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Awesome Dresses to Wear with Cowboy Boots: 17+ Styling Ideas

Awesome Dresses to Wear with Cowboy Boots: 17+ Styling Ideas

Women have hundreds of dressing styles that are derived from just tops, pants, skirts, and dresses. And the amazing thing is, all of those things can be worn with cowboy boots perfectly.

Needless to say, cowboy boots can turn you into a fancy cock full of personality but also without a lack of professionalism (as long as you know some rules of coordination between those items).

Many of us are tired of figuring out what top, pants, or skirt to mix together to wear cowboy boots. Let’s just pick a dress that requires slipping over your head in a few seconds then you’re ready to go outside or do whatever you want afterward.

A woman wears a red dress with cowboy boots

A dress won’t make you look “out of place” on the whole, unlike when you choose a shirt that doesn’t match with pants or skirts. Dresses are usually designed uniformly from the top down with the top and bottom details linked together.

Because of this, you have completely achieved the ton-sur-ton effect of 2/3 items when combined with the cowboy boots that we have mentioned in the previous posts.

For that reason, getting your outfit up with cowboy boots is way more simple, fast as well as saves a lot of money and time.

Woman wears cowboy boots with dresses

Can you wear Cowboy Boots with Dresses?

Yes, definitely. If wearing cowboy boots with jeans and a T-shirt makes you look like a fabulous cowgirl from Texas, wearing these boots with a dress will instantly turn your appearance into a girly but edgy style and still look attractive in your own way.

Cowboy boots bring a strong personal style. So, even when combined with ruffled or cumbersome embroidered flowery types of dress, you still become dynamic and swagger but courteous in the eyes of everyone.

A woman wears The Paige cowboy boots with dresses

The Paige Cowboy Boots | Click image for more info on Tecovas | #CommissionEarned

That’s why so many folks have made this combination of wedding dresses and cowboy boots as a wedding dress code. What could be better than to make the special atmosphere of the most important day of your life unforgettable in such an impressive and fashionable way?

More than just casual fun or parties, if you need a little more professional look for your purposes when wearing it with a dress, a pair of ankle cowboy boots is a safer choice. These boots ensure a flattering heel height and are courteous enough for you to look your best.

Less embroidery and embellishments will make you look professional without being way too bland or monochromatic.

A woman wears long red dress, coat and cowboy boots

What types of Dresses can you wear with Cowboy Boots? 14 Ideas

For women, I can count up to a few thousand different styles of dresses, which is admirable! Women even create new dresses simply by adding an element of one style to another, and Boom, a new dress style is born!

Therefore, you will never be short of ideas on what kind of dress to wear with cowboy boots. (I’m afraid you have too many things to mix and match!). Here are the most popular dresses to wear with cowboy boots:

1. Midi Dress

Midi dresses are the most popular form of dress because they have a no-frills design with calf-length and biceps sleeves. You can wear it at home or out on the street or do whatever that still ensures the best politeness and courtesy.

A woman wears dress with cowboy boots

When wearing a midi dress with a pair of black or brown cowboy boots, confidently express your personality with any dress color and texture you want.

A woman wears dress with black cowboy boots

Tip: A slit below the dress will reveal your legs and boots, making you more attractive and impressive.

A woman wears floral midi dress with suede cowboy boots

2. A-line dress

A-line dress is the second most popular dress style, just behind the midi dress. It often has the bottom designed to extend from the top down wider than the design of the midi dress.

So even if you have a big butt or wide hips, the dress can still fit and correct your body’s flaw (if you consider it a flaw).

A woman wears A line dress with cowboy boots

The dress also balances slender bodies to be less slim. When wearing cowboy boots you will still feel a certain comfort by the width of the bottom of the dress.

A woman wears lace dress with leather jacket

This combination gives you a stylish and ready look for either a picnic or a shopping trip.

3. Mini Dress

A mini dress is another type of dress that pretty girls love to wear. Because it helps show off her long slender legs and a perfect hourglass figure with the dress length usually just above the knee.

Womens wear long coat with cowboy boots

When worn with cowboy boots and especially over-the-knee boots, the footwear will help cover part of your legs to make the outfit look less “showy” if you’re afraid someone is going to mess with you.

