50+ Cowboy Boots and Shorts Outfit Ideas: Your Year-Round Style Guide

Step into style across the seasons with cowboy boots and shorts outfits tailored for every time of year.

In this guide, we’ll walk you through a selection of looks starting with Casual Wear for everyday ease.

Next, we’ll amp up the vibe with Concerts, where music meets fashion. The Country Look will showcase rustic charm, while our Spring section bursts with new life.

As temperatures rise, our Summer styles will keep you cool, and when the leaves begin to fall, our Autumn attire will keep you cozy.

We’ll cap it off with Winter, proving shorts and cowboy boots can indeed defy the cold. Get ready to explore the perfect pairings for any season.

Shorts and Cowboy Boots Outfits for Casual Wear

Embracing the cowboy boots trend doesn’t mean you have to go full western.

There’s a sweet spot between Daisy Dukes and rodeo queen, perfect for those who love a casual yet chic vibe.

1. Start with a pair of navy blue shorts — think comfort with a hint of tailored elegance. Combine them with a crisp white sleeveless shirt, which brings freshness to your outfit.

Tuck the front of the shirt in slightly to add a touch of finesse. This look is perfect for a casual day out or a low-key brunch.

2. For the free spirits, a pair of brown shorts paired with a flowy top that sports a boho print is your go-to.

The laid-back nature of the shorts, combined with the intricate designs of the top, sets a relaxed yet intriguing tone.

Add a splash of personality with layers of turquoise jewelry and perhaps a fringe accessory to complete the bohemian allure.

3. Earth tones are your best friend when you want an outfit that speaks of subtlety and style.

Choose shorts in a soft brown or khaki paired with a simple, fitted white tank top. It’s a classic combination that feels effortless.

The cowboy boots in this ensemble should have a worn look to keep things rugged yet stylish.

4. For those who prefer a softer palette, light-wash denim shorts with a relaxed white tank top make for an airy, effortless choice.

It’s simple, it’s classic, and it works. The ensemble pairs perfectly with black cowboy boots to add a bit of edge to the softness of the outfit.

5. For those with a playful edge, try a cropped striped tee with your denim shorts.

The stripes add a fun pattern to the mix, and when paired with a set of black cowboy boots, it creates a casual yet eye-catching look.

Add a pair of sunglasses for that cool, mysterious vibe.

6. Lastly, channel some vintage charm with ripped denim shorts and a gingham top. This combo brings a touch of nostalgia that’s still very much in vogue.

Slide on some classic cowboy boots, throw on a wide-brimmed hat, and you’re festival-ready or set for a chic day out.

Image copyright Tecovas Boot Company | #CommissionEarned | The Jolene

Shorts and Cowboy Boots Outfits for Concerts

Concerts are your chance to show off your style and have fun with fashion. Here’s how to make shorts and cowboy boots your concert staples:

1. A pair of classic denim shorts teamed with soft tan cowboy boots creates an effortlessly stylish base. Layer on a loose white blouse for a relaxed fit that moves with the music.

A patterned kimono-style shawl draped over your shoulders brings a pop of color and character. Don’t forget a long pendant necklace and a stack of bracelets to add that indie artist touch.

2. Embrace the spirit of folk music with lace-trimmed shorts and timeless brown cowboy boots.

The intricate details of the shorts pair well with a simple peasant top, making for a harmonious look.

Embellish with a beaded necklace and a few bangles to jingle along with the beat. Sitting atop a log, you become part of the rustic scenery, ready for an impromptu jam session.

3. For those cool, urban concert vibes, rock a pair of structured shorts over opaque tights. This combination not only keeps you warm as evening concerts chill down but also amps up the style factor.

Slip into statement red cowboy boots that add a bold contrast to the darker tones of your outfit.

Up top, a polka-dot collared shirt under a sleek navy blazer fuses classic patterns with modern tailoring.

Complete this look with a pair of stylish sunglasses, and you’re all set to dance the night away in an outfit that harmonizes street style with stage presence.

4. Strike a pose in the backstage area with a high-fashion take on the cowboy trend.

Sky-high red boots paired with an oversized blue shirt strike a balance between edgy and casual. Add white denim shorts for a touch of summery flair.

A broad belt cinches the waist, offering shape and sophistication, and a round black handbag is both practical and trendy.

Top off the look with sleek sunglasses to keep you incognito as you rub shoulders with the stars.

5. Step out in white shorts and a tailored shirt for a sharp, concert-ready look. White cowboy boots extend the clean line, while a burgundy belt adds a pop of color.

