Cowboy boots with shorts is the one combination it took me a long time to warm up to. It always felt just a little too specific, costume-y, and well, stodgy.
Figuring out what to wear with the pairing was a big part of my hesitation too. There were so many old “rules” still bouncing around in my head. “Never wear boots in the summer.”
1. Plaid Shirt and Denim Shorts
I am so here for this lumberjack-inspired look that has a fun Western spin. You start with a plaid shirt that’s tied right at the front, which gives it this really cute cropped effect that shows a little skin.
A classic pair of denim shorts keeps the whole vibe super casual and easy.
Then you bring in a leather belt that perfectly matches the shirt. And to finish it all off? Some amazing knee-high cowboy boots that complement the outdoorsy feel.
I just love the play between masculine and feminine pieces here. You’ve got that menswear-style plaid shirt, but paired with shorts and those boots, it’s a total home run.
This is such a great look to try if you love mixing up different styles!
2. Cool & Casual
For those weekend errands or a super relaxed day date, you have to try this outfit. An oversized graphic tee is the key here, giving you that ultimate comfort we all crave.
Pair it with some light wash denim cutoffs to show off your legs. Then, it’s time to embrace your inner cowgirl with a pair of tall, black leather cowboy boots.
I love that the cowboy boots just pull the entire look together. It’s such a cool and casual vibe. You’ll stay comfy all day while making a seriously stylish statement!
3. Cool Cutoffs
You can beat that summer heat with some frayed denim cutoffs! A simple black cropped sleeveless top keeps things easy up top, letting the shorts be the main event.
The frayed hem on the denim cutoffs shows off your legs, and the knee-high white leather cowboy boots make them look even longer. A white leather crossbody is perfect for carrying your daily must-haves.
For those times when the weather is a little shaky, a bomber jacket is the perfect finishing touch.
4. Monochromatic Cowgirl
First up, we have this totally sleek, monochromatic outfit. A curve-hugging grey tube top gets paired with black shorts for a really streamlined silhouette.
For a little more coverage that still shows some skin, a black blazer is the perfect addition.
The metallic silver cowboy boots are the true showstoppers here, shining against the neutral palette. A small black crossbody with a chain-link strap completes that urban cowgirl vibe.
I’m obsessed with how the metallic boots make this monochrome look really pop! That contrast between the feminine shorts and the edgy boots is just so effortlessly cool.
5. Boho Babe
You can channel some serious flower child vibes with this bohemian chic outfit! A flowy white blouse made from a lightweight material feels so nice and breezy.
The distressed denim shorts are perfect for showing off your legs. And for that Western flair, just add a pair of knee-high brown suede cowboy boots.
This is hands down one of my favorite looks on the list! I’m so obsessed with how the flowy top and distressed shorts create a contrast with the rugged cowboy boots.
The whole laid-back boho vibe is just so cute for a summer music festival!
6. Denim Darling
Is there anything better for beating the summer heat than the ultimate warm-weather combo of denim and cowboy boots? A light blue cropped tank top keeps everything breezy.
Frayed denim cutoffs are perfect for showing off your legs. Then, you can kick things up a notch with a pair of brown leather cowboy boots.
To top it all off, a wide-brim pink sunhat is exactly what you need to keep that blazing sunshine away.
I love that the pink sunhat gives the perfect pop of color. This entire outfit just screams carefree summer fun!
7. Boho Cowgirl
Heading to a festival like Coachella or Austin City Limits this year? This boho-chic outfit will definitely make you stand out from the crowd.
Start with a breezy kimono-style cardigan that has colorful patterns and intricate designs. Layer it over a simple white spaghetti strap tank top and some high-waisted denim shorts.
This combo creates such a stylish desert-ready look that’s made for dancing all day long.
Next, slip into a pair of knee-high brown leather cowboy boots to really embody that effortless Indio style. And don’t forget a floppy sunhat and a hands-free crossbody bag to complete the laid-back festival vibe.
8. Playful in Pink
Time to inject some color into your cowgirl aesthetic with this vibrant pink outfit! A graphic tee with a fun print makes for a playful foundation. The high-waisted, vibrant pink denim shorts are perfect for showing off your stems.
To ground the whole look with a bit of ruggedness, add a pair of black leather cowboy boots.
This is another one of my absolute favorites! I’m obsessed with how the graphic tee contrasts with those girly pink shorts. And the cowboy boots just pull the whole outfit together flawlessly. It’s so fun and flirty!
9. Urban Cowgirl
This sleek, all-black outfit brings some serious urban edge to the cowgirl aesthetic. A ribbed tan tank is perfect for showing off glowing skin.
