Dresses to wear with cowboy boots: Summer style guide

Wondering which dress to pair with cowboy boots? There's no dearth of options! Check out this list of twenty dresses you can wear with cowboy boots and experiment with, and make a statement.

Updated on May 11, 2023  |  12:55 AM IST |  591.2K
Bollywood celebrity style
Style of the season: Cowboy Boots

When it comes to the most versatile piece of clothing it's definitely dresses. With different silhouettes, sleeves, cuts and fits- there are a number of ways to style dresses up or down, and one of the most fashionable out of those ways is with cowboy boots! Whether you're headed for a fun day out in the sun or a night out dancing, there are a number of different ways to wear dresses with cowboy boots! So if you're convinced that cowboy boots are the next in thing, here are twenty cute dresses to wear with cowboy boots!


Tara Sutaria (Credits: Instagram)

20 Ways To Style Cowboy Boots With A Dress

1Mini Dress

First on the list of western dresses to wear with cowboy boots is a mini dress. If you wanna show off some leg, while keeping it casual yet sexy- mini dresses are the way to go. Paired with cowboy boots the duo is a win-win situation. Knee-high boots especially balance out a mini dress, and provide the contrast you need to provide a hint of skin, while keeping it cool and casual. 


Rakul Preet (Credits: Instagram)

2. Midi Dress

Somewhere between a maxi and a mini dress, a midi dress is a perfect balance between dressy and casual. If you're not sure about what your vibe is for a specific event, a midi dress is a way to go. With a multitude of options in terms of sleeves and neckline, the dress is flattering on most body types. Pair it with tights and ankle-length boots for a winter day, or skip the leggings for a summer day out on the town. If you're looking for cute summer dresses to wear with cowboy boots, there's no doubt that a midi dress is a perfect choice.



Radhika Madan (Credits: Instagram)

3. Maxi Dress

Maxi Dresses are perfect for any sort of casual outing. Whether it's spending the day at the beach unwinding, or basking in the sun at a picnic- this style is ideal for when you want to feel easy and breezy. Plus, it looks great with cowboy boots because even though hidden they give you the comfort and height needed to navigate an angle length dress. So if you're looking for long dresses to wear with cowboy boots, a maxi dress with comfortable boots and jewellery is the way to go

Sonam Kapoor (Credits: Instagram)

4. Bodycon Dress

One of the best dresses to wear with cowboy boots is a bodycon dress. It accentuates the best parts of you, and when paired with some classy boots, it highlights all the right curves. You can always elevate a bodycon dress with a blazer or a denim jacket, and jazz it up with some jewellery. Especially if you have an hourglass physique, and want to opt for something that cinches your waist perfectly, a well-fitted bodycon is the way to go. 



Kayan (Credits: Instagram)

5. A-Line Dress

One of the easiest breezy, and relaxed outfits to pair with cowboy boots is a classic A-Line Dress. An A-Line, as the name suggests, forms an A shape. It fits near the hips, and gradually flares out at the hem. Especially suited for pear-shaped bodies, when paired with cowboy boots- The a-Line dress accentuates your best features including your shoulders and waist. Great for when you're looking for casual dresses to wear with cowboy boots. An A-Line dress and cowboy boots are a great combination.


Sonam Kapoor (Credits: Instagram)

6. Wrap Dress

A wrap dress is a perfect summer essential that looks great with cowboy boots. It features a front wrap-around feature, by tying one side of the dress around the other with the help of a fabric that is clinched at the waist. Often featured in boho prints and summer silhouettes, wrap dresses look great on athletic bodies and even more so when paired with cowboy boots. If boho dresses to wear with cowboy boots are on your mind, - wrap dresses are ideal.



Priyanka Chopra (Credits: Instagram)

7. Trench Coat Dress

If spring dresses to wear with cowboy boots are on your checklist- a trench coat turned dress is a must have. A trench coat dress accentuates your legs, highlights your height and makes you look more toned out. Paired with cowboy boots your body will get an even more athletic touch- and look all the more evened out. Moreover, trench coat dresses in neutral colours are perfect for colder months where it’s all about keeping clothing and style to a maximum!

Priyanka Chopra (Credits: Instagram)

8. Blazer Dress

Perfect for when you're looking for formal dresses to wear with cowboy boots, a blazer dress is a right option for any sort of business occasion. Once paired with ankle-length boots, the entire outfit looks all the more stylish- and is great, especially for business casual occasions. Pair a bold-coloured blazer, with classic black boots to exude boss energy, while also keeping it classy and elegant overall.

Ali Bhatt (Credits: Instagram)

9. Sweater Dress

Nothing screams comfort and cosiness like an oversized sweater dress. If you're searching for dresses to wear with cowboy boots, winter edition- there's no better alternative than a casual yet stylish sweater dress. From vibrant knits to casual cotton blends, sweater dresses come in a number of different fits and forms. Moreover, you can pair them with knee-length or even ankle-length boots. Basically, a sweater dress is like a blank canvas. Style it according to the occasion and your style, jazzing it up with jewellery or keeping it simple with sneakers!



Priyanka Chopra (Credits: Instagram)

10. Shirt Dress

A more elevated version of a sweater dress, a shirt dress is a more formal variety of the class oversized tee dress. If styled right, it can be worn for a number of different occasions. Add a belt and pair of boots to keep it business-casual or accessorise it with a denim jacket and knee-high boots for a more elevated and stylish occasion. 

