Date Night Shorts
Get ready to turn heads and break hearts with our sizzling collection of date night shorts! Whether you're planning a romantic dinner under the stars or dancing the night away, these shorts are your ticket to unforgettable nights and endless compliments. From flirty hems to bold prints, each pair is designed to make sure you're the star of the show. So slip into your favorite pair, add a dash of confidence, and let those date night shorts do all the talking while you steal the spotlight!
$29.90
A sleek pair of black faux leather high-rise shorts with side pockets and a cheeky hem.
$54.90
A glamorous pair of medium denim shorts featuring rhinestone chains and a flattering high-rise waist.
$34.90
A sassy leopard print short with high-rise waist and sequin embroidery for a glamorous night out.
$34.90
A pair of ivory knit shorts with a cheeky fit and tiered ruffles, perfect for festivals.
$29.90
A leopard print ruffle short with a high-rise waist and form-hugging fit.
$36.90
A pair of black knit hot shorts with square rhinestone accents and a cheeky fit.
$12.97 $30.90 58% off
A trendy pair of camel faux suede shorts featuring a stylish lace-up front and back zipper closure.
$39.90
A dazzling pair of black sequin hot shorts perfect for making a statement on the dancefloor.
$27.90
A black ponte mini skort with a high-rise waist and dual front slits for a chic look.
$24.90
An ivory mini skort with airy sheer floral lace, ruched high waist, and asymmetric hanky hem.
$29.90
A chic pair of red hot shorts featuring a tiered lace design and form-hugging fit.
$34.90
A trendy dark denim mini skort with a mid-rise waist and bodycon fit, featuring a skirt overlay.
$32.90
A pair of high-rise dark denim shorts with a form-hugging fit and stretch fabric.
$22.90
A sleek black bodycon mini skort with faux leather fabric and a high-rise waist.
$26.90
A groovy pair of black metallic faux leather shorts with a high-rise waist and cargo pockets.
$29.90
A black ponte mini skort with rhinestone bows, high-rise waist, and flirty front slit.
$36.90
A medium denim skort with a dual slit overlay and form-hugging fit for chic styling.
$26.90
A black knit mini skort with a high-rise waist and romantic lace trim hem.
$22.90
A chic black satin mini skort featuring a high-rise waist and adjustable ruched side seam.
$36.90
A medium denim high-rise skort featuring a ruffled mini skirt overlay and form-hugging fit.
$9.97 $39.90 75% off
A dark denim mid-rise skort with pleated silhouette and woven shorts lining for comfort.
$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.
$19.90
A pair of black ponte micro shorts with a high-rise waist and form-hugging silhouette.
$34.90
A denim mini skort with a mid-rise adjustable belted waist and form-hugging silhouette.
$9.97 $29.90 67% off
A chic black romper featuring a sleeveless square neckline, pleated skirt overlay, and mini bow accent.
$9.97 $32.90 70% off
A mustard corduroy mini skort with a high-rise waist and faux wrap-front design.
$34.90
A dark denim high-rise skort with a faux wrap-front and fitted shorts for a trendy casual look.
$29.90
A flirty black lace mini skort with tiered ruffles and fitted shorts for a cute look.
$42.90
A pair of faux leather brown hot shorts with fringed sides and a form-hugging fit.
$19.90
A pair of black sheer lace shorts with a built-in panty lining for cheeky coverage.
$15.97 $36.90 57% off
A mid-rise off-white denim skort with ruffled lace trim and a flattering bodycon fit.
$39.90
A sleek pair of black faux leather hot shorts with a mid-rise waist and cheeky hem.
$26.90
A chic black ponte skort with a high-rise waist and flirty front slit for versatile styling.
$34.90
A high-rise grey denim skort with an edgy acid wash and envelope front skirt design.
$30.90
An ivory woven skort with a drop waist and elastic bubble hem over knit shorts.
$44.90
A pair of mid-rise denim jorts with edgy studs and a relaxed fit for stylish adventures.
