Olive Shorts
Olive shorts are your new wardrobe BFF, ready to bring that cool, laid-back vibe to any outfit you throw together. Whether you're brunching with the squad or hitting up a music festival, these shorts have your back—literally and figuratively! Pair them with a chic crop top for those sun-soaked days or layer up with a cozy sweater when the breeze kicks in. With their versatile hue and effortlessly stylish appeal, olive shorts are the ultimate go-to for every Windsor girl who knows how to keep it fresh and fab.
$14.97 $34.90 57% off
An olive mid-rise cotton skort with a pleated skater overlay and fitted woven shorts.
$34.90
A pair of olive mid-rise denim shorts with a trendy lace-up side design for festival flair.
$32.90
A stylish olive twill skort with a ruched side seam and adjustable drawstring for a custom fit.
$46.90 - $49.90
A chic olive cargo jogger with high-rise waist, metal ring trims, and elastic cuffed hems.
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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
Olive Shorts
Olive shorts are that not-so-secret weapon every wardrobe needs—the kind of piece that plays nice with literally everything you already own but still manages to steal the spotlight. Whether you’re mapping out your next girls’ day adventure or need a quick switch-up for that brunch-to-night-out transition, olive shorts have your back. Their earthy, effortlessly cool vibe makes them a total chameleon; dress them up with a silky cami and layered jewelry for rooftop hangs, or keep it chill with a cropped tee and chunky sneakers for those spontaneous road trips that end with you chasing the sunset. If you’re the type who loves to mix and match, olive shorts become your style playground: they’re the perfect base for bold pops of color, animal prints, or even that oversized blazer you thrifted last week. And let’s talk comfort—high-waisted silhouettes, paperbag waists, or tailored fits, there’s an olive short for every mood and every body. They’re the kind of staple you reach for on repeat, knowing you’ll always look put together without even trying.
Gifting olive shorts? Instant icon move. Whether you’re shopping for your most fashion-forward friend or that sister who’s just discovered her style stride, this is a gift that says “I get you, and I get your vibe.” Olive shorts aren’t just a piece of clothing—they’re an open invitation to experiment, to play, to build a look that’s entirely your own. Imagine your bestie unwrapping a pair and immediately planning her next fit pic, or your cousin texting you a selfie from her weekend getaway, wearing her new fave shorts and absolutely glowing. They’re also a thoughtful pick for the grad who’s about to take on the world, the friend who’s always down for a last-minute festival, or the coworker who’s mastered the art of desk-to-dinner dressing. And if you’re on a mission to build a capsule wardrobe that works as hard as you do, olive shorts are a must-have. They travel light, pack easy, and always serve a look—no matter where you’re headed.
When you’re ready to level up your olive game, don’t sleep on the power of a matching moment. Pair your olive shorts with a crisp white tank, a slouchy denim jacket, or even a flirty crop top for maximum main character energy. And if you want to keep the vibe going, check out our Olive Skirts collection for even more ways to rock this effortlessly chic hue. Olive shorts are more than just a trend—they’re a whole mood, a confidence boost, and a style staple rolled into one. Whether you’re making memories with your ride-or-die crew or just vibing solo, these shorts are here to make every day feel like your best day.