Dressy Shorts
Dressy shorts are your ticket to slay the style game with a mix of elegance and sass. Perfect for those moments when you want to flaunt your legs while keeping it chic, these shorts are the ultimate wardrobe chameleon. Whether you're heading to a brunch date or dancing the night away, dressy shorts have got you covered. Pair them with a sleek blouse or a daring crop top, and watch as you turn heads and steal the spotlight. It's time to step out in confidence and make every sidewalk your runway!
$29.90
A sleek pair of black faux leather high-rise shorts with side pockets and a cheeky hem.
$26.90
A high-rise black metallic faux leather short with cargo pockets and a form-hugging fit.
$54.90
A pair of medium denim high-rise shorts adorned with rhinestone chains and trendy distressed accents.
$29.90
An ivory floral skort with a ruffled tiered silhouette and high-rise smocked waistband.
$34.90
A pair of leopard print hot shorts with sequin embroidery and a cheeky, high-rise fit.
$29.90
A polished pair of pink high-rise trouser shorts with side pockets and a slim-fit silhouette.
$22.90
A sleek black faux leather wrap skort with a high-rise waist and pleated detailing.
$24.90
An ivory lace mini skort with a ruched high waist and flowy A-line hanky hem.
$39.90
A chic brown faux leather skort with a high-rise waist and asymmetric wrap-front design.
$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.
$39.90
A trendy brown faux leather mini skort with a high-rise waist and western buckle accent.
$39.90
A light denim skort with tiered ruffles and a flared silhouette over fitted shorts.
$29.90
An ivory lace skort with tiered ruffles and knit-fitted shorts for charming coverage.
$29.90
A black ponte mini skort with rhinestone bows, high-rise waist, and flirty front slit.
$26.90
A sassy leopard-print faux suede short with a high-rise waist and cheeky fit in brown.
$36.90
A medium denim skort with a dual slit overlay and form-hugging fit for chic styling.
$24.90
An ivory high-rise skort with a flattering A-line silhouette in smooth ponte knit fabric.
$36.90
A medium denim high-rise skort featuring a ruffled mini skirt overlay and form-hugging fit.
$29.90
A pink striped boxer skort featuring a mid-rise waist and form-hugging woven fabric.
$22.90
A chic black satin mini skort featuring a high-rise waist and adjustable ruched side seam.
$26.90
A black knit mini skort with a high-rise waist and romantic lace trim hem.
$39.90
A high-rise black knit skort with a preppy pleated silhouette and striped mini-length hem.
$39.90
A denim mini skort with a mid-rise adjustable belted waist and form-hugging silhouette.
$29.90
A dazzling pair of black hot shorts featuring rhinestone embellishments and a stretchy cotton-blend fabric.
$29.90
A flirty black lace mini skort with tiered ruffles and fitted shorts for a cute look.
$29.90
A black faux leather skort featuring a high-rise waist and dual side slits for a chic look.
$32.90
A chic black mini skort with a high-rise waist, faux leather buckles, and pleated hem.
$15.97 $36.90 57% off
A charcoal woven mini skort with a high-rise waist and pleated A-line silhouette.
$34.90
A black faux leather mini skort featuring high-rise waist and dual front cargo flap pockets.
$32.90
A brown faux suede skort with ruched ruffles and a mid-rise waist for stylish layering.
$36.90
A brown twill woven mini skort with a high-rise waist and double belted pleated overlay.
$36.90
A trendy brown faux suede mini skort with a high-rise waist and front wrap tie.
$29.90
A chic ivory knit skort with a high-rise waist, double bow design, and pleated skater silhouette.
$34.90
A dark denim high-rise skort with a faux wrap-front and fitted shorts for casual style.
$34.90
A brown denim mini skort featuring a high-rise waist and dual front slits for a chic look.
$9.97 $34.90 71% off
A rust denim skort with a mid-rise belted waist and bodycon silhouette for casual occasions.
$15.97 $36.90 57% off
A high-rise ivory knit skort with a pleated silhouette and striped waistband for a preppy look.
$36.90
A grey plaid pleated skort with a drop waist and hidden shorts, crafted from knit fabric.
