Cheeky Denim Shorts
Cheeky denim shorts are your go-to for turning heads and catching rays, all while keeping that effortlessly cool vibe. Whether you're strutting down the boardwalk or dancing under the stars, these shorts have your back like your bestie at a summer festival. With a playful edge and a dash of sass, cheeky denim shorts are here to make sure you own every moment with confidence and flair. Slip into these wardrobe staples and let your fearless side shine through—because life's too short for anything less than fabulous!
$19.90
A pair of black sheer lace shorts with a built-in panty lining for cheeky coverage.
$54.90
A pair of medium denim high-rise shorts adorned with rhinestone chains and trendy distressed accents.
$29.90
A sleek pair of black faux leather high-rise shorts with a fitted cheeky hem and side pockets.
$29.90
A chic pair of black tiered lace shorts with a cheeky fit and stretchy knit fabric.
$19.90
A pair of black faux leather hot shorts with a mid-rise waist and cheeky fit.
$34.90
A pair of leopard print hot shorts with sequin embroidery and a cheeky, high-rise fit.
$34.90
A pair of ivory knit shorts with a cheeky fit and tiered ruffled design for festivals.
$19.90
A pair of black ponte micro shorts with a high-rise waist and form-hugging silhouette.
$39.90
A sleek pair of black faux leather hot shorts with a mid-rise waist and cheeky hem.
$29.90
A chic pair of red gingham ruffle shorts with a low-rise waist and cheeky bottom.
$36.90
A pair of black knit hot shorts with square rhinestone accents and a cheeky fit.
$24.90
A pair of snake print, low-rise knit shorts with a form-hugging, cheeky fit for festivals.
$34.90
A stylish pair of dark denim shorts featuring a mid-rise waist and trendy lace-up front.
$36.90
A pair of mid-rise denim hot shorts with a color wash tint and cheeky fit.
$32.90
A pair of high-rise dark denim shorts with a form-hugging fit and stretch fabric.
$34.90
A trendy dark denim mini skort with a mid-rise waist and bodycon fit, featuring a skirt overlay.
$26.90
A sassy leopard-print faux suede short with a high-rise waist and cheeky fit in brown.
$36.90
A medium denim high-rise skort featuring a ruffled mini skirt overlay and form-hugging fit.
$32.90
A pair of white mid-rise denim shorts with distressed accents and a form-hugging fit.
$29.90
A dazzling pair of black hot shorts featuring rhinestone embellishments and a stretchy cotton-blend fabric.
$34.90
A pair of olive mid-rise denim shorts with a trendy lace-up side design for festival flair.
$36.90
A laidback pair of medium denim jorts featuring a relaxed silhouette and knee-length hem.
$32.90
A trendy black denim mini skort with a ruched side seam and adjustable drawstring.
$28.90
A pair of brown lace hot shorts featuring frilly ruffles and a cheeky fit.
$39.90
A pair of faux leather red hot shorts with a low-rise waist and form-hugging fit.
$34.90
A dark denim mini skort featuring a mid-rise waist and a stylish front skirt overlay with slit.
$32.90
A trendy pair of grey acid wash denim shorts with a mid-rise waist and form-hugging fit.
$16.90
A pair of white cherry print pajama shorts in soft ribbed knit with a low-rise waistband.
$22.90
A pair of pink low-rise ribbed knit pajama shorts offering a cheeky, fitted silhouette.
$34.90
A high-rise grey acid wash denim skort with an envelope front design and form-hugging fit.
$32.90
A pair of dark denim high-rise shorts with a form-hugging fit and four-pocket styling.
$9.97 $19.90 50% off
A cozy pink chenille knit lounge short with a mid-rise waist and cheeky fit.
$16.90
A playful pair of pink knit pajama shorts featuring a zesty orange print and cheeky fit.
$39.90
A medium denim skort featuring a pleated mini skirt overlay and edgy exposed pockets.