A woman wears over the knees cowboy boots with mini dress

Overall, you will have a very stylish, dynamic, and cowgirl look for a party, a picnic, or even dating with a mini dress, cowboy boots, and a wide hat.

4. Pleated Dress

Pleated dresses and cowboy boots are a great match. They mix fancy and casual in a nice way. The pleats bring elegant style to the dress while the boots add a tough and sleek feel.

a woman wears pleated dress with cowboy boots and hat

Whether it’s a short or long dress, this combo looks good and feels comfortable. It’s just right for outdoor events or a simple relaxed day.

A woman wears lizard cowboy boots with pleated dress

A pleated dress with cowboy boots is quite stylish, perfect for someone who likes a mix of city and country styles.

5. Layered Dress

Layered dresses paired with cowboy boots create a unique and stylish look. The layers add a playful touch, making the outfit feel light and airy.

A woman wear boho dress with cowboy boots

When I pair my layered dress with cowboy boots, it gives off a cool, bohemian vibe. It’s a combination that works for so many occasions, from a day out with friends to a formal evening event.

The boots add a bit of ruggedness that contrasts nicely with the softness of the dress. This look is all about balancing comfort with a touch of adventure in your style.

6. Off-the-shoulder dress

The Sadie Cowboy Boots

The Sadie Cowboy Boots | Click image for more info on Tecovas | #CommissionEarned

A very playful style, the off-the-shoulder dress gives a fresh and youthful feel that most girls aspire to.

With the sleeves falling off the shoulders and dress length above the knee, wearing them with cowboy boots or ankle boots will both reveal part of your legs as well as beautifully decorated boots.

A woman wears red dress with red cowboy hat and red cowboy boots

However, I suggest you choose a dress that is uniform in color from top to bottom when paired with cowboy boots. Don’t make your outfit and footwear become 3 distinct pieces that have nothing to do with each other.

7. Maxi dress

A maxi dress is a typical dress for beautiful sunny beaches or semi-formal to formal parties. It has the same design as an A-line dress and midi dress but get a floor length.

A woman wears boho dress with black cowboy boots

A maxi dress is sewn to fit the body shape around the waist and the details on the top and bottom are freely and gracefully, making the wearer feminine and extremely attractive.

If you intend to take impressive and fashionable photos by the beach, wearing a maxi dress with cowboy boots will make you stand out.

A red maxi dress in chiffon fabric will turn you into an unmistakable Boho girl.

Women wear prom dress with cowboy boots.

8. Wrap dress

A woman wears purple midi dress with cowboy boots

A wrap dress is particularly recognizable by wrapping around the waist and possessing a tie-down waistband in the front. In fact, they also adopt mini, midi, or A-line skirt lengths.

But one thing to keep in mind is that the waist closure can make the overall dress a bit cumbersome depending on the length of the strap, so it is better to choose a pair of cowboy boots with a simple design (little decoration or slight embroidery) to mix with this dress. Therefore, it can balance the overall outfit effectively.

9. High-low dress

Like the high-low skirt, the high-low dress stands out with the design of the front being lower than the back, creating a feminine and floating cut-out for any wearers.

A woman wears lace dress with brown ankle cowboy boots

The dress is extremely flattering and makes anyone’s legs slimmer and longer.

When paired with this dress, choose a pair of high-heeled cowboy boots but keep in mind that do not let the boots get swallowed up inside the front part of the dress.

If the front part is short above the knee, a pair of high-heeled Buckaroo will be the perfect match to make you a queen at any party.

10. Sweater Dress

An indispensable choice for winter, a sweater dress. This is essentially a sweater with a sewn edge that extends to or below the knee, creating the shape of a dress. It usually has a wide body shape with a high collar and long sleeves.

Women wears sweater dress with cowboy boots

They are comfortably warm. Therefore, wearing the dress with cowboy boots will double that coziness for you in winter.

A woman wears white sweater dress and brown ankle cowboy boots

If you wear a striking red sweater dress, you should choose a pair of boots in basic or neutral colors.

A woman wears red sweater with knee high cowboy boots and beret

11. Shirt dress/T-shirt dress/Denim dress

Just like the sweater dress, the shirt dress/T-shirt dress/denim dress has a similar design with the hem being sewn above or below the knee and becoming the shape of a dress. The biggest difference is the materials that make up the dress.