$29.90
A chic black faux leather short with a lace-up front and cheeky form-hugging fit.
$34.90
A pair of olive mid-rise denim shorts with a trendy lace-up side design for festival flair.
$32.90
A trendy black denim mini skort with a ruched side seam and high-rise waist.
$32.90
A khaki denim skort with a high-rise waist and ruched drawstring for a unique touch.
$39.90
A faux leather mini skort with a western belted waist and form-hugging fit in black.
$9.97 $36.90 73% off
A medium denim skort with a high-rise adjustable belt and flattering pleated A-line silhouette.
$42.90
A pair of black faux leather hot shorts with trendy lace-up sides and a form-hugging fit.
$29.90
A chic pair of black and white gingham ruffle shorts with a flattering low-rise waist.
$34.90
A dark denim mini skort featuring a mid-rise waist and a stylish front skirt overlay with slit.
$36.90
A sassy denim mini skort featuring a unique belted overlay and form-hugging fit.
$34.90
A light denim mid-rise skort combining skirt style with shorts coverage and unique stitch detailing.
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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: S | 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 | Size: XS | 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
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
Windsor The View And You Short Sleeve Tie Back Crop Top in Pink
$9.97
$22.90
56% off
You'll be the cute view in this crop top! It features classic short sleeves, a square neckline, a tie-back design that turns heads, and a fitted crop hem. Complete the look in a midi skirt and sandals for any occasion. Fit & FeaturesDouble-lined brushed knit fabric, moderate stretch, Square neckline, Tie-back design, Fitted crop hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor The View And You Short Sleeve Tie Back Crop Top in Pink | Size: S | Knit Fabric
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: M
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: S
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
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: L
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
Date Night Shorts
When it comes to curating a killer date night look, there’s just something about slipping into a pair of shorts that feels both effortless and electric. Date night shorts aren’t just a wardrobe staple—they’re an open invitation to let your personality shine, to flirt with your own style, and to turn every sidewalk into your personal runway. Whether you’re heading out for rooftop drinks, a spontaneous drive-in movie, or a candlelit dinner al fresco, the right pair of shorts brings that perfect blend of comfort, confidence, and a little bit of mischief. Picture this: you’re getting ready with your besties hyping you up, music blasting, and you reach for those sleek tailored shorts that hug you in all the right places. Suddenly, every mirror selfie is a thirst trap, and you’re already planning your grand entrance. It’s not just about baring a little leg—it’s about showing up as the boldest, most authentic version of yourself, ready to own the night.
Choosing the perfect date night shorts is all about dialing into your vibe and the energy you want to bring. Maybe you love the drama of a high-waisted silhouette paired with a barely-there crop top, or perhaps you’re all about that laid-back glam with breezy, flowy fabrics that catch the light with every step. Think about the details that make you feel unstoppable: a snatched waistband, a flirty hemline, or those cheeky pockets that are perfect for stashing your lip gloss (or your date’s phone number). If you’re shopping for yourself, let your mood lead the way—are you feeling bold and daring, or are you channeling soft romance? Date night shorts also make a seriously cute gift for your ride-or-die bestie, your sister, or anyone who deserves a little extra sparkle in their wardrobe. Gifting a pair of windsor shorts is like handing over a ticket to good times and main character moments—trust, she’ll remember who made her feel like that girl.
No matter how you style them, shorts are a game-changer for those balmy nights when you want to look fire without breaking a sweat. Dress them up with strappy heels and a sleek blazer for instant boss energy, or keep it playful with sneakers and a graphic tee for those spontaneous adventures that always end with laughter and stories for days. The best part? Shorts give you the freedom to dance, strut, and live out your wildest rom-com fantasies, all while serving looks that are equal parts sexy and unapologetically you. If you’re ready to turn up the heat and make every date night unforgettable, check out our full collection of Date Night Outfits for even more inspo and style magic.