How to Wear Cowboy Boots Without Looking Country (6 Unexpected Outfits)

I grew up on a farm with horses, Wranglers, and cowboy boots all around. But I don’t ride horses, and I certainly don’t live on a farm anymore, so when I wear cowboy boots, it can feel a bit like a costume. Like I’m pretending to be something I’m not — especially since one of my brothers wears boots to literally herd cattle and compete in rodeos. (And win, I should add.)

But I’ve decided that just because I’m not barrel racing, it doesn’t mean I can’t wear cowboy boots (or cowgirl boots, depending on who you ask). If anything, it’s a nod to how I was raised, which I’m quite proud of. So the trick has been finding outfits with cowboy boots that feel like me: polished, a little unexpected, and flattering.

I feel like summer is the perfect time to try cowboy boots. If you’re headed to a rodeo, demolition derby, or country concert, you need a outfit with cowboy boots that doesn’t feel like a costume. I have a whole roundup of 4th of July outfit ideas if you want more inspo for summer events, but this post is focused on the outfits that work for me whether I’m going to a rodeo or just running errands.

The obvious outfit ideas with cowboy boots (or cowgirl boots) are pairing them with flare, bootcut, or wide-leg jeans. But we can do better! Here are the ways I wear cowboy boots that don’t feel overly western, but instead, feel modern and more my style.

6 Unexpected Outfits to Wear with Cowboy Boots

1. With a Maxi or Midi Dress

Of all the options, this one is the most expected with cowboy boots, so to me it’s the least intimidating place to start. It can lean into western with a cowboy hat if you’re headed to a rodeo, or it can feel totally unique with a midi dress and no hat at all. The Everett Linen Dress is a good example of the latter. It’s so clearly not a western dress so the boots feel like a surprise rather than a theme. You can take nearly any midi dress you love and just add boots.

I have more ideas for pairing boots with dresses over at how to style boots with dresses.

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2. With Denim Shorts

This could easily feel cheesy or a little too young. (I’m 41, so I’m not pairing with short shorts.) For me to pull off this style, I had to find a way to balance the exposed leg with a little more coverage up top. These Abercrombie Dad shorts are my very favorite for denim shorts. I think the white with the brown leather cowboy boots feel even more unexpected than your traditional blue denim. I especially like this look paired with a button-up, but anything that gives more coverage up top would achieve the same effect. Think an oversized sweater, blazer, or even a jacket or cropped trench.

I’ve tried basically every denim short out there. My current favorites are all in this Abercrombie denim shorts roundup.

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3. With Satin Shorts

This might be the most unexpected pairing and perhaps my favorite lately. Satin shorts are a trend I couldn’t get behind for a while because they just looked like lingerie. But now that I’ve seen them styled in a way that feels more like me — with a blazer, an oversized sweater, or an oversized shirt — and less feminine and lingerie-ish, I like them a lot. And pairing them with cowboy boots makes them feel even more unexpected and lends a slightly masculine feel that I really like.

If you don’t have a go-to white tee yet, you can find my favorite white tees at this post.

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4. With a Mini Dress

This can easily lean cliched cowboy if you pair boots with a denim dress, so I prefer it with a white mini dress or a blue dress that’s not denim and has a little bit of intentional detail, like buttons. The Hill House Angie Dress is the white version I would wear with cowboy boots, it’s also one of my picks in my summer capsule wardrobe. And the Tuckernuck Navy Rhoda Mini Dress is the blue one I’m wearing in the photo above. Clearly not denim, same no-fuss look, and just enough shape from the buttons to keep it feeling put together.

I have more summer dress ideas over at casual summer dresses for moms.

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5. With Blazer & Boots

A blazer or trench coat is probably the last thing you’d think to pair with cowboy boots, but it’s a surprisingly fun combo. The oversized fit does the same thing as the sweater or white tee. It balances the boot without competing with it, and there’s something about the blazer specifically that makes the whole look feel more city than country, which is what I’m going for. And if you want to be even more casual, a baseball hat with this combination adds to the vibe.

6. With Linen Shorts and a Sweater

This is another option that’s simple to style, especially since it uses pieces you likely already have in your closet. I like this best with a monochrome pairing that lets the boots shine. It’s relaxed without being sloppy, and the boots turn what would otherwise be a pretty basic summer outfit into something that feels put together. Tan linen shorts with a cream or camel sweater is the version I want to try next.

Accessories for Cowboy Boot Outfits

When you’re finishing off your cowgirl boot outfits, accessories are really fun to think about. You can go all in on western accessories (think brown tones, turquoise, anything that compliments the boot) or you can go totally classic with the gold or silver pieces you already wear with everything else. Both work, and the classic route is what I find myself doing most.

Here are a few of my favorites across both directions. I have a full Mejuri jewelry review if you want to go deeper on the gold pieces.

• Mejuri Satellite Necklace. The most versatile thing I own, and works with every look here
• Mejuri Lab Grown Sapphire Huggies. Small enough to feel classic, not costume-y
• Mejuri Marquise Cut Studs. Simple, clean, easy
• Mejuri Charlotte Ring. 14k yellow gold, easy to stack or wear alone
• Baublebar Jane Beaded Necklace in Tiger’s Eye. This is the western direction. The brown tones pick up the color of the boots perfectly
• Z Supply Sunspell Polarized Sunglasses. Oval frame, goes with everything

FAQ

What jeans look good with cowboy boots, and do you tuck them in?

I don’t tuck. It tends to look bulky and reads more western than I want. What works best is a fitted or straight-leg jean that sits just over the top of the boot. It elongates the leg and keeps things looking clean. I’d skip the bootcut and wide-leg for this specifically; the whole point is to let the boot show just enough without making it the whole outfit.

Should you avoid double denim with cowboy boots?

I’d be careful. Denim on denim with boots can get very country very fast. If you love denim, stick to one piece: a denim jacket or jeans, not both.

What about a western belt — yes or no?

For me, no. A western belt with cowboy boots is a lot of western in one outfit. I skip it and let the boots be the nod to that aesthetic.

What tops look good with cowboy boots?

Anything that feels a little elevated or put-together: a blazer, an oversized button-down, a fitted knit. I’d avoid anything too frilly or puff-sleeved. It tips the whole look in a direction that’s hard to come back from.

Can you wear cowboy boots on a date or night out?

Yes, and I think this is one of the best uses for them. A midi dress or a mini dress with a little detail (buttons, a collar, something that gives it shape) with tall boots is a great date night outfit. It’s unexpected enough to feel intentional but not so trendy that it looks like…a costume. Skip the cowboy hat for a night out and let the boots do the talking.

Can you wear cowboy boots to work?

Yes, if your office allows it. A fitted trouser, a blazer, and a clean leather cowboy boot is a great combination. Stick to a boot without heavy embroidery for work and it’s an easy yes.