A woman wears button front dress with black cowboy boots

Shirt dresses are usually made of synthetic fabrics with smooth or glossy, breathable effects while t-shirt dresses are made of stretchy and sweat-wicking cotton fabrics.

A woman wears red cowboy boots with button front dress

Wearing these two styles of dresses with cowboy boots will create a super unique and impressive style for you.

12. Pencil dress

A pencil dress is a typical business dress with a one-piece design from top to bottom with a slim fit and usually knee length. It makes for an extremely professional look and can be a bit formal if you’re about to wear it for a casual party.

In this case, you can choose a pencil dress with mid-thigh length with fringes. Adorn your legs with mid-calf cowboy boots to rock any event!

A woman wears fringle dress with a pair of cowboy boots

On the other hand, if you wear a pencil dress to work, style it with ankle cowboy boots. As mentioned above, ankle boots help your overall style become leaner and more flexible in business.

A red pencil dress with a pair of ankle cowboy boots will definitely give you a sense of a powerful bossy attitude.

A woman wears black cowboy boots with red dress

13. Bardot dress

It is a very unique and playful dress that I would love to introduce to you. I believe many of you have seen this dress but probably don’t know its real name.

A woman wears lace dress with cowboy boots

The dress is named after Bridgette Bardot. She inspired a dress with a hot design with puffy and off-the-shoulder sleeves.

As for the structure, the lower part of the dress is designed to spread downwards widely, but with a thin outer flap to reveal the inner leg mysteriously and seductively.

A woman wears lace dress with brown cowboy boots

Therefore, when wearing cowboy boots, you should choose a boot with a great high heel and sleek leather, and streamlined design rather than heavy embroidery details to balance the overall outfit.

14. Ball Gown dress

A woman wears cowboy boots in her wedding
Whoever said a ballgown dress couldn’t be worn with cowboy boots, must have no idea about women cowboy boots’ culture. Cowboy boots break the image of a bride on her wedding day having to be fragile and in need of protection.

If your ball gown only reaches the calf, the wonderfully decorated boots will be revealed beautifully. It is even more flattering when you wear them with a white high-low ballgown dress.

What Style of Dress Goes Best with Cowboy Boots? 3 Ideas

No matter what kind of dress you wear with cowboy boots put them together based on a certain style rather than on a fad.

Actually, cowboy boots can make you look very basic, but can also dress you up like a very clunky and sloppy homeless guy if you just pick the wrong items to pair with.

Therefore, to create the most balanced overall outfit for you for any purpose, we have gathered around these 3 fashion styles that are best coordinated with cowboy boots.

1. Bohemian

A woman wears floral dress with a pair of suede ankle cowboy boots

Bohemian style or Boho can be considered a top priority when combined with cowboy boots. Boho dresses are often inspired by the motifs of A-line, high-low, maxi, or even off-the-shoulder dresses.

Women wears cowboy boots and maxi dress with modern style

They are made with a blend of lace, polyester fabric, or rayon to give the dress a nomadic and feminine feel. Brocade prints or small flowers printed on the skirt are special highlights for this fashion style.

a woman wears dress with The Daisy suede boots from Tecovas

The Daisy Cowboy Boots | Click image for more info on Tecovas | #CommissionEarned

Bohemian dresses and cowboy boots both inspire freedom and have a bit of wildness as well as a bit of vintage, you can wear this outfit to Bohemian-style parties, outdoor picnics, leisurely walks on the beach/street, arty photo shooting, and shopping.

2. Classic style

Classic fashion style has a long history of establishment in the fashion industry. Classic fashion style is a symbol of simplicity, elegance, courtesy, and femininity. It also has another name, Parisian style, referring to the place where it was born “the fashion capital of Paris”.

Classical dresses must first of all be designed without flamboyant, ostentatious, and monumental in terms of materials, colors as well and forms. They will follow the most basic, neutral, and delicate fabric tones, but are no less romantic and attractive to the eyes of others.

A woman wears dress with cowboy boots

This classic style celebrates the curves of the body. Therefore, it still respects the traditional textures and structures.

Wearing a classic dress with cowboy boots can be a break that many people cannot accept. But I personally feel that this is a combination that transcends all limits and prejudices.

Let’s just opt for ankle or knee-high cowboy boots that have smooth, sleek leather texture and neutral designs that fit comfortably around the leg.

