2023 Fall Boots: 27 Cool Beauties to Boot Up Your Autumn

Our annual Fall boots article, showcasing 27 trending looks for business, casual and dressy…how fun!

When the temperatures start to drop, no look is complete without a great pair of boots (as if we had to tell you that). But in addition to the comfort, there comes the fashion. And this season, from cowboy to combat, there are plenty of options out there to keep your feet warm and cozy all season long.

So let’s get into the trends.


A cornerstone of vintage Americana, boosted by the fashion tsunami of the Y2k trend, cowboy boots will continue to dominate as a staple in our 23/24 wardrobes. From full-on Swiftie fringing, to classic Western, to bring-the-bling, there are no wrong answers here.

Like this sparkling beauty from Windsor. Surprisingly versatile, they will look as stunning with your knit mini as they will paired with a denim maxi.

Windsor, Made To Sparkle Rhinestone Cowboy Boots $64.90

An absolute classic of a boot, you’ll have a difficult time finding an outfit that won’t go with these dark chocolate suedes.

P.A.R.O.S.H., Decorative Stitch Cowboy Boots $326

A fringe this good deserves those jeans to be tucked in

Cato, Extreme Fringe Western Boots $59.99


Comfort with a touch of edge, the combat boot remains a popular choice as we stomp headlong into the oncoming months of slippery sidewalks.

All the commanding presence of the classic lace-up, with the convenience of a quick zip.

Free People, Emmett Lace-up Leather Boot $129.99

(on Sale NOW from $268)

A chunky cute combat boot with a vegan soul (and sole too)…

Matisse, Miss Me Combat Boot $35

(on Sale NOW from $100)

Of course, we’d be remiss if we neglected to include the one and only, Dr. Martens. Here’s the coveted boot re-envisioned in a fresh silhouette.

Dr. Martens, Lace Up Combat Boot $291


They were polarizing when they first came out, but like all things fashion, this fall seems to be the beginning of the new cycle for the divisive sock boot.

Leave it to Burberry to take their iconic pattern and use it in their new version of the sock boot…

Burberry, Check Knit & Leather Sock Boot $789.99

(on Sale NOW from $990)

This creamy white, knee-high version from Circus NY reminds us of our favorite cozy pair of corduroys…

Circus NY, Simone Knee High Boot $44.99

(on Sale NOW from $140)

This cool, gray customer is the universal neutral your fall wardrobe is craving…

Coconuts, Hudson Sock Boot $38.50

(on Sale NOW from $110)


It’s not like they were ever out of style, but with the transition from summer to fall comes the return of the beloved ankle boot. While the colors and styling reflect this season, the silhouette remains eternal.

Case in point – the ankle boot visits cowboy country this season…

Ba&Sh, Curt Ankle Length Cowboy Boot $450

The archtypal, sleek black bootie, freshened up in this season’s trending pointed toe.

Windsor, Back To Basics Faux Leather Ankle Booties $34.90

Of course there is NO way we’re leaving our Barbie love out of the picture for fall.

Circus NY, Rosalie Sculpted Heel Boot $47.99

(on Sale NOW from $120)


The humble rain boot has been making quite the splash (oh the puns begin again) these past seasons. As we head into fall however, we’re seeing the new versions that are now nearly indistinguishable from your other modern boot silhouettes.

Case in point, this waterproof, off-white version from Aquatalia

Aquatalia, Scilla Weatherproof Boot $249.99

Not only is this boot waterproof, it’s also eco-friendly with recycled PET plastic to create the upper and repurposed foam and polyester in the lining.

Palladium Boots, Pampa Travel Lite + WP $150

These western style rain boots may very well have you literally singing in the rain…

Matisse, Annie Rain Boot $60


The jury is still out on whether over-the-knee, but for certain knee-high boots will continue to add that element of drama to your awesome autumn outfits.

A little slouch will go oh-so well with a posh midi…

Journee Collection, Aneil Stacked Heel Knee High Boots $65.99

(on Sale NOW from $109.99)

These roomy fit, flat heel boots from Via Roma 15’s new season will look amazing with a fitted sweater dress.

Via Roma 15, V-Plaque Leather Boots $396

These croc-embossed beauties are a great way to rotate in this fall’s hot red color.

Schutz, Croc-Embossed Knee High Boot $315


It’s true, our obsession with the chunk continues, more so when we’re talking about chelseas. There’s just something so edgy about them.

Parisian brand The Kooples gives us chunky with a little heel.

The Kooples, Black Leather Heeled Boot $213

(on Sale NOW from $355)

This deep green will go so well with your moody autumnal colors.

Coconuts, Indie Chelsea Boot $35

(on Sale NOW from $100)

These contemporary stunners from Proenza Schouler’s new season are meant to be SEEN

Proenza Schouler, Storm Chelsea Boots $950


Just when you thought it was safe to put away your serpents, yes, the reptile print trend is back.

You could say this is one colorful constrictor, ready to add some big luxe to your wardrobe neutrals.

Cato, Faux Leather Snakeskin Tall Boots $54.99

On a more monochromatic note, this gorgeous green print is sumptuous all on its own.

Matisse, Annabelle Boot $129

Finally these handsome crocs complete with kitten heels.

Joie, Kehlani Croc-Embossed Leather Boots $149

(on Sale NOW from $398)


Despite what some might consider a misnomer, white boots for autumn have been popular for several seasons now. This year, we’re giving our love towards cool ivory, light toffee, and off-white shades.

This cool, ivory customer will absolutely complement all your autumnal shades.

Circus NY, Emmy Tall Boot $140

Looking for somethings slightly more rugged to amp up your street wear looks? These creamy colored army boots will do so in masterful style.

Palladium Boots, Pampa HI $85

Finally, these off-white wonders from JW Anderson’s new season have so much visual interest, you may have a hard time not staring at your feet.

JW Anderson, Padlock Ankle Boots $995

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