in some of her favorite fashionable fall Ally Shoes. Photo: Rachel McKean.

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. We had to incorporate the Dr. Martens 3967 Chelsea Boot, a nice twist on the rugged Dr. Martens shoe that never goes out of style. But if you’re looking for something a bit more sophisticated casual, we love the Nisolo Eva Everyday Chelsea Boot and the Marc Fisher LTD Yale Chelsea Boot.

Paul Green Sunny Chelsea Boot -  Real Life Style

Paul Green Sunny Chelsea Boot, $485

Dr. Martens 3967 Chelsea Boot - Real Life Style

Dr. Martens 3967 Chelsea Boot, $170

Nisolo Eva Everyday Chelsea Boot
 Real Life Style

Nisolo Eva Everyday Chelsea Boot, $228

Cole Hahn Westerly Bootie - Real Life Style

Cole Haan Westerly Bootie, $250

Cole Hahn Greenwich Bootie - Real Life Style

Cole Haan Greenwich Bootie, $230

Marc Fisher LTD Yale Chelsea Boot - Real Life Style

Marc Fisher LTD Yale Chelsea Boot, $179

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’re loving the Bordeaux color of the Everlane Lug Chelsea Boot. And of course I had to bring back the Vionic Lani Combat Boot again this year. How could I not?

Eileen Fisher Teddy Tumbled Nubuck Bootie - Real Life Style

Eileen Fisher Teddy Tumbled Nubuck Bootie, $255

LL Bean Camden Hills Chelsea boot -  Real Life Style

LL Bean Camden Hills Chelsea Boot, $169

Vionic Lani Combat Boot -  Real Life Style

Vionic Lani Combat Boot, $170

Jenni Kayne Brooklyn Lug Boot - Real Life Style

Jenni Kayne Brooklyn Lug Boot, $445

Naturalizer Darry Bootie - Real Life Style

Naturalizer Darry Bootie, $170

Everyone The Lug Chelsea Boot - Real Life Style

Everlane The Lug Chelsea Boot, $235

Rothy's The Lug Boot - Real Life Style

Rothy’s The Lug Boot, $269

Block Heel Booties

Thankfully, the block heel is still super trendy this fall! Block heels are the perfect option for a comfortable yet elevated height shoe to dress up your work ensembles or even your casual weekend clothes. The two-tone shoe/heel combination on the Bernardo Nantucket Bootie and the AGL Vetta Precious Bootie make these boots incredibly versatile!

Ally Leather Lower Block Ankle Boot -  Real Life Style

Ally Leather Lower Block Ankle Boot, $475

Blondo Alida Waterproof Bootie - Real Life Style

Blondo Alida Waterproof Bootie, $150

Naturalizer Bay Waterproof Bootie -  Real Life Style

Naturalizer Bay Waterproof Bootie, $140

Franco Sarto Waxton Boot - Real Life Style

Franco Sarto Waxton Boot, $119

Bernardo Nantucket Bootie - Real Life Style

Bernardo Nantucket Bootie, $338

AGL Vetta Precious Bootie - Real Life Style

AGL Vetta Precious Bootie, $455

Western-Inspired

This is Kyle’s current favorite fashionable fall comfort shoes trend. The trend 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. The Paul Green Shilo Western Bootie combines both the western trend and the slouchy boot trend making a comeback this year!

Vince Camuto Salintino Wester Boot -  Real Life Style

Vince Camuto Salintino Western Boot, $139

Rag & Bone Western Block Heel Bootie - Real Life Style

Rag & Bone Western Block Heel Bootie, $495

Vionic Regan Ankle Bootie - Real Life Style

Vionic Regan Ankle Bootie, $180

Paul Green Shilo Western Bootie - Real Life Style

Paul Green Shilo Western Bootie, $520

Thursday Indio Boots - Real Life Style

Thursday Indio Boots, $180

Moto Boots

The fashion trends are moving faster than ever! The Moto boots that were popular not that many years ago are back. Below we have options for every Moto boot height you could want! If you’re into a lower ankle boot, try the Vionic Rhiannon Ankle Boot. Try the Vance Boot if you want a taller Moto boot.

