One of the trends I’ve been seeing is a style that’s actually quite classic. “Cowboy boots” are often associated with Nashville trips, and I’m not crazy about that idea as it evokes something rather… costume-y.
But I’ve always loved this boot style, especially when mixed with more casual pieces, so I’ll set aside that reaction. Today, I’ve put together some of my favorite ways to style them.
Wearing Cowboy Boots with Skirts
Pairing cowboy boots with a skirt is such a vibe. It creates this effortlessly chic look that’s both trendy and comfortable.
The boots are on full display with most skirt lengths, so you can keep the rest of the outfit minimal and still look amazing. Plus, a few well-chosen accessories can give you a total boho feel. Here are a couple of ideas for styling skirts and cowboy boots.
Mini Skirt with Bonderia Western Cowboy Boots
Image: Pinterest @girlsharestips.com
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There are so many ways to create chic looks with a mini skirt and cowboy boots. You can totally dress this combination up or down. Pairing the mini with a graphic tee gives you a chic street-style look.
On the other hand, wearing a denim skirt with a top or shirt and layering it with a coat helps you create a casual-formal style. This combo adds a bit of western-inspired flair to your outfit while keeping a youthful and trendy vibe.
Midi Skirt with Bonderia Western Cowboy Boots
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Putting cowboy boots with midi skirts results in an on-trend and chic ensemble. I think denim skirts are by far the most stylish choice, but you could also go for pleated or satin skirts.
You should aim for a length that falls below the knee, hitting around mid-calf. This allows the boots to peek out and adds a little vintage charm to your outfit.
For a top, you could try a cute corset, a simple blouse, a graphic tee, or even style it as a co-ord set like the girls in the pictures.
Maxi Skirt with ‘Casey’ Bukela Cowboy Boots
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Image: Pinterest @pradaandpearls.com
Image: Pinterest @pradaandpearls.com
When styled with maxi skirts, cowboy boots help create a free-spirited, bohemian look. Choose a flowy, lightweight maxi skirt that grazes the floor or hovers just above it.
A thigh-high or knee-high slit is a definite plus, making the whole look feel more appealing and sexy. The contrast between the rugged boots and the feminine skirt creates such an interesting and stylish juxtaposition.
Wearing Cowboy Boots with Jeans
A pair of cowboy boots with jeans or trousers and a blazer is the perfect street-style look. You can make this outfit super casual, or you can dress it up depending on the jeans and top you choose.
Here are a few ways I love to style these trendy boots with denim.
Bootcut Jeans with ‘Marian’ Bukela Cowboy Boots
Image: Pinterest @shopltk.com
Bootcut jeans were pretty much designed to go with boots, making them an ideal choice for this look. The slight flare at the bottom lets the boots fit comfortably underneath.
Just be sure the jeans have the right length, hitting the top of your heel or just a little longer. For the top, you can wear a graphic tee or a shirt. You could also layer the whole thing with a summer jacket.
Skinny Jeans with ‘New Kole’ Western Cowboy Boots
Image: Pinterest @fashionedforliving.com
This is such a popular and flattering option. Just pick out a pair of well-fitted skinny jeans that you can easily tuck into your boots.
This style really lets the boots be the focal point of your outfit and creates a streamlined, sleek look. For your top, you can go with pretty much anything, from a simple shirt to a ruffled top like the girl in the picture. Go cowgirl!
Cropped Jeans with ‘Lee Whiskey’ Bukela Cowboy Boots
Image: Pinterest @seaofshoes.com
If you’re going for a more trendy and modern look, think about wearing your cowboy boots with cropped jeans. A pair that hits anywhere from your low-calf to just above the ankle is perfect because it allows the boots to be completely visible.
This combo creates a fashion-forward and slightly edgy ensemble. You can pair them with a simple white tee, a graphic tee, or a blouse.
Adding a belt will enhance the look even more and bring in a touch of Western flair. Get some inspiration from the girl below.
Wearing Cowboy Boots with Dresses
When you style cowboy boots with dresses, it creates a boho look that’s both cute and cool. Just add some embellishments or fringe to the outfit, and you’ve got a bohemian vibe.
I love experimenting with different combinations to find a style that feels totally unique. Here are some chic ways to wear dresses of different lengths with cowboy boots.
Mini Dress with ‘New Kole’ High Western Boots
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Pairing a mini dress with cowboy boots can create a youthful and trendy look. I’d go for a dress that hits mid-thigh or even a little higher.
Think about choosing a flowy or A-line dress to contrast with the structured boots. You could also try a ruffled dress like the ones you see in the images below.
Maxi Dress with ‘Brooke’ Bukela Cowboy Boots
Image: Pinterest @girlsharestips.com
Styling a maxi dress with cowboy boots can add a touch of boho charm to your look. I’d opt for a maxi that has a high-low hem or a side slit so the boots can peek through.
This combination makes for an interesting visual contrast and gives your whole ensemble a unique flair. Take a little inspiration from the girl in the image below.
Midi Dress with ‘Bonderia’ Western Cowboy Boots
Image: Pinterest @stivalinewyork.com
Image: Pinterest @fashionista.com
Midi dresses and cowboy boots are perfect for a chic and effortless look. I’d aim for a dress that hits just above or right at the top of the boots. This creates a balanced and stylish silhouette, as the dress and boots transition seamlessly.
You can also add some accessories, like a hat, just like the girl in the picture below. Another chic way to style this is to layer with other pieces.
A long cardigan, denim jacket, or leather jacket over your dress helps create a cohesive look by incorporating the boots into the whole ensemble.