Cowboy Boots with Shorts – 14 Chic Outfits for Day or Night

Cowboy boots are having a major fashion moment right now. Typically associated with country music festivals and the American southwest, cowboy boots are now being styled in fresh, modern ways for everyday wear.

One of the hottest trends is pairing these Western-inspired boots with shorts. From classic denim cutoffs to flowy midi shorts, cowboy boots add an instant cool-girl edge to any warm weather look.

Ready to kick up your shorts game? Keep reading for 14 fabulous cowboy boots with shorts outfits, along with ideas for where to wear each look and tips to recreate the style.

1. Casual Coffee Date

Casual Coffee Date
credit: instagram/briannesikorski

This monochromatic outfit looks chic and pulled-together for grabbing an iced coffee with your crush. The metallic silver cowboy boots add eye-catching contrast against the all-black ensemble.

To recreate this look, opt for a fitted grey tube top and black denim shorts. Add some edge with a black faux leather moto jacket draped casually over the shoulders. Carry just the essentials in a small black chain-link crossbody bag.

Finally, slip on a pair of metallic silver cowboy boots to pull the outfit together. This glam-meets-edgy vibe is perfect for a casual first date at a hip local cafe.

2. Brunch with Friends

Brunch with Friends
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Nothing says Sunday Funday like brunch with your besties! This sweet and feminine outfit is perfect for long, leisurely meals spent catching up over bottomless mimosas.

Start with a delicate white lace-trimmed tank top tucked into your favorite denim cutoffs. Add a dainty necklace with a minimalist pendant for a touch of shine.

Finish the look with pretty pastel pink or blue cowboy boots. Soft makeup in neutral tones completes this daytime date ensemble.

3. Music Festival

Music Festival
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Heading to Coachella or Austin City Limits this season? Stand out from the crowd in this boho-chic festival outfit.

Start with a breezy kimono-style cardigan in colorful patterns and intricate designs. Layer it over a simple white spaghetti strap tank and high-waisted denim shorts. This creates a stylish desert-ready look made for dancing all day long.

Next, slip on a pair of knee-high brown leather cowboy boots to embody that effortless Indio style. Don’t forget your floppy sunhat and a hands-free crossbody bag to complete the laid-back festival vibe.

4. Happy Hour

Happy Hour
credit: instagram/haleighwhitcraft

Drinks after work call for easy, casual pieces that still look put-together. Start by swapping your office trousers for frayed light denim cutoffs to get into relaxation mode.

Next, throw on an opaque black cami and layer a black sheer blouse on top. This creates dimension while keeping things office-appropriate.

Finish with sleek over-the-knee brown leather cowboy boots and a black leather crossbody bag for happy hour fun. This effortless outfit transitions seamlessly from the office to the bar.

5. Backyard BBQ

Backyard BBQ
credit: instagram/taylortippett

Backyard BBQ season is nearly here! This laid-back summer outfit is perfect for soaking up the sunshine all afternoon. Start with an oversized blue graphic tee for that perfect slouchy, relaxed vibe.

Next, slip into a pair of light wash denim cutoffs, made soft and distressed from years of wear. Make sure they hit mid-thigh for a leg-lengthening look.

Then ground the look with a pair of commanding tall black leather cowboy boots. This outfit keeps things cool and casual for a backyard bash with friends.

6. Music Venue

Music Venue
credit: instagram/teacherintulle

Ready to rock out at a concert or intimate live music venue? This edgy outfit brings just the right amount of attitude. Start with a simple ribbed tan tank tucked into high-waisted black denim shorts. Cinch the shorts with a black leather belt to create a flattering silhouette.

Next, slip into versatile knee-high black leather cowboy boots. Their lightweight durability makes them perfect for hours of dancing.

Finish with a boho-inspired patterned crossbody bag with long fringe. This effortlessly cool ensemble is ready for a night out!

7. Rodeo

Rodeo
credit: instagram/justalexbennett

Yeehaw! Channel your inner cowboy (or cowgirl) at the rodeo in this all-white ensemble. A crisp white blazer gives polished structure to sporty mid-thigh shorts.

Look for shorts with a moderate inseam to maintain modesty while riding the mechanical bull. Finish the rodeo-ready outfit with versatile brown leather cowboy boots.

Don’t forget your Stetson hat to complete the downhome country look!

8. Park Picnic

Park Picnic
credit: instagram/izzzxie

Picnics in the park call for outfits that are casual, comfortable, and hamper-friendly. This breezy look can be thrown on at a moment’s notice.

Start with a flowy white blouse in a lightweight material, ideal for hot sunny days. Cuff the sleeves for that carefree vibe. Next, slip into a pair of distressed denim shorts to exude laid-back weekend style.

Ground the outfit with versatile knee-high brown suede cowboy boots. Their comfortable sole is perfect for lounging on blankets.