$19.90
A high-rise black ponte micro short with a form-hugging fit and cheeky cut hem.
$32.90
A trendy black denim mini skort with a ruched side seam and adjustable drawstring.
$26.90
A boho-inspired ivory lace skort with a ruffled drop waist and A-line silhouette.
$39.90
A sleek pair of black faux leather hot shorts with a mid-rise waist and cheeky hem.
$29.90
A black faux leather skort with a drop-waist design and hidden cheeky shorts.
$39.90
A faux leather mini skort with a western belted waist and form-hugging fit in black.
$29.90
A black pleated ponte skort with a high-rise waist and mini-length hem for a preppy look.
$19.90
A pair of black sheer lace shorts with a built-in panty lining for cheeky coverage.
$32.90
A black chiffon skort with rhinestone embellishments, featuring a high-rise waist and tiered ruffles.
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Radiate the sweetest vibe in this adorable hanky hem mini skort! Designed with an airy sheer floral lace fabric and a knit lining, this pretty skort will bring that boho-chic flair. The ruched high waist leads to a hanky hem with an asymmetric design creating an effortless flowy A-line silhouette over fitted shorts. Style with a crop top and mules for a sunset happy hour! Fit & FeaturesStretchy sheer floral lace fabric with knit lining, Ruched high waist, Mini-length hanky hem, A-line fit, Fitted shorts, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweetest Vibe Hanky Hem Lace Mini Skort in Ivory | Size: M | Lace Fabric/Knit Fabric
Capture cool vibes in this on-trend acid-wash denim skort! Designed with a cotton-blend denim fabric, the skort offers a moderate stretch. The flattering mid-rise waist leads to a mini-length overlay over hidden fitted shorts for coverage. The skort features a classic five-pocket and belt loop design and a hidden front zipper and button closure. Style with a graphic tee and combat boots for an edgy-chic concert look. Fit & FeaturesAcid wash cotton-blend denim fabric, moderate stretch, Mid-rise waist, Five-pocket and belt loop design, hidden front zipper, button closure, Mini-length overlay, hidden fitted shorts, Form-hugging fit, Skort in size small has a 10" front rise with a 2" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Keep It Cool Mid-Rise Acid-Wash Denim Skort in Black | Size: XL | Cotton
Cute and trendy, this denim mini skort adds a flirtatious vibe to your 'fits with its tiered ruffled design. The short overlay offers a flared silhouette over hidden fitted shorts for coverage. Fit & FeaturesDenim fabric, Mid-rise waist, back zipper closure, V-shaped waist seam, Tiered ruffled design, Mini-length overlay, flared silhouette, Fitted shorts, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cute Trendsetter Ruffled Denim Skort in Light Denim | Size: M
Bring on the compliments in this high-rise skort featuring a flattering A-line silhouette and mini-length hem. The smooth ponte knit fabric offers a polished look and plenty of stretch. Fit & FeaturesPonte knit fabric, shorts lining, moderate stretch, High-rise waist, A-line silhouette, Mini-length hem, Skort has a 11.5” front rise with a 1.5” inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Admirable Style High-Rise Ponte Mini Skort in Ivory | Size: S | Knit Fabric
Achieve a preppy look with this pleated ponte skort in a flattering high-rise waist and mini-length perfect for showing off boots or flats! Fit & FeaturesPonte knit fabric, shorts lining, High-rise waist, Pleated skirt overlay, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor School's Out High-Rise Pleated Ponte Skort in Black | Size: XS | Knit Fabric
Look and feel charming in this lace skort designed with flirty ruffles and knit-fitted shorts for coverage. Pair with a jean jacket. Fit & FeaturesMesh floral lace fabrication, moderate stretch, Drop waist, Tiered-ruffles, Mini skirt-like overlay, Knit fitted shorts, Skort in size small has an 8" front rise with a 2" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Charming Allure Drop Waist Tiered Lace Skort in Ivory | Size: L | Lace Fabric
Look and feel darling in this ruffled denim skort for daytime fun! Fit & FeaturesMedium wash denim fabric, High-rise waist, front button and zipper closure, belt loops, Form-hugging fit, Ruffled mini skirt overlay, Shorts lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Daylight Darling High-Rise Ruffled Denim Skort in Med Denim | Size: M