Vionic Rhiannon Ankle Boot -  Real Life Style

Vionic Rhiannon Ankle Boot, $190

Vince Camuto Verglia Bootie - Real Life Style

Vince Camuto Verglia Bootie, $159

Sarto By Franco Sarto Vance Boot - Real Life Style

Sarto by Franco Sarto Vance Boot, $220

Gentle Soul Signature Slit Faux Shearling Moto Bootie - Real Life Style

Gentle Soul Signature Slit Faux Shearling Moto Bootie, $170

Donald Pliner Harness Bootie - Real Life Style

Donald Pliner Harness Bootie, $298

Shoeties

Looking for something between a shoe and a bootie? Look no further. This year we’re dedicating an entire section in our fashionable fall comfort shoes edition to the “Shoetie.” We love the shoetie for an option that’s lower on the ankle when, in the early fall, you’re not quite ready to commit to a full boot option. This year the Nisolo Mia Everyday Ankle Bootie comes in a variety of great neutral options, and they’ve even added suede to the line.

Eileen Fisher Melrose Bootie - Real Life Style

Eileen Fisher Melrose Bootie, $275

Dr. Scholl's Ruler Shootie - Real Life Style

Dr. Scholl’s Ruler Shootie, $50

Toms Slip On Wedge Shooties -  Real Life Style

Toms Slip On Wedge Shooties, $100

Nisolo Mia Everyday Ankle Bootie - Real Life Style

Nisolo Mia Everyday Ankle Bootie, $228

Blondo Sandra Waterproof Bootie - Real Life Style

Blondo Sandra Waterproof Bootie, $130

Waterproof and All-Weather Boots

Who doesn’t love a shoe that both protects from the elements and completes a look? The Sorel Joan Now Chelsea Boot combines rugged and trendy for the perfect weatherproof boot in a variety of color options. And although I debated whether or not to add a regular rain boot in this year, how great is the sage color of the Everlane Rain Boot?

Sorel Emelie III Chelsea Boot - Real Life Style

Sorel Emelie III Chelsea Boot, $160

Sorel Women's Joan Now Chelsea Boot - Real Life Style

Sorel Women’s Joan Now Chelsea Boot, $190

Blondo Danika Waterproof Bootie - Real Life Style

Blondo Danika Waterproof Bootie, $160

Cole Haan Greenwich Waterproof Ankle Booties - Real Life Style

Cole Haan Greenwich Waterproof Ankle Booties, $225

Everlane The Rain Boot - Real Life Style

Everlane The Rain Boot, $85

Knee-High Boots

Knee-high boots are a great styling tool for winterizing a dress or skirt. Pair your sweater dress with a tall boot and you have an instant fall ensemble. We love the new charcoal color of the ever perfect Stuart Weitzman 5050 Suede Over-the-Knee Boots. And for those of you who might need a wide calf option, try the Vionic Phillipa Tall Boot, available in regular and wide calf, or the Naturalizer 27 Edit Edda Wide Calf Boot.

Bernardo Hammond Over the Knee Boot - Real Life Style

Bernardo Hammond Over the Knee Boot, $358

Blondo Starling Waterproof Knee High Boots - Real Life Style

Blondo Starling Waterproof Knee High Boots, $220

Vince Ramona Square Toe Mid Heel Riding Boot - Real Life Style

Vince Ramona Square Toe Mid Heel Riding Boot, $595

Naturalizer 27 Edit Edda Wide Calf Tall Boot - Real Life Style

Naturalizer 27 Edit Edda Wide Calf Tall Boot, $265

Stuart Weitzman 5050 Suede Over-the-Knee Boots - Real Life Style

Stuart Weitzman 5050 Suede Over-the-Knee Boots, $795

Vionic Phillipa Tall Boot - Real Life Style

Vionic Phillipa Tall Boot, $250

Clogs

Clogs are always a favorite among our clients. Giving platform height without sacrificing comfort, they’re a great all day shoe. The Eileen Fisher Suede Clog really caught our eye this season for its neutral elegance. And the Beklina Ribbed Clog comes in so many colors, we struggled to decide which one to put in the blog!

Beklina Ribbed Clogs - Real Life Style

Beklina Ribbed Clogs, $290

Everyone The Puffa Flatform - Real Life Style

Everlane The Puffa Flatform, $155

Dansko Talulah Clog - Real Life Style

Dansko Talulah Clog, $145

Nisolo All Day Heeled Clog - Real Life Style

Nisolo All Day Heeled Clog, $180

Eileen Fisher Suede Clog - Real Life Style

Eileen Fisher Suede Clog, $250

Mules

We also had to add a new section for Mules in the annual fashionable fall comfort shoes post this year. Wildly popular, comfortable and easy to throw on, Mules will definitely be a staple shoe for us this season. Lani has been wearing the pairs she bought in Morocco non-stop. The embellished Kurt Geiger Olive Mule (available in natural and black) is selling quick! But if you’d prefer something less flashy, Birdies recently released some new colors and limited edition styles in The Dove mule. Be sure to check out all the options.

