Dress to Wear With Cowgirl Boots: Best 14 Outfit Ideas

There is just something about the rugged yet chic vibe of cowgirl boots that makes any outfit instant cooler. Maybe it is the western flair or the unstate confidence they exude. As a self proclaimed cowgirl boot fanatic. I have spent many mornings staring at my closet, wondering what the perfect pairing would be for those beloved knee high kicks.

Well, wonder no more! Whether you’re a tried and true country gal or just appreciating that buckaroo vibe. This guide showcases 14 fashion forward ways to rock cowgirl boots from day to night. Get ready to turn heads with these effortlessly stylish looks!

1. Classic Denim

If you want an effort, time less look, denim is your friend with cowgirl boots. There is just something about the combo of rugged denim and western boots that screams cool girl.

Skinny Jeans Tucked In

Skinny Jeans Tucked In

The most obvious denim pairing is a great pair of body hugging skinny jeans tucked right into those boots. Keep it simple with a white tee and chunky sweater on top. Or rock it with an oversize plaid or denim shirt tied at the waist for a more put together vibe.

Denim Overall Dress

For a youthful, low key look, an oversized denim overall dress or jumper looks amazing with cowgirl boots peeking out underneath. Throw on a graphic tee or crop top to give it some shape. This is such an easy, grab and go outfit for weekends or festivals.

Chambray Shirt Dress

If you want to elevate the typical jeans and a tee, a chambray shirt dress is so versatile. Keep it casual by just belting the waist. Dress it up with some statement jewelry and a moto jacket for date night. No matter how you style it the cowgirl boots give it an extra kick of cool.

2. Dresses & Skirts

Who says cowgirl boots only pair perfectly with denim and plaid. They also look amazing with dresses and skirts for a fun mix of femininity and western edge.

Dresses & Skirts

Floral Midi Dress

A breezy, feminine floral print midi dress gets totally revamped with the addition of some cowgirl boots. Toughen up the romantic vibe by add a jean jacket on top. This is such a cute look for weekends and outdoor concerts.

Denim Mini Skirt

Another great denim option is a denim mini skirt paired with an off the shoulder boho top. The short skirt shows off those tall boots for an updated take on western inspired fashion.

Eyelet Lace Dress

A super flirty, women look, an adorable white eyelet lace mini dress looks so sweet with cowgirl boots and maybe even a cowgirl hat. This outfit is ideal for outdoor weddings or backyard parties when you want to feel extra whimsical.

3. Elevated Casual Looks

You can definitely dress up those cowgirl boots, but they also add a cool, casual vibe to everyday basics. These looks are perfect for brunch with friends or just running errands in style.

Elevated Casual Looks

Kimono Top & Skinnies

Take your skinny pants from boring to boho by pairing them with a flowy, patter kimono top and cowgirl boots. The loose, draped vibe contrasts so nicely with the structured boots.

T-Shirt Dress

A basic t-shirt dress gets an edgy revamp when you add cowgirl boots and maybe a jean jacket or vest over top. 

Culotte Jumpsuit

For a sleek yet comfy look, try a culotte jumpsuit with the wide leg cropped bottoms hitting right at the top of your boots. Add a belt to define your waistline.

4. Layered Looks for Cool Weather

Don’t let chilly temps stop you from rocking cowgirl boots.Layering pieces like jackets, sweaters, and tights allows you to keep those boots as the star of the show.

Sweater Dress Over Skinnies

For a cozy but cute fall or winter look, try a sweater dress over your skin with the boots peeking out on the bottom. Add pops of color like a plaid blanket scarf for extra warmth.

Sweater Dress Over Skinnies

Floral Skirt with Tights

A pretty floral skirt looks so charming when worn with cozy knit tights and tall cowgirl boots. Layer on a jean jacket or blazer on top to pull the outfit together.

Faux Fur Vest Layered Outfit

Make a serious statement by rocking a faux fur vest over a printed dress or skirt, belted at the waist, and with cowgirl boots grounding the look. Such a fun and glamorous cold weather combo!

5. Glam Night Out Looks

Cowgirl boots instantly add personality and flirty flair to dressier ensembles, making them ideal for date nights and girls nights out.

Leather Leggings

For a sleek, sassy vibe, pair leather leggings with a loose, flowy blouse or tunic untucked over top. The cowgirl boots give this all black outfit a fun, unexpected twist.

Slip Dress Over Turtleneck

Slip Dress Over Turtleneck

A slinky slip dress layered over a fitted turtle neck and completed with those cowgirl boots. Such an easy but impactful look.

