Cheeky Swim Bottoms

Ready to turn heads and break a few hearts? Cheeky swim bottoms are your ticket to main character energy—whether you’re poolside posing, dancing in the sand, or making your own splashy entrance. These flirty fits were made for the fearless, the fun-loving, and the girls who know every sun-soaked moment deserves a little extra attention. Slip into cheeky swim bottoms and get ready to serve looks, soak up compliments, and own every wave of confidence that comes your way.

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Windsor Snake Em Down Low-Rise Hot Shorts

$24.90

A pair of snake print low-rise hot shorts in stretchy knit fabric for stylish festival looks.

Windsor Good At Being Bad Lace Hot Shorts in Brown

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Windsor Good At Being Bad Lace Hot Shorts in Brown

$11.97 $28.90 59% off

A pair of brown lace hot shorts featuring frilly ruffles and a cheeky fit.

Best Look High-Rise Shaper Thong in Black

$24.90

A black high-rise shaper thong in scuba knit fabric offers smoothing support and comfort.

Windsor Stand Out Mid-Rise Denim Hot Shorts

$36.90

A stylish pair of mid-rise denim hot shorts with a color wash tint and cheeky fit.

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Windsor Sealed With Charm Short A-Line Dress in White-2

$9.97 $38.90
74% off

(34)

Seal your look with this charming A-line dress for a rehearsal dinner or sunset dinner date! The dress features a sleeveless sweetheart neckline, adjustable spaghetti straps, a padded bust, and a flattering short-length hem. Complete the look in chic block heels. Fit & FeaturesSleeveless sweetheart neckline, Adjustable spaghetti straps, Padded bust, A-line silhouette, Short-length hem, Poplin fabric, stretchy knit lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sealed With Charm Short A-Line Dress in White-2 | Size: L | Knit Fabric

Windsor Smooth Moves PU High-Rise Shorts in Black

$29.90

(32)

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: M | Leather

Windsor Chic Fairytale Tiered Lace Hot Shorts in Ivory

$29.90

(27)

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: M | Knit Fabric/Mesh Fabric

Windsor Center Stage Rhinestone Hot Shorts in Black-2

$29.90

(11)

Take the stage in this rhinestone hot shorts and heat the scene! Fit & FeaturesRhinestone embellishments, Stretchy cotton-blend knit fabric, Low-rise waist, Fitted silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Center Stage Rhinestone Hot Shorts in Black-2 | Size: XS | Cotton/Knit Fabric/Rhinestone

Exceptional Poise High Rise Denim Shorts in Dark Denim

$36.90

(9)

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: M

One And Only Mid-Rise Hot Shorts in Black

$24.90

(5)

Elevate your style with these hot shorts for any fun plans! These mid-rise shorts provide a comfortable fit and accentuate your curves in a sleek, form-hugging fit. Fit & FeaturesWoven fabric, Mid-Rise waist, Back zipper closure, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor One And Only Mid-Rise Hot Shorts in Black | Size: XS | Woven Fabric

Olessa Short Sleeve A-Line Slit Satin Formal Dress in Navy Blue

$59.90

(4)

The silky satin and curve-flattering silhouette make the Olessa formal dress feel so special! The dress boasts adorable flutter short sleeves and a chic A-line silhouette with a high front slit for effortless movement. Fit & FeaturesPremium satin fabric, woven lining, Short flutter sleeves, V-neckline, padded bra cups, Back zipper and hook-eye closure, High front slit, A-line silhouette, floor-length hem, Runs true to size, Where to Wear:Prom, weddings, bridesmaids, galas, black tie parties, engagement parties, rehearsal dinner, fancy date nights, big milestone celebrations Free Shipping on All Orders Over $75. | Windsor Olessa Short Sleeve A-Line Slit Satin Formal Dress in Navy Blue | Size: S | Satin Fabric

Summer Spice Low-Rise Ruffle Hot Shorts in Black

$29.90

(3)

Set the tone in this spicy ruffled hot short with a flattering low-rise waist that flaunts your figure! Pair with the matching top to complete the vibe. Fit & FeaturesMesh-lined fabric, Low-rise waist, Ruffled, fitted silhouette, Runs true to size, Shop The Matching Top: Summer Spice Lace-Up Ruffle Crop Top Free Shipping on All Orders Over $75. | Windsor Summer Spice Low-Rise Ruffle Hot Shorts in Black | Size: M