A high-rise knit skort features a preppy pleated silhouette and a striped mini-length hem. Perfect for back-to-school or any casual plans. Shop Matching Top And Sweater: Preppy Please Striped V-Neck Crop Top, Preppy Please Striped Button Crop SweaterFit & FeaturesStretchy knit fabric, shorts lining, High-rise waist, Pleated silhouette, Striped mini-length hem, Skort has a 9.5" front rise with a 2" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Preppy Please Striped Pleated Knit Skort in Black | Size: L | Knit Fabric
You're just a girl who loves to look cute and casual, and this striped boxer skort is just the ticket! With a flattering mid-rise waist with button accents and a form-hugging fit, you'll love having this skort in the lineup. Fit & FeaturesStriped print, woven fabric, Elasticized mid-rise waist, button accents, Form-hugging fit, Shorts lining, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Just A Girl Mid-Rise Striped Boxer Skort in Pink | Size: L | Woven Fabric
Wild and flirty, this leopard skort brings fierce charm in a high-rise waist and ruffled design. Perfect for casual nights out or vacations! Fit & FeaturesWoven fabric, leopard print, Stretch smocked high-rise waist, Ruffled design, Skirt overlay, shorts bottom, Runs true to size, Free Shipping on All Orders Over $75. | Windsor She's Wild High-Rise Leopard Ruffle Skort | Size: XS | Woven Fabric
Dressy Shorts
Ready to level up your wardrobe game? Dressy shorts are basically the secret weapon you never knew you needed—until now. Think about it: you’re racing out the door for a rooftop brunch, and you want to look put-together but still feel like you could hop on a bike or dance all night if the mood strikes. Enter the world of dress shorts. These aren’t your basic, lounging-around-the-house shorts; they’re the kind of pieces that make you feel like you’ve got your life together, even if you’re still figuring out what’s for dinner. Whether you’re styling them with a crisp button-down for that big presentation or pairing them with a flirty crop top for your bestie’s birthday bash, dressy shorts are all about giving you options. And honestly, who doesn’t love options? They’re a go-to for the girl who loves to keep her look fresh and unpredictable, who wants to show a little leg while keeping it classy, and who knows that confidence is always the best accessory. If you’re shopping for yourself (because, hello, self-love) or picking up a gift for your ride-or-die who’s always the first to RSVP “yes” to every invite, you can’t go wrong with a pair that’s got a little extra flair.
Let’s get real—dressy shorts are having a major moment because they’re just so easy to wear, but still make you look like you put in the effort. Maybe you’re heading to a cute garden party, or maybe you’ve got a hot date at that new spot everyone’s posting about. Dress shorts let you flex your style muscles without sacrificing comfort. Look for details like pleats, tailored fits, or a cheeky belt to give your outfit that “I woke up like this” energy, but with a polished twist. And don’t even get us started on the versatility—pair them with heels and a blazer for an instant power move, or keep it chill with sneakers and a graphic tee for those spontaneous adventures that always end up being the best stories. These are the shorts you reach for when you want to feel unstoppable, whether you’re taking over the dance floor, owning the group chat, or just living your main character moment. If you’re shopping for a gift, dressy shorts are perfect for the friend who’s always overdressed (in the best way), the sister who borrows your clothes and never gives them back, or even your mom who’s got better style than half your feed. The best part? They’re a blank canvas—ready to be dressed up or down, mixed and matched, and worn on repeat.
If you’re obsessed with keeping your closet on point and want to explore even more ways to serve up fresh looks, check out our Trendy Shorts page for inspo that’ll have you crushing it from day to night. Dressy shorts are all about making bold moves, mixing comfort with confidence, and turning every sidewalk into your personal runway. Whether you’re gifting them or grabbing a pair for yourself, you’re investing in endless outfit possibilities and unforgettable moments. Go ahead—find the pair that makes you feel unstoppable and let the adventures begin.