Accessorize with a statement bag to keep essentials at hand and add visual interest. This crisp outfit is sure to stand out in a crowd.

6. If the concert calls for a more subtle yet sophisticated look, black is your go-to. High black cowboy boots paired with olive shorts deliver a sleek silhouette.

Keep it simple on top with a classic black tee, and let a unique pendant necklace be your statement piece.

Whatever your style, remember that concerts are about fun and self-expression. Let your outfit be your anthem!

Shorts and Cowboy Boots Outfits for Country Look

Embrace the rustic elegance of country style with a contemporary twist. These ensembles blend the timeless appeal of cowboy boots with the casual ease of shorts, creating chic and down-to-earth looks.

1. Rock a pair of classic denim shorts with comfortable tan cowboy boots for a go-anywhere country look.

Add a light, airy sleeveless top and layer on a fringe shawl to introduce some bohemian flair.

Accent the outfit with a bold turquoise necklace and a coordinating headband for a touch of color.

Carry a vibrant, patterned tote to pull the whole look together, perfect for a country market day or a casual outdoor gathering.

2. Embrace a simple, yet timeless country look with white shorts and a sleeveless denim top.

Brown cowboy boots bring in the rustic element necessary for any country outfit. Add a white cowboy hat to shield your eyes and finish the look with youthful charm.

3. Opt for a patterned, floral embroidered top with light denim shorts for a soft, feminine country vibe.

The embroidery adds a touch of craftsmanship that pairs beautifully with the simplicity of brown cowboy boots.

Complete this country chic look with a flower crown, making it perfect for a day spent in sunny fields or at a local farm event.

4. For those warm evenings, go bold with a vibrant, cropped top and white shorts. Light brown ankle cowboy boots keep the outfit grounded and easy to walk in.

Add a simple headband and some friendship bracelets for a laid-back, yet put-together country concert look.

5. A navy blue floral top with denim shorts is the perfect balance between casual and dressed up. Tuck the shirt in and fasten a decorative belt around your waist for added detail.

The cowboy boots should be a classic mid-calf height to complement the relaxed vibe of the shorts.

Whether you’re strolling through a country fair or kicking back at a backyard bonfire, these outfits combine comfort with classic country flair.

The key to nailing the country look is in the details — fringes, floral patterns, and touches of turquoise. So pull on your boots, and let your country spirit shine!

Shorts and Cowboy Boots Outfits for Spring

When spring blooms, it’s time to mix warmth with style. This season, blend the airy lightness of shorts with the statement of cowboy boots for a look that’s as fresh as the season itself.

1. Greet the spring sun with ivory lace shorts and classic tan cowboy boots. Pair this with a flowing white blouse for an ethereal touch.

Accessorize with turquoise jewelry to complement the earthy tones of the boots.

2. Stride into urban spring in tailored white shorts and a patterned navy blazer. Slip into sleek white cowboy boots for a crisp, modern look.

A tote bag in a neutral shade carries all you need for a day in the city.

3. Mix up textures with black lace-trimmed shorts and knee-high cowboy boots. A light blue shirt keeps it casual, while statement jewelry adds a city edge.

4. Soft beige shorts and a floral blouse are the epitomes of spring. Pair with white cowboy boots for a gentle, yet fashionable statement as you step into the new season.

5. Dive into spring with a balance of warmth and cool. A camel-colored blouse with voluminous sleeves offers a soft contrast to dark denim shorts.

Knee-high suede cowboy boots in a matching hue extend the warmth of the top. This outfit is a perfect match for spring’s unpredictable weather while keeping the look stylish and cohesive.

6. Embrace the country roots of cowboy boots with denim shorts and a folk-inspired embroidered top. Brown cowboy boots anchor the look in tradition.

7. Combine the delicate touch of lace with the rugged texture of denim for a spring look that’s both tough and tender.

A floral lace blouse tucked into distressed denim shorts pairs beautifully with classic brown cowboy boots. It’s a look that’s ideal for a casual spring day out.

Image copyright Tecovas Boot Company | #CommissionEarned | The Jamie

8. Embrace the freshness of spring in the city with a chic and modern ensemble. Pair crisp white shorts with a structured white blazer, adding depth with a brown belt at the waist.

Slip into snakeskin cowboy boots to add a trendy edge, perfect for a sunny brunch or a stroll through downtown.

Each outfit is a celebration of spring’s awakening, perfect for any adventure the season brings.

Embrace this transitional season with these diverse outfits that range from laid-back bohemian to sharp urban chic, all while highlighting the timeless cowboy boots.