The high-waisted black leather shorts let you flaunt your curves in a way that’s edgier than classic denim.
A black leather belt cinches everything at the waist. To complete the rock n’ roll cowgirl look, add a pair of knee-high black leather cowboy boots. A patterned crossbody bag holds all your essentials and adds a great pop of color.
10. Sweet & Short
If you love to play up your feminine side, this outfit is definitely for you. A delicate white tank top with lace trim has such a romantic vibe.
When you pair it with frayed denim cutoffs, the ladylike top creates a perfect contrast with the rugged bottoms.
Some pretty pastel pink cowboy boots complement the soft color scheme so well. A dainty necklace is the perfect delicate accessory to finish off this flirty look.
The interplay between feminine and edgy is so fun here! I could totally see this outfit being perfect for a music festival or just a casual summer date.
11. Sexy in the City
Who ever said you can’t wear cowboy boots in the big city? This outfit brings a cool urban edge to the cowboy boot trend. A black blazer adds a sophisticated touch, worn open over a simple black bikini top to show a little skin.
Denim Bermuda shorts are great for flaunting your legs. A pair of over-the-knee dark brown leather cowboy boots totally emulates that popular over-the-knee boot trend while still keeping the Western flair.
To finish it off, a black leather handbag is perfect for carrying your essentials.
12. Dark Angel
It’s time to unleash your dark side with this all-black outfit. A flowy black blouse has this amazing ethereal quality. High-waisted black shorts are perfect for flaunting your curves.
The knee-high black leather cowboy boots provide a rugged edge. And a black leather crossbody bag with gold chain straps totally polishes off this rock n’ roll chic look.
You will love embracing your inner goth cowgirl in this dark angel outfit! I am obsessed with how the feminine, flowy blouse contrasts with the badass cowboy boots.
And that interplay between angelic and edgy all in black is so fun and unique!
13. Pretty in White
You can beat the heat in this breezy white look! A crisp white blazer gives it a polished touch. The flowy, mid-thigh shorts keep you cool while still showing some leg.
Then it’s time to embrace your inner cowgirl with a pair of brown leather cowboy boots.
I am such a fan of a good all-white outfit for summer! The cowboy boots give such a nice contrast against all the angelic white pieces. This outfit somehow manages to be both chic and totally down-to-earth at the same time.
14. Dangerous Curves
Va va voom! This sultry look shows some skin but still keeps a little bit of mystery. A black bikini top peeks out from underneath a sheer black blouse.
The blouse gives just a hint of coverage over the bikini while still letting your assets shine.
Frayed light denim cutoffs are perfect for flaunting those legs, while the over-the-knee brown leather cowboy boots make them look even longer.
A black leather crossbody bag carries all the essentials for this sexy summer outfit.
This is hands down one of my favorite looks on this list! I’m loving the interplay between the bikini top and that sheer blouse.
And those over-the-knee cowboy boots are so hot. This is definitely an outfit for a steamy summer night out!
More Tips for Styling Cowboy Boots with Shorts
Beyond these outfits, there are endless ways to pair cowboy boots with shorts. Here are a few more tips and tricks I always keep in mind:
- I always say to start with boots in neutral hues like black, brown, tan, or even a crisp white. They provide so much versatility and pair well with shorts in pretty much any color. You can save brighter shades like red for those statement looks.
- Think about the shaft height based on your leg length. I find that knee-high boots can really elongate a petite frame. Ankle boots are great for showing off your legs if you’re taller. And mid-calf boots are usually flattering on everyone.
- Pay attention to the heel height depending on your plans for the day. A walkable block heel around 2 inches is perfect for all-day wear. You’ll want to save any taller heels for occasions where you’ll be sitting more. Of course, flatter heels are always a win for comfort.
- Select shorts with the right length. My advice is to aim for a 6 to 8-inch inseam or even longer to balance out the taller cowboy boot shafts. Sometimes dramatic hem variations can look a little imbalanced.
- It’s a good idea to cuff wider-leg shorts so they don’t bunch up at the boot shaft. This simple trick creates a really clean line and a more defined silhouette.
- Consider sizing up in your shorts to make sure the boot shafts can fit comfortably under the leg openings. You definitely want to leave a little breathing room.
- Add tights or leggings if you feel like your shorts are extra short with your boots. A pair of sheer black tights can give you a little more coverage while still keeping the look.
- You can dress your shorts up or down just by changing your top. Try pairing them with a feminine blouse for a date night or a cool graphic tee for a more casual vibe.
- Don’t forget to finish your look with statement accessories. I love adding things like oversized sunnies, a straw hat, or some stacked jewelry. Let those pieces be the focus!
