Distressed High Waisted Jean Shorts
Distressed high waisted jean shorts are your ticket to main character energy—think effortlessly cool, a little rebellious, and totally ready for whatever the day (or night) throws your way. Whether you’re turning heads at brunch or making memories on a spontaneous road trip, these shorts are all about giving your look that perfect edge. Pair them with your favorite crop top or a slouchy tee and get ready to serve attitude with every step. Because let’s be real: when you slip into distressed high waisted jean shorts, you’re not just getting dressed—you’re making an entrance.
$54.90
A pair of medium denim high-rise shorts with rhinestone chains and trendy distressed accents.
$32.90
A pair of grey acid wash high-rise denim shorts with distressed accents and a frayed hem.
$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 with a frayed hem and five-button fly closure.
$34.90
A pair of medium wash high-rise denim shorts featuring distressed accents and a frayed hem.
$34.90
A pair of grey high-rise denim shorts featuring a frayed hem and five-button front closure.
$32.90
A pair of high-rise dark denim shorts with distressed detailing and a relaxed fit.
$32.90
A pair of light wash, high-rise denim shorts featuring a frayed hem and classic five-pocket styling.
$32.90
A pair of white mid-rise denim shorts with distressed accents and a form-hugging fit.
$13.97 $34.90 60% off
A trendy pair of dark denim shorts featuring a mid-rise waist and stylish lace-up front.
$36.90
A dark denim mini skort featuring a high-rise fit, faux wrap overlay, side tie, and frayed hem.
$36.90
A flattering pair of medium denim high-rise shorts with a stylish cross-over hem and slight stretch.
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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: M | 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
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
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
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
Create an iconic 'fit for concerts and festivals with these curve-hugging hot shorts featuring a low-rise waist, front studded trim, and cheeky fit. Fit & FeaturesWoven fabric, moderate stretch, Low-rise elasticized waist, Front-studded trim, Cheeky form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Iconic 'Fit Studded Hot Shorts in Black | Size: S | Woven Fabric
Turn up the heat in these ponte micro shorts this season! Featuring a high-rise waist for a flattering fit, a form-hugging silhouette to accentuate your curves, and a cheeky cut to show off those legs. Complete the look in a graphic tee and sneakers! Fit & FeaturesPonte fabric, minimal stretch, High rise waist, Form-hugging fit, Cheeky cut micro hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Make It Hot High Rise Ponte Micro Shorts in Black | Size: XL
Show off a trendsetting vibe in these mid-rise denim shorts for festival season! The lace-up side design adds the perfect edge to your casual 'fits. Fit & FeaturesDenim fabric, moderate stretch, Mid-rise waist, belt loops, Front button and hidden zipper closure, Lace-up side design, Fitted, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Trendsetting Vibe Lace-Up Denim Shorts in Olive | Size: L
Distressed High Waisted Jean Shorts
Distressed high waisted shorts are the ultimate partner-in-crime for those days when you want to look like you just rolled out of your best life and didn’t even have to try. These shorts bring a little edge to your vibe with their frayed hems, artful rips, and that iconic high-rise fit that hugs your waist just right. Whether you’re showing up to brunch with your ride-or-dies, catching the last bit of golden hour, or just taking over the city one iced coffee at a time, these shorts are your go-to for effortless cool. There’s something about slipping into distressed high waisted shorts that makes you feel fearless—like you’re ready to chase adventure, flirt with a little trouble, and take on whatever the day throws your way. They’re the kind of staple that fits right in at backyard hangs, rooftop parties, music festivals, or spontaneous road trips. And if you’re hunting for the perfect gift, trust—these shorts are a no-brainer for your bestie who loves to stand out, your sister who’s always borrowing your clothes, or anyone who wants to add a little attitude to their closet.
When it comes to picking your dream pair, it’s all about the details. The best distressed high waisted shorts are the ones that feel like they were made for you—snug at the waist, a little loose at the thigh, and just the right amount of distressing to show off your wild side without going overboard. Look for sturdy denim that holds its shape but still lets you move (because you never know when a dance break might happen). Pockets are a must for stashing your phone, lip gloss, or that secret note from your crush. And don’t sleep on the wash—whether you’re into classic blue, faded black, or something a little bolder, the right color can totally change your vibe. These shorts are the ultimate blank canvas: throw them on with a crop top and sneakers for a downtown-cool look, or dress them up with a blazer and heels when you’re feeling extra. They’re also perfect for layering—think oversized hoodies, vintage tees, or a killer moto jacket when the nights get breezy. And if you’re obsessed with the high-waisted fit but want a little more coverage, check out our Distressed High Waisted Boyfriend Jeans for that same fearless energy in a full-length silhouette.
Owning a pair of distressed high waisted shorts is like having a cheat code for confidence. You’ll find yourself reaching for them on repeat, whether you’re running errands, hitting up your favorite taco spot, or heading out for a spontaneous adventure with your crew. They’re made for making memories and breaking hearts, for those days when you want to look as bold as you feel. If you’re gifting them, you’re basically handing over a ticket to main character energy—because everyone deserves to feel unstoppable, even on the most ordinary days. So go ahead and claim your spot as the best-dressed bad influence in your group chat. With the right pair of distressed high waisted shorts, you’re always ready for whatever comes next.