High Rise Casual Shorts
High Rise Casual Shorts are your ticket to main character energy, babe. Whether you’re planning a spontaneous road trip or just want to turn the grocery store into your runway, these shorts have your back (and your best angles). Slip into a pair and instantly level up your confidence—because who says casual can’t be iconic? Get ready to serve looks, break hearts, and live your best life one high rise at a time.
$29.90
A sleek pair of black faux leather high-rise shorts with side pockets and a cheeky hem.
$36.90
A pair of high-rise dark denim shorts with a form-hugging fit and stretch fabric.
$26.90
A pair of black metallic faux leather shorts with a high-rise waist and cargo flap pockets.
$54.90
A glamorous pair of medium denim shorts featuring rhinestone chains and a flattering high-rise waist.
$26.90
A pair of off-white high-rise shorts with a ruffled tier design and stretchy smocked waistband.
$29.90
A pair of high-rise leopard print shorts featuring a playful ruffled hem for bold, stylish nights.
$34.90
A pair of leopard print hot shorts with sequin embroidery and a cheeky, high-rise fit.
$19.90
A high-rise black ponte micro short with a form-hugging fit and cheeky cut hem.
$36.90
A dark denim mini skort featuring a high-rise fit, faux wrap overlay, side tie, and frayed hem.
$39.90
A chic pair of ivory eyelet lace shorts featuring a high-rise waist and dual front pockets.
$32.90
A pair of light denim high-rise shorts with trendy distressed accents and a frayed cut-off hem.
$34.90
A pair of medium wash, high-rise denim shorts featuring a frayed hem and five-button fly closure.
$12.97 $29.90 57% off
A polished pair of pink high-rise trouser shorts with side pockets and a slim-fit silhouette.
$36.90
A pair of multi-color watercolor woven shorts featuring a high-rise waist and relaxed fit.
$29.90
A leopard print ruffle hot short with a high-rise waist and form-hugging fit.
$32.90
A pair of grey acid wash high-rise denim shorts with distressed accents and a frayed hem.
$26.90
A pair of black gauze shorts featuring a high-rise smocked waist and tiered ruffled design.
$32.90
A pair of high-rise dark denim shorts with distressed detailing and a relaxed fit.
$34.90
A pair of medium wash high-rise denim shorts featuring distressed accents and a frayed hem.
$26.90
A taupe knit short with a high-rise waist and trendy scalloped hem for a boho vibe.
$32.90
A pair of dark denim high-rise shorts with a form-hugging fit and four-pocket styling.
$29.90
A pair of chartreuse cotton shorts featuring a high-rise elastic waist, dual front pockets, and fitted silhouette.
$34.90
A pair of grey high-rise denim shorts featuring a frayed hem and classic five-pocket styling.
$32.90
A pair of light denim high-rise shorts featuring a frayed hem, five pockets, and classic fit.
$24.90
An elegant black high-rise skort with a flattering A-line silhouette in stretchy ponte knit fabric.
$29.90
An ivory ponte skort with rhinestone bows, high-rise waist, and a flirty bodycon silhouette.
$46.90
A black high-rise denim skort featuring buckle front detailing and a bodycon mini-length silhouette.
$36.90
A high-rise black denim skort with a wrap design and functional cargo pockets.
$39.90
A high-rise black knit skort with a preppy pleated silhouette and striped mini-length hem.
$36.90
A brown twill woven mini skort with a high-rise waist and double belted pleated overlay.
$29.90
A white high-rise denim skort with a faux wrap-front, hidden shorts, and minimal stretch cotton-blend fabric.
$34.90
A brown denim mini skort with a high-rise waist and dual front slits for a chic look.
$44.90
An ivory woven mini skort featuring a high-rise belted waist, ruffled overlay, and shorts lining.
$34.90
A yellow woven mini skort featuring a high-rise waist, side button accents, and a flirty ruffled hem.
$34.90
A high-rise grey denim skort with an edgy acid wash and envelope front skirt design.
