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Cute Summer Dresses To Wear With Cowboy Boots

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This post may contain affiliate links

No summertime dress is complete without a pair of cowboy boots (or two). Whether you’re going to your local farmers market or having a picnic in the park — slip on some sturdy cowboy boots and get ready to receive all the compliments. From city-sleek versions to rodeo-ready styles — Western-inspired boots are the perfect finishing touch to your dreamy summer dresses.

Traditionally, cowboy boots are paired with denim shorts or skinny jeans and a crop top. And while that outfit combination looks great — there’s no denying how a cute summer dress, cowboy hat, and western boot creates the perfect outfit for the warmer months ahead.

So, if you’re ready to saddle up and release your inner cowgirl, but you’re not exactly sure what cute summer dress to pair your cute cowboy boots with — we’ve cherry-picked the best dresses to help you hone your cowboy boot styling skills. From bright colors, puff-sleeves, to everyday dresses in exuberant prints — you’ll find the perfect dress below.

1. Cowgirl Chic

If there were a cheat code for putting together an effortlessly flawless summer outfit — a floral dress would be at the heart of the formula. Are you meeting with friends for an outdoor brunch? Or spending time with family? A voluminous silhouette will make getting dressed up easy. Plus, the best thing about puff-sleeve dresses is that they pair well with cowboy boots.

Elevate your puff-sleeve dress with a completely new stylish vibe by slipping on a pair of white cowboy boots. This outfit combination truly screams summer. Additionally, this effortless look requires little time to throw on. Just accessorize with an elegant ruched shoulder bag, small gold hoop earrings — and you’re done.

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Cute summer dresses to wear with cowboy boots

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2. Country Rock

Nothing feels more summery than an off-the-shoulder dress! They’re a great option for showing a little skin in the summertime!

Get ready to usher in the increasingly warm weather in style by dressing up in a shoulder-baring dress. The neckline is ultra flattering and the silhouette will make you look like a cute country girl. And now that social events are back, a Bardot dress will be your go-to ensemble to wear for summer activities.

If you want to be chic without being too attention-grabbing, invest in a summer-ready off-the-shoulder dress — and channel your inner Bridgette Bardot for a sexy look.

Equal parts formal and fun — you’ll have no problem going from day to night in an easy off-shoulder dress. When teamed up with black cowgirl boots and a leather jacket — your bardot dress will get an instant edgy finish.

Cute summer dresses to wear with cowboy boots

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3. Playful Hues & Sunshine

Since lockdowns are slowly easing, this season’s summer dresses are all about embracing all the feel-good colours. Swap those blue jeans and hit fresh on bright summer dresses, and anchor them with a great pair of square toe western boots.

Experiment with a plethora of candy-color hues and statement patterns for those summer nights or enviable tropical vacations — and you’re guaranteed to get a chorus of “where’d you get that?” requests.

A vivid summer dress might not seem like much, but the perfect one can cure all style problems. These romantic ruched, tiered, ruffle versions will be your unofficial summer uniform. From a midi dress to a mini dress, bright summer dresses allows for endless accessorizing options. Just swap those strappy heels for some brown cowboy boots, and top off with a vacation-ready straw bag, and your electric-hue summer dress will feel brand new every time.

Orange midi dress, straw bag and gold hoop earrings
Cute summer dresses to wear with cowboy boots

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4. Sassy & Summery

There’s an unwritten rule that long sleeve midi dresses are only a fall wardrobe staple — but who says that you can’t wear them in the summer, too?

Whether you need to cover up your shoulders because of workplace dress-codes, or because you feel insecure about your upper arms. Whatever the case, a long-sleeve dress will be your summer hero. Take your pick between party-ready styles, everyday silhouettes, and colorful prints (the options are endless! and there are many stylish ways to pull off this look in a chic way!)

For a fashion-forward and undeniably sophisticated look, opt for a charming long-sleeve number, and this will be your new favorite summertime dress. Round off your look with short cowboy boots to toughen up your gentle dress.

On unbearably hot days, show off those legs and go for a heightened hemline. And for cool summer days, throw on a breezy maxi long-sleeved dress.

blue and black floral print long sleeve dress, black shoulder bag, black cowboy hat
Cute summer dresses to wear with cowboy boots

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5. Effortless Elegance

Celebrate your re-entry into the world with a simple, easy-breezy (but no less stylish) formal dress. After a year of being accustomed to casual outfits like a jumper dress, sweatpants and loungewear, a simple formal dress is an answer to a polished post-lockdown look.

And you can nail this look in the easiest way! Wear your simple dress with oversized sunglasses, black Calvin Klein cowboy boots, and layer on a lightweight denim jacket for a chic and elevated look.

A formal and cute dress is truly a summer staple and the perfect choice for a summer soiree.

For instance, a feminine sundress will ensure you stay cool amid the heat, while a clean-cut short sleeve dress will be sure to get the job done. These staple pieces will make getting dressed up so easy, you will not have to put in a lot of time and effort to look instantly put together.

Related post: How to Find Your Own Classy and Elegant Style

Light blue A-line dress, Zara denim jacket and oversized glasses
Cute summer dresses with cowboy boots

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6. Farmers Market-Ready

Take a break from your usual neutral tones and go for statement pieces like Hawaiian and palm tree prints — your summer wardrobe would not be complete without one!

A tropical print dress will help bring the beach straight to you! They are perfect for summer weddings, or to go to your local farmers’ market. Simply pair your cheerful dress with your favorite pair of cowboy boots, and you have got yourself a great look.

White and black palm print  v-neck dress, round stacked statement earrings.
Cute summer dresses to wear with cowboy boots

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7. Off to the Rodeo

This summer is all about saddling up in country dresses and cowboy boots. They are perfect for showing off your inner cowgirl in a stylish way.

This season’s western dresses are classy, feminine, modern and alluring. So should your summer plans include visiting apple farms and attending country music festivals — a country dress will help you achieve the best bohemian style. From denim dresses, cold-shoulder sleeve dresses to ruffle v neck dresses –these silhouettes will help you embrace the optimism of the summer.

We highly recommend donning accessories that complement your country girl aesthetic — such as a cowboy hat and a great pair of cowboy boots.

Red chiffon maxi dress, pearl bangles and white cowboy hat.
Cute summer dresses to wear with cowboy boots

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Styling summer dresses with cowboy boots may initially seem tricky but once you follow these styling hacks, you’ll receive lots of head-turning compliments.

Now that you know what cute dresses to wear this summer, it’s time to start planning for some sleek beachwear for your upcoming vacation!
Up next: Classy Beachwear To Seriously Elevate Your Summer Style

Young white woman sitting in a grass field wearing a white long sleeve dress, thatched wide brim hat and leather cowboy boots
Cute dresses to wear with cowboy boots

Temwa Namandwa
Temwa is the fashion writer at My Chic Obsession where she covers everything from outfit ideas to the best styling tips . She lives for a good matte lipstick and LBD.