Kick It Up a Notch: Modern Cowgirl Boots for Elevating Any Fall Outfit

Our editors independently select these products. Making a purchase through our links may earn PLEIN AIR a commission.

Unless you’ve been living under a rock, you’re likely well aware of Western ware’s rise to fashion fame over the past few years. Everywhere we turn, there are articles, TikTok  videos, and Pinterest boards all dedicated to the growing popularity of the coastal cowgirl aesthetic. For those of us who grew up on Shania Twain and spent more Halloweens under a cowgirl hat than we care to admit (just me?), this lengthy trend is a warm return to our idyllic dress-up days of girlhood, perhaps because so many feel welcome adopting it.

There are, of course, many elements that go into a coastal cowgirl outfit, but my personal favorite and arguably the most iconic standout is the cowgirl boot. Cowgirl boots are ultra versatile and don’t require the same amount of confidence that a cowgirl hat does. (If you’ve ever bought a statement hat only to let it collect dust in your closet, you know what I’m talking about.)

I’ll pretty much find any excuse to break out my pointed-toe cowgirl boots (literally packing them for a funeral as we speak), but fall is by far the best season for sporting the style for the following reasons.

Unless you’re buying a true pair of women’s work boots, your boot is most likely better suited for eating out than romping around in the mud or snow (because  winter and mud season is a separate case study.) Also, if you’ve ever worn cowgirl boots before, you likely know those suckers can get hot and uncomfortable in warm weather (sorry summer.) Therefore, the best time to wear your cowboy boots is when it isn’t too hot and there isn’t any snow or cruddy weather on the horizon, a.k.a.  autumn. Ankle season instead of shoulder season, perhaps? 

So, without further ado, here are our 7 favorite cowgirl boots and cowgirl boot outfit ideas for this fall 2023.

Our 7 Favorite Women’s Cowgirl Boots for Fall Outfits 2023:

• Lucchese — Nicole,  $595
• Steve Madden — Abilene Black Leather, $249
• Jeffrey Campbell — Amarillo, $270
• Ganni — Embroidded Western Boot, $725
• AllSaints — Kacey Western Boot, $419
• Reformation — Olive Western Boot, $498
• Khaite — Dallas Western Suede Knee Boots, $1,380

Lucchese, Nicole,  $595

Styled with: Line by k dress, Quay sunglasses , Mat and Nat crescent bag, Madewell trench coat (The jacket’s currently sold out, but you can shop a similar one here.)

When it comes to authenticity, Lucchese is about as real as it gets. Handmade in Texas with cowhide leather, these boots are for the most elegant of cowgirls. If you don’t believe us, check out how cute they look on one of our style icons, Ty Haney. A classic pair of black cowgirl boots can go with pretty much anything, but since these lean more classy than classic, we’re dressing them up with a high-neck, low back dress and modern trench coat. 

Steve Madden, Abilene Black Leather, $249

Styled with: Mango skirt, Madewell top, Axel Arigato sweater, Madewell sunglasses like these , Mat and Nat crescent bag

The first ever pair of cowgirl boots I bought as an adult were a pair of used Steve Madden boots from a thrift store in LA. With many miles behind them, these boots still look great and are easily the most complimented piece in my wardrobe. For anyone looking to buy their first pair of cowgirl boots, but don’t want to pay over $500 for an “authentic” pair, I’d recommend this simple but stunning pair from Steve Madden.  The sleek square toe and tall shaft give these boots a polished (read: expensive) look. I’d pair them with an all denim look for a nod to Shania in the 90s.

Jeffrey Campbell, Amarillo, $270

Styled with: Hikerkind shorts, Clare V trucker hat, Aritzia sweatshirt, Madewell sunglasses, The Frankie Shop trench coat

For a little bit of spice (at a reasonable price), we’re loving these under $300, metallic, red hot boots by Jeffrey Campbell.  No matter where you go, fall weather is undeniably unpredictable. One minute we’re bundling up for a crisp breeze, the next we’re undressing from the scorching sun.  With fickleness in mind, we’ve styled these boots alongside neutral colored layers to keep both your outfit and your temperature balanced at all times. 

Ganni, Embroidered Western Boot, $725

Styled with: Halfdays top, Halfdays legging, Madewell trench coat like this , L.L. Bean boat and tote, Madewell sunglasses like these .

Oh, Ganni, we’d follow you anywhere…even if anywhere leads to spending part of next month’s rent on a pair of boots. Born in Copenhagen, Denmark, this Danish brand might not be the first place you’ll look for a new pair of (pardon our French) shit-kickers, but you’ll certainly be glad you did. Our only gripe with these boots is that the shaft tends to run on the narrower side. If you’re looking for a cowboy boot with extra give around the calf (say for those like me who need a wide calf cowgirl boot), these won’t be the most comfortable option for you. If this isn’t a concern, these would look oh-so-cute styled with the new Spritz set from Halfdays and a modern, plaid trench coat.

AllSaints, Kacey Western Boot, $419

Styled with: Stetson hat, reformation denim shorts, madewell sunglasses, boat and tote, mariposa stables sweater

Appropriately named after our northstar of modern cowgirl style, these cosmic kickers bring a new shiny attitude to the world of Western ware. Since these boots are bound to steal the show, we recommend styling them with a pair of casual jean shorts and sweater. And of course, since you’re a real cowgirl (at least while wearing them), you’ll need a Stetson hat to top it off (literally). 

Khaite, Dallas Western Suede Knee Boots, , $1,380

Styled with: Mango top, Mango jeans, madewell sunglasses, Stetson hat

If the devil is in the details, then welcome to Hell, honey. This posh Western boot by Khaite is made in Italy with embroidered pull straps and three-row tonal stitching. As their website says, these boots were made for the urban cowgirl, and with a price point above $1,000, we believe them. While you certainly won’t be wearing them to your local rodeo, these boots would look great on the streets of Aspen (girls trip anyone?). We’ve tastefully paired them with an approachable denim set (pants and jacket) from Mango for the perfect high-low look.

Reformation, Olive Western Boot, $498

Styled with: Tio Lee Bottoms, Tio Lee Top, Halfdays Davis Jacket, Halfdays Bucket Hat, Quay sunglasses 

I’ll be the first to admit that this list is more focused on fashion than it is true cowgirl function. But I’m also willing to bet the majority of us only need outfit ideas for apple picking and farmers’ markets this fall, and not for daily life on the ranch. Because of this, we’re rounding out this list with a tan leather western boot from Reformation. While this boot may not be made for a day on the ranch, it certainly looks the part and that’s enough for us. For a casually chic day, we’d style this with a coordinated top and bottom set from Tio Lee and coordinated hat and jacket from Halfdays.