3. Business Casual Style

A woman wears white ankle cowboy boots with plaid dress
Business casual is a term for a style of clothing that is less formal than business negotiation suits but still aims to create a professional impression and demeanor of businesswomen.

This style is applied in-office fashion often with A-line dresses that reach to the calf and long sleeves. Dress designs can vary from a midi dress, wrap dress, or even high-low dress but they must possess rigid, discreet, and subtle cut-outs.

A woman wears black wrap dress with cowboy boots

When wearing this style with cowboy boots, opt for ankle boots with minimal embroidery and base colors like black, brown, or deep Burgundy red on a polished leather base.

Other Questions

1. Do Ankle Boots Look Good with a Dress?

Yes, they are. Ankle cowboy boots make you look more active and neater than wearing high-collar cowboy boots.

Women wear long coat with western ankle boots

The design of ankle boots is simpler and less burdensome in decoration or embroidery due to the limited space on the boot shaft. So, you can still look very professional and polite when wearing a dress in business.

However, everything has its downside.

Ankle cowboy boots may not make your “cowgirl” style stand out in the crowd as much as wearing a pair of traditional cowboy boots or Buckaroo. If your goal is to take the spotlight as much as possible in this style, high-collar cowboy boots are still a better choice.

But if you need boots that can be worn anywhere, anytime, and in any situation then ankle cowboy boots will be a more versatile choice to wear with a dress.

A woman wears ankle boots with split maxi dress and wide brim hat

Also, ankle cowboy boots can make your legs look longer if you have short legs while wearing traditional cowboy boots will seem to swallow up your legs for a  shorter look.

If you have a muscular or very thick calf, ankle boots can fit any leg size (simple because they don’t reach your calves).

A woman wears maxi skirt with cowboy boots

2. How to Wear Cowboy Boots with a Dress?

To look your best when wearing a dress with cowboy boots, there are a few things you need to know:

 Purpose of your dressing

This is the most important because it determines how effective that style and sense of successful communication can be. Imagine if you show up at your friend’s party in Gatsby style with a business shirt and casual pants.

Well, you really look like a loser and everyone else looks at you like an alien. You also don’t really have the confidence to start a conversation with anyone, which sucks! So, what is the purpose of you wearing a skirt with cowboy boots, you need to make it clear first to pick proper items altogether.

 Design of cowboy boots

A woman wears cowboy boots and is standing on the trees

Often, we will choose a dress to match the cowboy boots instead of choosing boots to match that dress. Simply because most of us have more than a few dresses while probably only owning 1-2 pairs of boots.

Therefore, the design and color of cowboy boots are very important to coordinate with the dress for the best fit.

If your boots have basic colors like black or brown, they can match any dress color.

But if you have a pair of red, blue, and yellow cowboy boots with heavy embroidered patterns on the shaft, you should choose a dark or neutral dress like gray, black, or white for casual or you can wear it with a ruffle or sequin dress to take to the stage (for the show or performance).

Again, it depends on your purpose.

3. How do you wear Cowboy Boots with Skirts or Dresses?

Wearing cowboy boots with a dress is usually not as picky as it is with a skirt. You just need to choose the style of the dress, the color of the dress, and the accessories to go with it (like hats, bags, and jewelry) to create a certain style that suits your purpose.

For example, when going on a beach vacation, you should mix a pair of knee-high cowboy boots with off-the-shoulder floral printed dresses or Bohemian nomadic patterned dresses.


But if for business purposes, you should choose a pencil dress or A-line dress in less stretchy material and wear it with plain, less embroidered ankle cowboy boots.

A woman wears black cowboy boots with dark blue dress

If you wear cowboy boots with a skirt, you will have to consider the color combination of the shirt, skirt, and footwear so as not to turn yourself into 3 pieces of unrelated colors.

Use the principle of “ton sur ton” to combine tops and skirts with cowboy boots, in which at least 2 out of 3 things have the same color. All that remains is to choose which shirt to go with which skirt for your own purposes.

A woman wears brown cowboy boots with a pleated skirt

Before you leave

Picking a dress to wear with cowboy boots is not even difficult. Girls, you have thousands of dress types out there. But what we want to remind you is to pick something that creates a style.

That is the best way not to waste your hard-earned money on expensive cowboy boots when it comes to finding the best dresses to wear with the boots.