$34.90
A white high-rise denim skort with a wrap front and belt for a flattering, edgy look.
$24.90
An off-white high-rise skort with a flowy silhouette and charming uneven lace trim hem.
$39.90
A khaki denim skort with a high-rise waist and ruched drawstring for a unique look.
$19.90
A playful pair of white high-rise pajama shorts in soft ribbed knit with a hot dog print.
$42.90
A high-rise denim skater skort with a contrast tie-front waistband, pleating, and hidden fitted shorts.
$36.90
A high-rise denim skort with front patch pockets, stretchy knit shorts lining, and a sleek bodycon fit.
$29.90
A black high-rise pleated skort in ponte knit fabric, combining skirt style with shorts comfort.
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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 in Pink | Size: M | Knit Fabric/Mesh Fabric
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 | Size: XS | Cotton/Knit Fabric/Rhinestone
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
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: M | Woven Fabric
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: M
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: S
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: S
Designed with the best fit, these high-rise denim shorts are forever flattering! With a form-hugging fit and a cross-over hem that elevates your everyday look. Fit & FeaturesMedium wash denim fabric, slight stretch, High-rise waist, Front button and hidden zipper closure, belt loop accents, Two back pockets, Form-hugging fit, Cross-over hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Crossed Over High-Rise Denim Shorts in Med Denim | Size: S
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: L | Knit Fabric
High Rise Casual Shorts
High rise casual shorts are the ultimate MVP in a Windsor girl’s wardrobe—seriously, they’re the besties you didn’t know you needed until you’re living in them. Whether you’re strutting through the city, hitting up a last-minute brunch with your crew, or just vibing out at a backyard hang, these shorts always deliver that perfect blend of comfy and cute. The high rise cut cinches your waist just right, giving you that snatched look that pairs effortlessly with everything from slouchy graphic tees to cropped tanks that show off your glow. And let’s be real: there’s nothing like slipping into a pair of shorts that make you feel like you could take on the world (or at least the group chat’s weekend plans). They’re the go-to for those days when you want to look put together but still feel like you could drop into a spontaneous dance party at any second. Whether you’re all about the classic denim vibe or leaning into soft, flowy fabrics that move with you, high rise casual shorts are designed for maximum versatility, keeping you ready for whatever the day throws your way.
Shopping for the perfect pair is all about finding your vibe and dialing up your confidence. If you love to keep things classic with a little edge, check out styles with distressed details or frayed hems—they’re basically a love letter to your inner cool girl. For the babes who are all about comfort, look for soft fabrics with a hint of stretch, or opt for paperbag waists and tie belts that bring a little extra drama to your OOTD. High rise casual shorts are also a total win as gifts—think birthdays, graduations, or just because your bestie deserves to feel like the main character. They’re a staple for students running between classes, creatives on the move, and anyone who wants to keep it cute while conquering the day. And if you’re feeling a little bold, you can even dress them up with a blazer and heels for a night out that’s equal parts effortless and iconic. The beauty of high rise casual shorts is in their ability to flex with your plans—throw them on with sneakers for a coffee run or slide into strappy sandals when you’re ready to turn heads. If you’re craving a little inspo, don’t miss our collection of High Rise Cut Off Denim Shorts for that perfect blend of laidback and luxe.
The best part? High rise casual shorts are all about making you feel unstoppable—like you’re the main event, not just a guest at the party. They’re the piece you reach for when you want to show off your favorite statement belt, tuck in a flowy blouse, or just let your legs steal the show. And because Windsor girls don’t do boring, there’s a style for every mood—whether you’re feeling flirty, fearless, or somewhere in between. Don’t be surprised if your friends start asking where you got your shorts (and then copy your whole vibe). These are the shorts that turn errands into adventures and lazy afternoons into legendary hangs. So go ahead, mix and match, layer up your jewelry, and let your personality shine—because high rise casual shorts are here to keep you looking and feeling like the icon you are, every single day.