9. Brunch with the Girls

Brunch with the Girls
credit: instagram/angelbhathal

Get together with your best girlfriends for a boozy brunch in this playful coordinate. Begin with a pink and blue buffalo plaid shirt. Roll up the sleeves and wear it open like a lightweight jacket.

Next, cinch a pair of classic denim cutoffs with a bright pink leather belt for a pop of color.

Then finish with head-to-toe pink leather cowboy boots and handbag for a rich girl vibe. Add some dainty gold jewelry to complete this feminine meets cowboy look.

10. Date Night

Date Night
credit: instagram/soph.walsh

Instantly amp up those cutoffs for date night with the addition of a few key pieces. Start with a cropped black sleeveless top, which shows just a peek of skin. Make sure to pick one that hits right at your natural waist.

Next, throw on a black leather moto jacket, which brings casual edge to the romantic ensemble. Then pull the look together with dark brown leather cowboy boots, skinny through the shaft and slightly worn-in.

This downtown-chic meets Wild West outfit brings just the right vibe for a fun night out.

11. Shopping and Errands

Shopping and Errands
credit: instagram/mystyledlife

Running errands on the weekend is so much more fun when you feel cute!

Start with a light heather grey graphic tee, oversized for that laid-back look. Tuck it into a pair of high-waisted vibrant pink denim shorts. This playful pop of color screams fun weekend style.

Next pull the outfit together with classic black leather cowboy boots. Their comfortable sole makes them perfect for a full day of shopping and getting stuff done.

12. Day at the Fair

Day at the Fair
credit: instagram/luci.dcarpio

Can you smell the funnel cake yet? Hit up the state fair in style wearing this fresh take on classic pieces.

Begin with a black cropped sleeveless tee, which provides comfort on hot sunny days. Then slip into frayed hem denim cutoffs, a staple for any outdoor event.

Next layer on a breezy unlined orange bomber jacket, which embodies carefree summer spirit. Transition into knee-high white leather cowboy boots and matching white leather crossbody bag to pull the fun and festive outfit together.

13. Girls’ Night Out

Girls' Night Out
credit: instagram/bredoddsmith

Dancing the night away with your besties? Let this easy outfit take you from dinner to the dance floor and beyond.

Start with a flowy white blouse with a v-neckline. Look for a lightweight material like chiffon that flatters without clinging. Tuck it into sleek, high-waisted black denim shorts for timeless style. Next, slip into versatile knee-high black leather cowboy boots. Their walkable block heel is made for partying.

Finish with a black leather crossbody bag featuring bold gold chain straps. This effortlessly chic ensemble transitions seamlessly from cocktails to the club.

14. Beach Day

Beach Day
credit: instagram/brookemorosca

Soak up the summer sunshine in this breezy beach outfit. Begin with a light blue cropped tank top that hits right above the belly button. This is casual and comfortable, while still showing some skin.

Next, slip on a pair of frayed denim cutoffs. Make sure to roll the leg openings for a laid-back beach vibe. Then ground the look with sturdy brown leather cowboy boots that can handle sand and surf.

Their slight heel will keep you from sinking in the sand. Top it off with a wide-brim pink sunhat to complete this beachfront ensemble.

More Tips for Styling Cowboy Boots with Shorts

Beyond these 14 outfits, there are endless possibilities for pairing cowboy boots with shorts. Here are some additional tips and tricks to keep in mind:

  • Choose boots in neutral hues like black, brown, tan, or white. These provide versatility to pair with shorts in any color. Save bright shades like red for statement looks.
  • Consider shaft height based on leg length. Knee-high boots elongate petite frames. Ankle boots show off legs on taller women. Mid-calf can be flattering for many.
  • Watch heel height based on plans. Walkable block heels around 2 inches work for extended wear. Save taller heels for sitting occasions. Flatter heels provide comfort.
  • Select shorts in the right length. Aim for a 6-8 inch inseam or longer to balance taller cowboy boot shafts. Dramatic hem variations can look imbalanced.
  • Cuff wider-leg shorts to avoid bunching at the shaft. This creates a clean line and defined silhouette.
  • Size up on shorts to accommodate boot shafts fitting under the leg openings. Leave some breathing room.
  • Add tights or leggings if your shorts seem extra short with boots. Sheer black tights can add coverage while maintaining the look.
  • Dress shorts up or down with your top. Pair with feminine blouses for date night or graphic tees for casual cool.
  • Finish with statement accessories like oversized sunnies, straw hats, or stacked jewelry. Let these be the focus.

What’s your favorite way to wear cowboy boots with shorts?

Let us know in the comments below your tips, tricks, and favorite outfit ideas for rocking this trending style mashup!

Cowboy boots add an edgy twist to any shorts look. With so many options for tops, bottoms, boots, and accessories, the styling possibilities are endless.

We can’t wait to hear your thoughts on how to perfectly pair cowboy boots with shorts!

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