Sequin Mini Skirt

For maximum shimmer and glam, go all out with a sequin mini skirt. Pair it with a strappy camisole, oversized blazer or faux fur jacket, and of course, fabulous cowgirl boots.

6. Flowy Florals & Cowboy Chic

Flowy floral dresses and tops bring an airy, ethereal vibe that perfectly contrasts with the rugged look of cowgirl boots. Opt for breezy fabrics like chiffon or crepe in pretty ditsy floral prints or bold blooms. 

6. Flowy Florals & Cowboy Chic

A floaty floral midi dress looks absolutely dream paired with scuffed cowboy boots for a boho prairie princess aesthetic. Or try a romantic floral peasant top tucked into cutoff denim shorts with cowgirl boots for an ultra cool cowgirl meets coachella outfit. 

The flowing femininity of floral patterns gets totally grounded and toughened up by those iconic western boots. It’s the ideal combo of delicate and rugged, pretty and gritty. 

7. Swirls Meet Western Whirls

For a funky, retro inspired look, pair bold swirling paisley or psychedelic prints with edgy cowgirl boots. Think flowy paisley dresses, swirling printed blouses, or psychedelic wide leg pants. The whimsical, groovy vibes of these swirling patterns get completely grounded by no nonsense western boots. 

7. Swirls Meet Western Whirls

It’s the perfect marriage of 70s bohemian flair with frontier attitude. A paisley print maxi dress stays breezy and chic when anchored by chunky cowboy boots. Or do an ultra cool paisley button down shirt tucked into flared corduroy pants with your favorite scuffed boots. 

The cowboy boots bring an earthy, rugged touch to these trippy, kaleidoscopic prints. Play with clashing the flowy, free spirited patterns against the utilitarian structure of the boots. It’s an unexpected mix of retro psychedelic fashion with ranch-hand roots for a look that’s equal parts far-out and down to earth.

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8. Peplum Perfection with a Western Kick

  • Structured peplum tops flare femininely. 
  • Edgy cowboy boots stomp with attitude. 
  • The soft girly shape meets rugged charm.
  •  A chic contradiction in one look.

9. Red Blooms and Silver Boots

9. Red Blooms and Silver Boots
  • Vivid red floral patterns flourish boldly. 
  • The bright blooms exude vivacious energy. 
  • Shimmering silver cowboy boots add a sleek edge. 
  • Fiery florals meet cold metal for cool contrast.

10. Polka Dots & Cowboy Thoughts

Polka dots instant add a fun, flirty vibe to any outfit. But when you pair those playful spotted prints with rugged cowboy boots, you get an unexpected mix of girly and edgy. A polka dot dress or blouse feels infinitely cooler when grounded by distressed leather boots. 

10. Polka Dots & Cowboy Thoughts

The juxta position of the sweet, dainty pattern against the utilitarian work boot creates a look that exudes both female and toughness. Try a polka dot skater skirt with a plain tee tucked in and cowboy boots for a cute yet confident day time style. 

A silky polka dot cami and studded boots for a chic night out ensemble. The key is letting the kicks be the rugged anchor to the whimsical, quirky polka dots. It is a fun pattern clash that feels simultaneously retro and modern.

11. Rustic Ruffles

Delicate ruffles bring a romantic, prairie inspired feel that gets totally toughened up when paired with rugged cowgirl boots. A ruffled blouse or dress looks sweetly demure until you add some scuffed leather cowboy kicks into the mix. 

11. Rustic Ruffles

Suddenly the vibe goes from precious to edgy cowgirl chic. Try a ruffled swiss dot midi dress belted at the waist with your favorite turquoise jewelry and kicks for a modern take on country western style. 

Tuck a ruffled boho top into cutoff jean shorts and pull on your boots for an ultra cool ranch hand aesthetic. The key is finding pieces with soft ruffled tiers or fluttering sleeves to contrast with the rugged structure of the boots. It’s where a delicate prairie girl meets a brave frontier explorer. Plays on proportion keep this ruffled western look fun and fresh.

12. Boho Western Elegance

That exudes laidback sophistication with rustic charm, combining bohemian pieces with cowboy boot attitude. Start with a flowy printed maxi dress or tiered skirt in an eclectic global pattern like paisley, aztec, or batik. Toughen it up by adding weathered cowboy boots that lend an earthy, well-traveled vibe. 

