How to Style Cute Outfits With Cowboy Boots: 7 Simple Everyday Looks

In this style guide, I’m going to show you eight cute outfits with cowboy boots. Cowboy boots have a bit of a bad rap for not being so easy to style. I’m here to show you that they are in fact, more versatile than you may think, and there are lots of ways to style them. Let's get started.


How to wear cowboy boots with a skirt

1. Cowboy boots with a mini skirt

First up, I’ve styled my Ariat cowboy boots with a mini skirt and a mustard yellow tank top. The skirt has embroidery on it in a similar tone to the top, so these two pieces work together seamlessly.


The cowboy boots finish off the look and create a cute and spunky outfit.

Cute dresses to wear with cowboy boots

2. Cowboy boots with a mini dress

Here, I’ve paired the dress with a flowy, tiered mini-dress, and what can I say? This outfit is so simple and trendy.


The burgundy dress works really well with the russet shade of the boots as they are analogous colors.

Women's outfits with cowboy boots

3. Cowboy boots with a midi skirt

When you want to cover up a bit more, a midi skirt is a smart choice. Here, I’ve paired a simple black pencil skirt with a cozy cream knit sweater. For a laid-back look, I’ve tucked it in at the front and left the rest of it untucked.


Of course, the brown boots work well with the black and cream; here, we have a neutral color scheme creating an effortlessly chic outfit.

Cowboy boots with shorts and a blazer

4. Cowboy boots with shorts

For more of a fun look, I’ve paired the cowboy boots with some denim shorts, a white tank top, and a pink blazer. The blazer brings a more formal edge to the casualness of the shorts, and dusty pink is one of my favorite colors.


This outfit gets the thumbs up from me, and I would wear it on a day out with friends.

Best jeans to wear with cowboy boots

5. Cowboy boots with jeans

In this next look, I’ve styled the cowboy boots with some high-waisted jeans, and this combination gives me Western vibes.


The tucked-in button-up shirt also plays into this aesthetic, and I feel like this look is a nod to how cowboy boots were originally worn in the Old West.

Styling jeans over cowboy boots

Here, I’ve styled them with flared jeans and a burgundy sweater. In this outfit, the jeans fall over the top of the boots so that only the bottom part is visible.


Alternating between having the whole boot showing or just the bottom part gives you more options when it comes to styling cowboy boots.

Can you wear cowboy boots with a romper?

6. Cowboy boots with a romper

In this look, I’m wearing a black button-down romper, and this again is one of those really easy outfits that you can throw together in no time.


Because cowboy boots already have some personality and character to them, you don’t want to overdo it with the rest of the outfit. A simple romper like doesn’t steal the limelight from your footwear.

Cute outfits with cowboy boots

7. Cowboy boots with a floral dress

Last but not least, I’ve styled the cowboy boots with a midi-length floral dress that has a slit in the front. The combination of leather boots with florals gives off the perfect spring vibes.


The boots give you that warmth for when the weather is still a little chilly, and the floral print perfectly ties in with the flowers blooming this season.


Cute outfits with cowboy boots

I hope you now have some inspiration for how to wear cowboy boots. As I mentioned, because they already have some character to them, you can leave the rest of your outfit quite minimalist, and you’ll still look stylish and put together.


If you haven’t worn cowboy boots before, now is your time to give them a try! What do you wear your cowboy boots with?

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