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Oh-so-contemporary and sleek, these smooth faux leather shorts feature a high-rise waist, front snap-button, hidden zipper closure, side pockets, seam detailing, and a fitted cheeky hem. The lined faux leather fabric has minimal stretch. Complete the look in a basic tee and boots for an edgy vibe. Fit & FeaturesHigh-rise waist, Front snap-button and hidden zipper closure, Side pockets, Seam detailing, Fitted, cheeky hem, Faux leather lined fabric, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Smooth Moves PU High-Rise Shorts in Black | Size: L | Leather
Create your own fairytale this Halloween with hot shorts that feature a chic tiered lace design and a cheeky fit. Perfect for creating a masquerade-inspired costume or classic icons. Complete costume with the matching mask or plaid top. Fit & FeaturesStretchy knit fabric with tiered floral mesh design, Mid-rise elasticized waist, Cheeky bottom coverage, Form-hugging fit, Shorts in size small have an 8.5" front rise with a 2" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Fairytale Tiered Lace Hot Shorts in Ivory | Size: S | Knit Fabric/Mesh Fabric
Short, sweet, and exceptionally poised! These high-rise denim shorts are everything for elevating your style. Pair with the matching vest. Shop Matching Vest: Exceptional Poise Sleeveless Button Denim VestFit & FeaturesDark wash denim fabric with stretch, High-rise waist, Front button and hidden zipper closure, Form-hugging fit, Short-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Exceptional Poise High Rise Denim Shorts in Dark Denim | Size: S
Style up your Halloween costumes with these sleek faux leather hot shorts featuring a mid-rise waist and a cheeky form-hugging fit. Dress up as a champion racer with the checkered bustier and cropped jacket, or as a sporty babe with the jersey tee and football rhinestone clutch. Fit & FeaturesStretchy faux leather fabric, Mid-rise elasticized waist, Cheeky form-hugging fit, Shorts in size small have a 9" front rise with a 1.5" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Vibe Faux Leather Hot Shorts in Black | Size: L | Leather/Rhinestone
Turn up the shine in these groovy metallic faux leather shorts perfect for themed parties! With a high-rise waist and form-hugging fit, these shorts accentuate your curves while providing a flattering silhouette. The cargo flap pockets offer functionality while the front button and hidden zipper closure secure the style. Complete the look in a mesh long sleeve top and heels! Fit & FeaturesCoated metallic faux leather fabric, slight stretch, High-rise waist, Form-hugging fit, Front button and hidden zipper closure, Three waist pockets, lower cargo flap pockets, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Turn Up Cargo Metallic Faux Leather Shorts in Black | Size: L
Put on a show arriving in these rhinestone denim shorts! They feature a flattering high-rise waist, and stunning rhinestone swag chains across the front for a touch of glamour. The distressed accents add a trendy edge, while the fitted hem ensures a perfect fit. Complete the look in a bodysuit and boots for a concert or music festival! Fit & FeaturesHigh-rise waist, Rhinestone swag chains across the front, Distressed accents, fitted hem, Front button and hidden zipper closure, Five-pocket styling, belt loop accents, Medium wash denim fabric, no stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Pop Star Rhinestone High-Rise Denim Shorts in Med Denim | Size: L
Grab your besties and make plans to rock these mid-rise denim shorts for fun under the sun! The mid-rise waist and form-hugging fit flatter your curves, while the distressed accents and cut-off hem add a touch of edge. Complete the look in a cute bodysuit and platform sneakers! Fit & FeaturesDenim fabric, minimal stretch, Mid-rise waist, Distressed accents, cut-off hem, Form-hugging, Front button and hidden zipper closure, five-pockets, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sunny State Mid-Rise Distressed Denim Shorts in White | Size: S
Create a sassy and chic night out look with these hot shorts designed with leopard-printed faux suede fabric. They feature a high-rise waist and a cheeky form-hugging fit. Style with a crop top and boots! Fit & FeaturesLeopard printed faux suede fabric, High-rise waist, Cheeky form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sassy Chic Leopard Print Faux Suede Hot Shorts in Brown | Size: M
Create a sassy look for your next night out in these leopard print hot shorts featuring a high-rise waist and a cheeky form-hugging fit. The all-over sequin embroidery adds a cool glam vibe to the sultry style. Fit & FeaturesLeopard print woven fabric with knit lining, plenty of stretch, All-over clear sequin embroidery, High-rise waist, Side zipper with hook-eye closure, Cheeky form-hugging fit, Shorts in size small have an 11" front rise with a 1" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sassy Look Sequin Leopard Print Hot Shorts | Size: S | Knit Fabric/Woven Fabric
Windsor Time To Celebrate Sequin Hot Shorts in Silver
$15.97 $36.90
57% off
Flaunt your sparkle in these sequin hot shorts! With a cheeky fit and mid-rise elastic waist, these shorts bring the party vibes. Perfect for dancing the night away! Fit & FeaturesSequin embellished sheer knit fabric, knit lining, moderate stretch, Mid-rise elasticized waist, Cheeky fit bottom, Shorts in size small have a 10" front rise with a 1.5" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Time To Celebrate Sequin Hot Shorts in Silver | Size: L | Knit Fabric
Cheeky Denim Shorts
Cheeky denim shorts are basically the ride-or-die of your wardrobe—always down for a little adventure, never judging your last-minute plans, and ready to turn even a coffee run into a main character moment. Whether you’re running errands, hitting up a last-minute road trip, or just living for that spontaneous rooftop hang, these shorts are your go-to for showing off a little leg and a lot of attitude. There’s something about slipping into a pair of cheeky jean shorts that just hits different—maybe it’s the way they hug your curves in all the right places, or the fact that they make you feel like you can take on anything (including that group text drama). High rise cheeky denim shorts are a total confidence boost, cinching your waist and giving you that long-legged, “I woke up like this” energy that turns sidewalks into runways. And let’s be honest, cheeky black shorts are a whole vibe on their own—edgy, versatile, and perfect for those nights when you want to serve a little mystery with your mischief.
When you’re shopping for cheeky shorts denim, it’s all about finding that perfect fit that feels like it was made just for you. Look for details like raw hems, distressed accents, or a little bit of stretch—these touches don’t just add personality, they make every move feel effortless. If you’re gifting a pair (major bestie points, by the way), think about the recipient’s style: are they the life of the party, always down for a festival or a weekend escape? Or maybe they’re more about those laid-back brunches and chill afternoons. Either way, cheeky denim shorts are a foolproof pick for birthdays, bachelorette weekends, or just because you want to remind your favorite person that she’s the moment. Pair them with a crop top and chunky sneakers for a look that screams “catch me if you can,” or throw on a slouchy tee and sandals for those easy, breezy days when you’re just feeling yourself.
No matter how you style them, cheeky denim shorts are the ultimate flex for showing off your playful side and making every outfit a little more unforgettable. Whether you’re dancing under the sun, catching up with your crew, or just vibing solo, these shorts have your back (and your best angles). If you’re ready to level up your collection with the latest must-haves, check out our full lineup of Cute Shorts and get ready to serve looks all day, every day.