12. Boho Western Elegance

The mix of exotic prints with basic ranch hand boots creates this unexpectedly elegant yet totally chill aesthetic. A crinkly printed blouse tucked into distressed boyfriend jeans with cowgirl boots is the epitome of cool boho girl gone a little western. Pile on lots of layered necklaces, concho belts, turquoise cuffs.

Those native american and southwestern inspired jewelry pieces amplify the vibe. It’s a refined yet free-spirited style that walks the line between vintage bohemian and modern cowgirl. The boots keep it grounded while the flowing prints and patterns let you wander.

13. Polka Dots & Cowboy Boots

Polka dots feel instantly playful and feminine, while cowboy boots exude a rugged, no nonsense attitude. Combining these two contrasting vibes creates an unexpectedly cool look with lots of personality. Try a polka dot dress or blouse with your favorite distressed leather cowboy boots.

13. Polka Dots & Cowboy Boots

The juxta position of the sweet, whimsical print with the tough workwear boots makes for a fun pattern play. A polka dot skater skirt with a tucked tee and cowboy boots is a cute yet edgy daytime style. Or go for max contrast with a silky polka dot camisole and studded boots for a chic night out ensemble. The key is letting the cowboy kicks anchor the playful, retro polka dot pieces. 

It’s an easy way to merge girly with edgy for an outfit that feels modern but still feminine. Lean into the vintage vibe by choosing a classic polka dot piece in a fitted cut to complement the heritage cowboy boots.

14. Denim & Blooms

There’s something so perfectly effortless and chic about pairing denim with floral prints while rocking a pair of cowgirl boots. The casual, lived-in vibe of denim gets an ultra-feminine twist with breezy, blooming florals.Then the cowboy boots come in and add that perfectly rugged, ranch-hand finish. 

14. Denim & Blooms

A floral print prairie dress with a denim jacket shrug and cowboy boots is such an ideal combination for spring and summer. The boots keep the pretty dress grounded while the denim gives it an edge. For a more tomboy take, rock a floral blouse or camisole tucked into cut-off denim shorts with your favorite scuffed white cowboy boots. 

The blooming patterns against the denim blues creates this cool vintage, countryside cowgirl aesthetic. Play with proportion by choosing an oversized floral print that contrasts with tight denim bottoms or vice versa. It’s the perfect way to blend romantic prairie vibes with cowboy tough girl flair.

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Dresses to wear with cowboy boots for a wedding

The perfect dress to pair with cowboy boots for a wedding can add a touch of rustic charm to your ensemble. Opt for a flowing, bohemian style dress with delicate lace details for a whimsical feel. 

Dresses to wear with cowboy boots for a wedding

A floral print sundress can evoke a relaxed, country vibe that complements the ruggedness of cowboy boots. Keep accessories minimal to let the boots and dress steal the show. It creates a look that’s both chic and effort stylish for any wedding celebration.

Accessorize Your Cowgirl Boot Outfits

No matter which cowgirl boot outfit you choose, have fun accessories to really make it your own unique look:

Accessorize Your Cowgirl Boot Outfits
  • Bags: Crossbody bags, totes, backpacks, belt bags, all look amazing with cowgirl boots.
  • Jewelry: Layer on chunky turquoise rings, concho belts, stamped metal cuffs and pendants.
  • Hair: Braid a few face framing pieces, rock a high pony, or top it off with a fedora and cowgirl hat.
  • Extras: Tie on a printed scarf, add flair with fringe, or pile on delicate necklaces.

Styling Tips for Cowgirl Boots

Styling Tips for Cowgirl Boots

To really nail these looks, keep these tips in mind when styling with cowgirl boots:

Break them in first:Wear thick socks and walk around to make stiff new boots more comfortable before taking them out.

Consider height:Avoid super short dresses skirts with taller boot shafts for a more flattering look.

Have fun mixing: Don’t be afraid to mix different patterns, textures, and styles for a more unique aesthetic.

Tuck smartly:Tuck skinny jeans pants into boots smoothly or scrunch them slightly above the shaft.

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Conclusion

From vintage western vibes to modern city sleek, the versatile charm of cowgirl boots allows them to be styled in so many fashionable ways. Whether dressing them up with flirty dresses and skirts or keeping it casual chic with denim. The key is finding that perfect blend of tough and feminine that these iconic boots exude.

So grab your favorite pair of knee highs and don’t be afraid to get a little wild. With the 14 outfit ideas here, you will be sure to turn heads and stay supremely stylin from day to night adventures. 

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