She's A Wild One Leopard Ruffle Hot Shorts

$29.90

(3)

Shake it up in this leopard ruffle hot short for a night on the prowl! Shop Matching Top: She's A Wild One Leopard Ruffle Tube TopFit & FeaturesLeopard print, mesh fabric, stretchy knit lining, High-rise waist, Ruffled silhouette, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor She's A Wild One Leopard Ruffle Hot Shorts | Size: L | Knit Fabric/Mesh Fabric/Mesh Fabric

Windsor Maybe Tonight Leopard Ruffle Shorts

$29.90

(3)

Bring the fierceness to the night in these leopard shorts made for dancing all concerts or the bar! With a flattering high-rise waist and ruffled hem, these shorts are perfect for stepping up your style. Fit & FeaturesLeopard print, stretchy knit fabric, High-rise waist, Ruffled short hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Maybe Tonight Leopard Ruffle Shorts | Size: M | Knit Fabric

Cheeky Swim Bottoms

Cheeky swim bottoms are the ultimate way to dial up the confidence and show off your playful side, no matter the season. Whether you’re squeezing in one last pool day before the weather turns or you’re booking a spontaneous getaway to chase the sun, these barely-there beauties are all about celebrating your shape and making every swim a statement. There’s something undeniably empowering about slipping into a pair of cheeky bottoms—the kind that sits just right, hugs your curves, and makes you feel like the main character in your own beachy daydream. Picture this: salt in your hair, a sun-warmed towel under you, and the perfect fit that lets you move, lounge, and snap a million photos without a second thought. Cheeky styles aren’t just for the bold or the beach regulars—they’re for anyone who wants to break out of the basic bikini rut and try something a little more unexpected. They’re the kind of piece that turns a routine swim into a mood, whether you’re catching up with friends at a rooftop pool, sneaking in a hot tub session after dark, or just soaking up some vitamin D in your backyard. And if you’re the friend who always brings the fun gift to a bachelorette or birthday bash, a set of cheeky swim bottoms is a guaranteed hit—equal parts practical and playful, and always ready for a spontaneous adventure.

When you’re picking out your next pair, it’s all about the details. The right cheeky bottom balances coverage and reveal, giving you that just-enough confidence boost without feeling overexposed. Look for adjustable ties or ruched seams if you want to customize your fit, or opt for seamless edges for a smooth, second-skin feel that won’t dig in when you’re lounging or diving in. Fabric matters, too—quick-dry blends and double lining keep everything secure (and selfie-ready), while bold prints, textured fabrics, or metallic finishes let you channel whatever vibe you’re feeling that day. Don’t be afraid to mix and match—cheeky bottoms are practically made for pairing with your favorite oversized button-downs, breezy cover-ups, or that one sun hat you never leave home without. And if you’re building a swim drawer that can handle every mood, occasion, and last-minute invite, you’ll want to check out our selection of Cute Bikini Tops to create your own perfectly mismatched (or totally coordinated) set.

Cheeky swim bottoms aren’t just a trend—they’re a mindset. They’re for the days when you want to show up and own your style, whether you’re poolside in October (yes, heated pools count) or plotting your next warm-weather escape. They’re the perfect pick for the friend who’s always down for a spontaneous dip, the sister who claims she “doesn’t do swimwear” until she tries on a pair and instantly gets it, or anyone who’s ready to retire the safe, standard-issue black bottoms for something with a little more personality. Even as the temps cool down, there’s something about pulling on a cheeky bottom that feels like a mini rebellion against the ordinary—a reminder that you don’t need a reason (or a season) to wear what makes you feel amazing. Whether you’re gifting a set to your vacation-obsessed bestie or treating yourself to a little swimwear refresh, these styles are designed to make every pool day, hot tub night, and sun-drenched getaway feel like an event. Because at the end of the day, it’s not just about what you wear—it’s about how you feel in it, and cheeky swim bottoms are here to make sure that feeling is nothing short of unforgettable.

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Cheeky Swim Bottoms

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