Shorts and Cowboy Boots Outfits for Summer

Summer calls for outfits that can handle the heat while keeping you looking cool. Pairing shorts with cowboy boots offers a stylish solution that blends comfort with a dash of wild west flair.

1. Strike a pose on urban streets with tailored beige shorts and crisp white cowboy boots. Tuck a relaxed white shirt into your shorts for a smart casual look that’s summer-ready.

Accessorize with a large tote and sunglasses for a chic, functional outfit that can carry you from brunch to an afternoon at the museum.

2. Channel your inner bohemian with a pair of frayed denim shorts and intricate cowboy boots.

Add a white off-the-shoulder crop top to enjoy the seaside breeze and complement your look with a straw hat for that perfect beach-bound outfit.

3. Perfect for a road trip or a casual stroll, white shorts paired with a plaid button-up shirt tied at the waist offers a playful yet practical style.

Slide into some ankle-height cowboy boots to keep the look laid-back and ready for adventure.

4. Sometimes, less is more. Combine classic denim shorts with a simple white tank top for an effortlessly elegant summer look.

Black slouchy cowboy boots add a subtle edge, perfect for a summer night out with friends.

5. Embrace summer festival vibes with denim shorts and a white lace tank top.

Add a flowy, bohemian-style kimono, slip on some mid-calf cowboy boots, and adorn yourself with layered necklaces to dance the day away in style.

6. For those fun summer activities, a pair of short denim shorts with a splash of colorful plaid is your go-to.

The laid-back vibe of a knotted shirt paired with comfortable suede cowboy boots sets the tone for a relaxed, fun-filled day.

7. Match a pair of light denim shorts with a tie-front mini top for a look that’s flirty and rustic at the same time.

Calf-length cowboy boots in a soft suede material keep the ensemble grounded and comfortable, whether you’re on a countryside walk or stepping out for a casual summer date.

Shorts and Cowboy Boots Outfits for Fall

Fall’s cooler temperatures make for the perfect time to pair the ruggedness of cowboy boots with the playfulness of shorts, creating a blend that’s just right for the season’s crisp air.

1. A sophisticated take for those brisk autumn days involves pairing camel-toned shorts with a crisp white turtleneck.

Knee-high white cowboy boots and a statement trench coat with bold prints add an elegant yet edgy vibe.

Accessorize with a structured handbag for a fashion-forward fall look.

2. Get ready for the city’s fall scene with classic denim shorts and sleek black cowboy boots.

A simple black off-shoulder top keeps the look clean and versatile, while a leather jacket thrown over the shoulders adds just the right amount of attitude.

It’s the perfect outfit for an impromptu evening out.

3. For a cozy autumnal feel, style your shorts with a neutral-tone poncho or cape. Suede ankle cowboy boots in a soft beige will complement the outfit and add warmth.

This ensemble is ideal for those sunny yet chilly fall days, whether you’re out for a coffee run or a walk in the park.

4. Embrace the transition from summer to fall with denim shorts and brown leather cowboy boots.

A fitted, long-sleeve top in a warm hue captures the essence of the season and keeps you comfortable as temperatures dip. Add a leather satchel for a practical touch to this laid-back look.

5. A chunky knit sweater in a neutral tone paired with high-waisted denim shorts is a classic fall combination.

The oversized fit of the sweater adds warmth and comfort, while the high-waisted shorts highlight your waist, creating a flattering silhouette.

Complete the look with brown cowboy boots to add a touch of Western flair.

6. Nothing says fall like a plaid shirt. Tuck a plaid button-up shirt into your denim shorts for a laid-back, rustic look.

Add a belt with a statement buckle to cinch the waist and give the outfit some structure.

Finish off with a pair of glittery cowboy boots to add a fun and unexpected twist.

7. Choose an oversized cardigan in a soft, neutral color and pair it with brown denim shorts.

The contrast between the cozy cardigan and the structured shorts creates a balanced look.

Add a pair of classic brown cowboy boots and some layered necklaces for a touch of elegance.

8. A cropped floral top matched with cut-off denim shorts creates a playful and flirty outfit.

The cropped top highlights your waist, making it perfect for high-waisted shorts. Add a pair of tan cowboy boots and a wide-brim hat to enhance the look.

9. Layering a plaid shirt over a white tank top and pairing it with frayed denim shorts creates a rugged yet stylish outfit.

Add a belt to define the waist and white cowboy boots for a clean, coordinated look.

Top off the outfit with a wide-brim hat for a bit of sun protection and extra style.

