How to pull off the cowboy boots trend, five different ways

Cowboy Boots
Stephanie Montes, HelloGiggles

Fashion is a fickle beast, with new trends cropping up more often than you change your daily contact lenses. We know how hard it can be to keep up and even harder to figure out how to pull it off. With our series Try the Trend, we show you five different ways to make a current fashion craze work for you.

It’s no secret that all Western everything is having a moment right now, as proven by everything from the mainstream popularity of country star Kacey Musgraves and Lil Nas X’s “Old Town Road,” to the cowboy boots seen on Cardi B, Kendall Jenner, and Gigi Hadid. There’s just something irresistible about the current Yeehaw trend.

I, for one, have never worn cowboy boots in my life—mostly because I thought nothing in my closet would ever pair well with them—but on my first trip to Stagecoach, aka the country version of Coachella, I figured, when in Rome. So, I loaded up the tailgate of my cherry red Chevy Silverado (I’m getting in character here) with a standout pair of cowboy boots and a few staple pieces from my closet.

The boots I chose for my mission were this $65 pair from Akira.

I rode out to the desert, my country playlist blasting through the bumping sound system, a cowboy hat in the back seat, and lastly, the will to make the Western trend work for me.

Here’s how I styled my first pair of cowboy boots using essential items from my closet.

1With skinny jeans


A pair of high-waisted black skinny jeans are pretty much my daily uniform, so obviously I brought them along. To up my Stagecoach fashion game, I coordinated my black skinnies (get this cute pair from Reformation) with a plain white button-up, a bolo tie, and a Western-inspired belt. Finally, a pair of statement sunglasses ties the look together. It’s cowgirl-gone-Hollywood in the best way if I do say so myself.

2With a fancy maxi


Who said cowboy boots don’t go with an evening gown? To make this look work, I went with a simple silhouette (these boots are statement enough), in a complementary color. The best part is how the shoe peeks out from under the dress when I walk or hike up my hem, adding a fun element of surprise. (Grab this similar slip dress style from ASOS.)

3With a printed skirt


These boots are a statement accessory all on their own, but that doesn’t mean you should shy away from mixing prints. Just keep in mind: the rule of thumb for playing with patterns is sticking with prints that live in the same color family. You can find your own leopard print skirt at Nordstrom.

4With a feminine dress


You can’t ever go wrong with a pair of cowboy boots and a feminine, white eyelet dress. The dress already boats a prairie vibe that pairs perfectly with Western boots. (Get a similar look from Bloomingdale’s.)

5With denim cutoffs


Last, but not least, it wouldn’t be a cowboy-boot outfit roundup without a denim cutoffs option. It’s the easiest one to pull off—throw on a tee, slide on your boots and you’re ready to hit the hoedown. (Grab a cute pair of your own from Free People.)

As it turns out, cowboy boots fit right in with my current wardrobe. But above all, it took some extra confidence to pull these looks off. I don’t know if it was the Stagecoach vibes, the weekend spent driving a pick-up truck, or the non-stop country music that got me in the mood, but I think I found my new go-to statement boot.

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