How Our Fashion Editor Is Styling Cowboy Boots for Fall

I have to be honest: When cowboy boots first gained popularity in the fashion sphere last year, I rejected them with every fiber of my being. As a born-and-bred Chicagoan who only listens to country music twice a year (sometime between June and July while I’m on a boat, specifically), they didn’t feel like something that I could ever pull off—nor something I really wanted to try to pull off.

As I saw more and more girls with style I admire pop up on my Instagram feed wearing cowboy boots, my icy exterior slowly started to melt, and I noticed myself wishing I had a pair in my closet. They just had a cool, effortless vibe that brought an entire outfit to life in a way that most shoes aren’t capable of alone (Princess Diana knew all about that). As I started planning my fall wardrobe for 2022, I decided it was time: I wanted cowboy boots, but they needed to be the absolute perfect pair.

My search began for boots with two must-have qualities: I wanted them to feel wearable in my day-to-day life, and I wanted them to be something I knew would last. The ones that stopped my investigation in its tracks? Tecovas. One peruse through their Instagram, and I was sold. Tecovas started out of a love for the traditional, timeless craftsmanship of cowboy boots with a focus on quality. Each pair is handcrafted in over 200 steps, but without retailer markups, they’re double the quality of similarly-priced boots at half the cost.

After many weeks of debate, I decided on my perfect boots, and out of the gate, was completely in love. The second I took them out of the box, I could feel that they were a quality that you just don’t come across often. They’re comfortable, beautiful, and are that kind of piece you just feel like you’ve had in your closet forever; a staple that works its way into your rotation and never leaves.

As we’ve entered August and my mind has gone exclusively to fall fashion, I’m planning on my Tecovas being a staple of my looks. Here are three ways I’m planning on styling them as soon as hot Chicago temperatures cut me a break:

With denim shorts and a blazer

This is a look I’ve had in my mind for quite some time now, and boy oh boy, is it as good as I planned on it being. I’ve been obsessed with these long, oversized denim shorts this summer. They feel a little bit more stylish than my traditional shorts, but since they aren’t tight, don’t veer anywhere near a bermuda situation. With a fitted shirt, blazer, and my cowboy boots finishing it off, it feels concrete cowboy in the absolute best way.

With jeans and a button-up

In my humble opinion, one of the coolest ways to style cowboy boots is with a slim, straight jean (not to be confused with a skinny jean) tucked in. The jean should look a little loose and bunched up, which is why I avoided styling them with anything too tight.

The result of this feels chic and wearable and is a fun take on my typical white button-up, jeans, and fall booties outfit uniform. I’ll definitely switch the top around as the jeans-and-boots combo can be paired with literally anything, but I love how effortless it is to pair it with a tucked-in, oversized poplin shirt.

With a dress and sweater vest

If there’s one thing I love when I’m styling an outfit, it’s a good juxtaposition, and that’s exactly what’s going on here. The outfit itself has an uber-preppy vibe, but the cowboy boot is an unexpected pairing that makes it avoid feeling like I’m just channeling Blair Waldorf. The contrasting combination is one that I’ll be styling all season, especially with dresses, as I love how much it allows the boots to be the focal point of the look.

More cowboy boots we love

This post is sponsored by Tecovas, but all of the opinions within are those of The Everygirl editorial board.