Sonakshi Sinha (Credits: Instagram)

11. T-shirt Dress

T-shirt dresses are the original trend setter when it comes to oversized dresses. The precedent to shirt and sweater dresses, T-shirt dresses are one of the most versatile pieces of clothing- great for all sorts of occasions. Pair them with knee high cowboy boots for a perfect concert fit or shorter alternatives for a comfortable day out in the city. You can play around with prints, patterns and colours- to either style it up or down depending on the occasion and your vibe!


Kiara Advani (Credits: Instagram)

12. Off Shoulder Dress

Off shoulder, dresses are great for those who want to accentuate their shoulders. They're often paired with cowboy boots to add an edgy touch. A ruffle on the sleeve, or ruched detailing paired with detailed jewellery, is great for a stylish night out on the town. If you want to experiment but are not ready to commit to a strapless style- an off-shoulder route is a way to go. Plus paired with boots, it looks all the more stunning.



13. Two Piece Dress/ Co-ord set

Ready to experiment even more, take a step forward from the common silhouettes and switch it up with co-ord set ensembles. Play around with different boot silhouettes in terms of footwear and some chunky jewellery including necklaces and earrings, to elevate your look and make it more playful and fun. Definitely high on the list of women's dresses to wear with cowboy boots, cord sets are a great way to step out of your comfort zone while trying to keep it fashionable.


Tara Sutaria (Credits: Instagram)

14. Sun dress

Sun dresses are the ideal route to take if you're looking for spring dresses to wear with cowboy boots. Play around with prints such as floral, stripes and polka dots to exude a vibe that is quirky and energetic. Tie the outfit together with classic cowboy boots, that will keep you comfortable and secure while you step out in the sun for a day filled with activities!

Priyanka Chopra (Credits: Instagram)

15. Satin Dress

A satin slip dress is the perfect way to look classy and graceful with minimal effort. This one-piece garment is free-flowing and elegant yet has a flattering silhouette overall. When paired with cowboy boots, a satin slip dress will give an authentic vibe. You can also pair it with a white t-shirt or white blouse underneath along with hefty boots, to dress it down and go for a casual yet layered, stylish look.

Shruti Hassan (Credits: Instagram)

16. Denim Dress

You can never go wrong with denim and since denim dresses are definitely trending this season, it's a great item to pair with classic cowboy boots. Whether you're opting for a mini bodycon denim dress or a mini A-line number, there's no combination that merges as well as boots and denim. So experiment with accessories including scarves, jewellery, sunglasses and hats- and tie the dress down with authentic cowboy boots.

Sonakshi Sinha (Credits: Instagram)

17. Tube Dress

If you're willing to go all the way, you can completely ditch the straps and sleeves, and opt for a classic tube dress. Not only will it highlight your assets and accentuate your curves, but a form-fitting tube dress with cowboy boots is all you need to turn the heat up. Opt for knee length cowboy boots, or ankle length ones and pair the tube dress with a leather jacket, to drive up the style quotient or keep it simple and sensuous with just the boots and dress!

Disha Patani (Credits: Instagram)

18. Skater Dress

A skater dress is a classic dress that can be styled however you want to. Pairing it with cowboy boots is the ideal choice because it adds a stylish touch to an otherwise basic silhouette. However, it's a cute and casual outfit, especially for the younger generation. So if you're looking for girl's dresses to wear with cowboy boots, a skater dress is a simple yet stylish option for you!


Malaika Arora (Credits: Instagram)

19. Tulle Dress

Another kind of dress that looks flattering, especially when it comes to younger generations, tulle dresses give you the princess feeling you deserve. Tulle is lightweight, soft and stunning in its own way- and when paired with neutral shades of boots looks extremely fashionable. The material, since it's sheer, looks delicate and subtle and so it's important to not go too grungy when it comes to footwear and keep it pastel and fun.

Deepika Padukone (Credits: Instagram)

20. Asymmetrical Dress

Last on the list of great dresses to wear with cowboy boots is the asymmetrical dress. Depending on the style of the symmetry, you can experiment with the style of your cowboy boots and play around with the size and shape. Whether it's an asymmetrical ensemble that is shorter in the front and longer at the back, or one that is one shoulder- they come in a number of different styles. However, each style if paired well can go with an asymmetrical number.


Rakul Preet (Credits: Instagram)

Cowboy boots are a must-have to build a capsule footwear wardrobe. They immediately elevate the look and can be accessorised with stocking, leggings, socks, jewellery and so many more items. Whether you're rocking a bodycon mini dress or a printed sundress, cowboy boots are the essential item you need to jazz things up. Now that you have this list of dresses to wear with cowboy boots, you can go all out and experiment with a number of different styles to make a statement!

Frequently Asked Questions

Is it OK to wear cowboy boots with a dress?
Yes! It's completely okay to wear cowboy boots with a dress, which is why we've mentioned twenty different dress silhouettes that you can experiment with!

Is it OK to wear leggings with cowboy boots?
Yes you can definitely style cowboy boots with leggings. In fact, sheer leggings or stockings is one of the most classic ways of styling cowboy boots. Especially if you're experimenting with wedding dresses with cowboy boots, or looking to wear boots for other modest occasions- leggings are the much needed accessory you need.

Do cowboy boots go with anything?
Almost anything! As long as styled well- cowboy boots can be paired with a variety of options including dresses, skirts, jumpsuits and more. In the list above we've experimented with a number of options including plus size dresses to wear with cowboy boots, as well as sleeker options.

What should you not wear with cowboy boots?
Athleisure is a big no-no. Sequins and cowboy boots also don't go well together. Fringe detailing too should ideally be avoided.

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About The Author

A student of mass communication and journalism, Anusha enjoys nothing more than cinema and couture. A fashion enthusiast, she



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