Dressy Skorts
Dressy skorts are the ultimate fusion of style and sass, perfect for our Windsor girl who’s ready to conquer any scene with flair. These chic hybrids deliver the elegance of a skirt with the comfort and confidence of shorts, making them your go-to for everything from brunch dates to dance floors. Whether you're twirling under city lights or strutting through sunlit streets, dressy skorts ensure you’re always on point. So step into these versatile wonders and let your fearless fashionista spirit shine!
$39.90
A chic brown faux leather skort with a high-rise waist and asymmetric wrap-front design.
$24.90
An ivory lace mini skort with a ruched high waist and flowy A-line hanky hem.
$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.
$9.97 $24.90 60% off
A black mid-rise skort with a bow slit overlay, offering a form-hugging fit and mini-length hem.
$26.90
A black plaid pleated micro skort with a belted waist and hidden shorts for a preppy look.
$24.90
An A-line high-rise black skort in ponte knit offers a polished look with moderate stretch.
$29.90
An ivory floral skort with a ruffled tiered silhouette and high-rise smocked waistband.
$22.90
A chic black satin mini skort featuring a high-rise waist and adjustable ruched side seam.
$39.90
A high-rise black knit skort with a preppy pleated silhouette and striped mini-length hem.
$26.90
A black knit mini skort with a high-rise waist and romantic lace trim hem.
$32.90
A chic black ponte mini skort with a high-rise waist and faux leather buckle accents.
$29.90
A flirty black lace mini skort with tiered ruffles and fitted shorts for festival fun.
$14.97 $34.90 57% off
An olive cotton skort with a pleated skater overlay and fitted woven shorts for stylish coverage.
$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.
$29.90
A chic ivory knit skort with a high-rise waist, double bow detail, and pleated skater silhouette.
$36.90
A grey plaid pleated skort with a drop waist and hidden shorts, crafted from knit fabric.
$15.97 $36.90 57% off
A high-rise ivory knit skort with a pleated silhouette and striped waistband for a preppy look.
$26.90
A boho-inspired ivory lace skort with a ruffled drop waist and A-line silhouette.
$32.90
A black faux leather mini skort with a high-rise waist and pleated silhouette for stylish outings.
$29.90
A black pleated ponte skort with a high-rise waist and mini-length hem for a preppy look.
$32.90
A black chiffon skort with rhinestone embellishments, featuring a high-rise waist and tiered ruffles.
$29.90
An edgy black acid-wash denim skort featuring a mini-length overlay and hidden shorts for coverage.
$39.90
A medium denim skort featuring a pleated mini skirt overlay and edgy exposed pockets.
$30.90
An ivory woven skort with a drop waist and elastic bubble hem over knit shorts.
$13.97 $32.90 58% off
A chic charcoal skort with a high-rise fit, drop waist, and pleated A-line overlay.
$9.97 $29.90 67% off
A camel faux suede skort with a high-rise belted waist and built-in shorts lining.
$32.90
A trendy leopard-printed mini skort with a mid-rise waist and hidden fitted shorts.
$39.90
A grey plaid mini skort featuring a high-rise fit, pleated overlay, and thin belted design.
$29.90
A black knit mini skort with a high-rise waist, pleated silhouette, and contrast bow tie trim.
$32.90
A stylish olive twill skort with ruched side seam and adjustable drawstring for a custom fit.
$26.90
A black high-rise ponte skort with a flirty front slit and bodycon silhouette.
$9.97 $32.90 70% off
A sleek black faux leather skort with a trendy tie-waist and form-hugging mini silhouette.
$27.90
A black ponte mini skort with a high-rise waist and dual front slits for a chic look.
$22.90
A sleek black faux leather wrap skort with a high-rise waist and pleated detailing.
$34.90
A black acid-wash denim skort with a mid-rise waist and hidden fitted shorts for coverage.
$34.90
A trendy dark denim mini skort with a mid-rise waist and bodycon fit for versatile styling.
$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.
$22.90
A sleek black bodycon mini skort with faux leather fabric and a high-rise waist.
$36.90
A medium denim skort featuring a dual slit skirt overlay and form-hugging fit with slight stretch.
$36.90
A medium denim high-rise skort featuring a ruffled mini skirt overlay and form-hugging fit.
$39.90
A denim mini skort with a mid-rise adjustable belted waist and form-hugging silhouette.
$34.90
A black faux leather mini skort with high-rise waist and dual front cargo flap pockets.
$15.97 $36.90 57% off
A charcoal woven mini skort with a high-rise waist and pleated A-line silhouette.
$36.90
A trendy brown faux suede mini skort with a high-rise waist and front wrap tie.
$34.90
A dark denim high-rise skort with a faux wrap-front and fitted shorts for a trendy casual look.
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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 Skorts
When it comes to leveling up your look with zero effort and maximum impact, dressy skorts are the ultimate power move. Imagine this: you’re heading out for a night that starts with dinner and ends who-knows-where, and you want all the polish of a skirt with the freedom to dance, dash, or drop it low without a single worry. That’s the magic of a dressy skort—effortlessly elegant, endlessly versatile, and always ready to keep up with your most spontaneous plans. Whether you’re styling up for a rooftop party, a brunch date that turns into a shopping spree, or you just want to look like the main character at your next girls’ night, women’s skorts dressy options have your back (and your legs, let’s be real). Picture yourself twirling in a skort elegant enough for a cocktail event but comfy enough for an afterparty—no awkward moments, just pure confidence and a little bit of that “I know I look good” energy.
Dressy skorts for women are basically the secret weapon for anyone who wants to serve looks and live their best life, all at once. They’re the perfect pick for gifting, too—think about it: your bestie’s birthday, a graduation celebration, or just a “you deserve a treat” surprise. Everyone loves an upgrade that feels luxe but lets you move like you’re still in your favorite shorts. The fit is flattering on so many body types, and the styling options are endless—pair with a sparkly cami, a tailored blazer, or even a graphic tee for that “I just threw this on” vibe (but, like, you definitely planned it). A dressy skort can go from day to night, casual to glam, with just a switch of shoes or a swipe of bold lipstick. And if you’re all about options, don’t forget to check out our Dressy Mini Skirts for even more ways to turn heads and break hearts.
If you’re the girl who wants to look put-together without sacrificing comfort, or the friend who always has a backup plan (and a backup outfit), dressy skorts are your new BFF. They’re made for those moments when you want to feel unstoppable—whether you’re making an entrance at a formal event or just living it up with your crew. The best part? You never have to worry about wardrobe malfunctions or sitting out on the fun. With a skort elegant enough to impress but practical enough to keep up with your wild side, you’re free to be bold, fearless, and totally yourself. So go ahead—step out, stand out, and let your dressy skort do the talking.