Cowboy boots are one of those shoes that are always around, but don’t always feel chic—not unlike ballet flats, or Birkenstocks. The tide started turning, though, when Raf Simons sent them down the Calvin Klein runway for Fall 2017: Within the year, cowboy boots started popping up in collections by Isabel Marant (white, tan, and black leather styles with metal-toe caps), Fendi (with all-over logos), and fast-fashion brands like Zara and Topshop. Fast-forward to present day, and they’re at the very top of every fashion person’s shopping list. No matter where you look—runway, retail, street style—you’ll see a pair of cowboy boots, whether it’s an authentic, boot-scootin’ style or a sleeker, “inspired-by” type of design.

After a while, I’d come across enough cowboy boots that I decided it was time for me to come around to the trend (or, at the very least, give it a try.) It typically takes a few seasons for a trend to truly take off—it takes roughly the same amount of time for me to become convinced of its staying power. I’m in a committed relationship with my simple ankle boots, so the taller, more ornate cowboy styles felt like quite a departure from my style. But I was hitting that point of the season where I was feeling fatigued with my shoe selection, so I figured this fashion experiment would help get rid of this funk. Maybe I’d even come out of it with new outfit ideas for spring.

For a while, I admired the trend from afar, mostly in street style, and kept seeing a handful of styling tricks over and over again: cowboy boots worn with corporate suiting; cowboy boots with sweet flowy dresses; cowboy boots tucked underneath straight-leg jeans. But there’s a difference between dressing for Fashion Week and dressing for real life. I needed to find a way to wear these shoes that didn’t feel like I was dressing up as someone else—as someone who wears cowboy boots regularly, even.

So, I tried wearing cowboy boots for six days, wearing them in ways that felt in line with my personal aesthetic but still challenged me. The result? Well, you’ll have to scroll on to find out. Check out six ways to style cowboy boots (with affordable options!), ahead.

Laura Lajiness is a writer and editor based in New York. Follow her on Instagram: @lauralajiness.

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