Birdies The Dove - Real Life Style

Birdies The Dove, $130

Dansko Lexie Leather Mule - Real Life Style

Dansko Lexie Leather Mule, $130

Nisolo All-Day Heeled Mule - Real Life Style

Nisolo All-Day Heeled Mule, $162

Nisolo Ama Woven Mule - Real Life Style

Nisolo Ama Woven Mule, $180

Kurt Geiger Olive Embellished Mules - Real Life Style

Kurt Geiger Olive Embellished Mules, $150

Jenni Kayne Suede Mule - Real Life Style

Jenni Kayne Suede Mule, $395

Loafers

The chunky loafer is back this season! If you’re looking for a trendy chunky loafer, this croc patent leather Donald Pliner Loafer fits the bill perfectly. Don’t worry, for those of us who aren’t into a chunky loafer, we’ve got options for you too! The Tory Burch Jessa Bit Loafer Pump and the Nisolo Everyday Slip On Loafer are more classic and a little less chunky.

Tory Burch Jessa Bit Loafer Pump - Real Life Style

Tory Burch Jessa Bit Loafer Pump, $378

Donald Pliner Hope Slip On Loafer Flats - Real Life Style

Donald Pliner Hope Slip On Loafer Flats, $188

Nisolo Everyday Slip On Loafer - Real Life Style

Nisolo Everyday Slip On Loafer, $200

Vionic Kinsley Loafer - Real Life Style

Vionic Kinsley Loafer, $130

Vince Camuto Becarda Pointed Toe Loafer - Real Life Style

Vince Camuto Becarda Pointed Toe Loafer, $111

Rothy's The Lug Loafer - Real Life Style

Rothy’s The Lug Loafer, $229

Naturalizer Darry Leather Loafer - Real Life Style

Naturalizer Darry Leather Loafer, $120

Flats

Speaking of trends, the classic Mary Jane is also having a moment this season. We’ve included two options here that are topping our list of favorites, the Sam Edelman Michaela Mary Jane Flat and the Franco Sarto Tinsley Mary Jane Flat. And Ally, our absolute favorite comfort heel brand, recently released a cap toe line including the Ally Cap Toe Flat. A perfect fall flat to pair with your work ensemble!

Birdies The Goldfinch - Real Life Style

Birdies The Goldfinch, $150

Sam Edelman Michaela Mary Jane Flat - Real Life Style

Sam Edelman Michaela Mary Jane Flat, $130

Everlane The Day Ballet Flat - Real Life Style

Everlane The Day Ballet Flat, $145

Ally Cap Toe Flat - Real Life Style

Ally Cap Toe Flat, $245

Cole Haan Vanessa Skimmer - Real Life Style

Cole Haan Vanessa Skimmer, $170

Dansko Lace - Real Life Style

Dansko Lace, $130

Franco Sarto Tinsley Mary Jane Flat -Real Life Style

Franco Sarto Tinsley Mary Jane Flat, $115

Pumps

Rounding out our fashionable fall comfort shoes this season, are the ever essential pump! If you haven’t heard, red is the color of the season this fall. Luckily the Marc Fisher Zala Block Heel Pump came through for us in the red pump category. We love it! And if you thought the Ally flat wasn’t quite the right style, you’re in luck. They also came out with the Ally Leopard Cap Toe Pump, the perfect eye catching, fierce pump!

Ally Leopard Cap Toe Pump - Real Life Style

Ally Leopard Cap Toe Pump, $345

Ally Black Suede Lower Black Heel - Real Life Style

Ally Black Suede Lower Block Heel, $325

Nisolo Fiorela Go-To Mid Heel - Real Life Style

Nisolo Fiorela Go-To Mid Heel, $180

Paul Green Rendi Pointed Toe Pump -  Real Life Style

Paul Green Rendi Pointed Toe Pump, $379

Sarto by Franco Sarto Devin Slingback Pump - Real Life Style

Sarto by Franco Sarto Devin Slingback Pump, $140

Naturalizer Warner Pump - Real Life Style

Naturalizer Warner Pump, $99

Sam Edelman Tarra Slingback Pump Real Life Style

Sam Edelman Tarra Slingback Pump, $140

Marc Fisher Zala Block Heel Pump - Real Life Style

Marc Fisher Zala Block Heel Pump, $160

Fashionable Comfortable Fall Shoes

That’s a lot of comfortable fall shoes to pick from! What can we say? We simply couldn’t choose! 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 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!

(13) 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!

        1. I can’t wait. Same issue as the two people above!

  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!

Leave a Reply

Your email address will not be published. Required fields are marked *