10. For a romantic and glamorous evening look, pair a floral blouse with denim shorts and pink cowboy boots.

The combination of floral patterns and sparkly boots creates a feminine and eye-catching look. Add a necklace or earrings for a bit of extra sparkle.

11. Shine bright this fall with a sequin top paired with matching shorts. Add a jean jacket to layer up and keep warm as the temperatures drop.

Finish the look with glittery cowboy boots for a head-turning, cohesive outfit.

Accessorize with a belt to define the waist and simple jewelry to keep the focus on the sparkle. The outfit is perfect for evening outings and festive events.

12. Combine a bohemian flair with fall tones by pairing a patterned blouse with fringe-trimmed shorts. This outfit is perfect for nature walks and casual outings.

Add cowboy boots to keep the look grounded and stylish. Layer multiple necklaces for a touch of elegance and to draw attention to the neckline.

13. Make a statement with red leather shorts paired with a black turtleneck and a long trench coat. This outfit is perfect for city nights and sophisticated events.

The trench coat adds an element of mystery, while the black cowboy boots keep the look edgy and chic.

Complete the outfit with minimal accessories to maintain the bold aesthetic.

14. Embrace a retro look with a brown leather jacket and matching leather shorts. Pair this with a high-neck white blouse for contrast.

Brown cowboy boots and a belt with a bold buckle add a cohesive and stylish touch. This outfit is ideal for fashion-forward events and street style.

15. For a casual yet chic look, pair a white t-shirt with denim shorts and a light brown blazer.

This outfit is perfect for everyday wear and can easily transition from day to night. Add tan ankle cowboy boots for a touch of Western flair.

Accessorize with a wide-brim hat and sunglasses to complete the look. A backpack adds a practical and stylish element, perfect for on-the-go days.

Shorts and Cowboy Boots Outfits for Winter

Winter may bring the cold, but your fashion can still be hot. Shorts and cowboy boots in the winter? Absolutely. Pair them with the right layers, and you’ve got a bold look that defies the chill.

1. For a stylish and cozy winter outfit, black shorts paired with a soft beige turtleneck make a perfect combo. Sheer tights add a touch of elegance, while a plaid coat wraps you in warmth and sophistication.

Complete the look with brown cowboy boots for a classic yet modern vibe that’s perfect for snowy strolls.

2. Nothing says laid-back charm like a rust-colored sweater and denim shorts. The cozy knit adds warmth, while the distressed denim keeps things casual and fun.

Pair it with brown cowboy boots for a Western-inspired twist, and accessorize with a fringed bag and a wide-brimmed hat for that effortlessly cool, countryside vibe.

3. For a chic and warm look in winter, pair a chunky purple sweater with black shorts and an oversized knit scarf.

Tan cowboy boots bring just the right amount of Western flair, making this outfit perfect for winter markets or festive gatherings.

4. Black shorts and a gray turtleneck create a sleek foundation for a winter-ready outfit. Add a chunky green cardigan to stay cozy and stylish.

Slip on black cowboy boots to tie the look together, making it an effortlessly chic choice for casual winter outings.

5. For an elegant winter look, pair tweed shorts with a crisp white blouse. Add a warm, flowing brown cardigan to balance the soft neutrals.

White cowboy boots provide a bold, playful contrast, creating a standout outfit for festive evenings or winter dinner dates.

6. Make a bold statement in winter with red leather shorts paired with a sleek black turtleneck. Add a beige trench coat to tone down the drama while keeping it polished and chic.

Finish with red cowboy boots for a head-turning, confident look that’s perfect for city adventures or special occasions.

7. For an edgy yet casual look, pair light denim shorts with a black tee. Throw on a black leather jacket for that effortlessly cool vibe.

White cowboy boots add a fresh, modern contrast, making this outfit a great choice for a day out in the city.

Wrap it up

As we’ve journeyed through the seasons, it’s clear that cowboy boots and shorts are more than just attire — they’re a statement of versatility and style.

From the laid-back looks of summer to the layered ensembles of winter, these outfits prove that with the right pair of boots and a dash of creativity, you can keep your fashion game strong all year round.

Pull on your favorite cowboy boots, flaunt those shorts, and let your style speak for itself, no matter the season!

Grace

Howdy y’all! I’m Grace, a Western style enthusiast with over 5 years of experience. From cowboy boots to western gear, I’m passionate about all things Western and dedicated to helping you find the perfect style to suit your taste. Join me and my fiancé Jay Gatz as we explore the rich history and timeless appeal of Western fashion together!