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.
$34.90
A pair of medium wash, high-rise denim shorts with a frayed hem and five-button fly closure.
$32.90
A pair of grey acid wash high-rise denim shorts featuring distressed details, frayed hems, and slight stretch.
$34.90
A pair of medium wash high-rise denim shorts featuring distressed accents and a frayed hem.
$13.97 $34.90 60% off
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 featuring distressed details and a relaxed, classic fit.
$32.90
A pair of light wash, high-rise denim shorts featuring a frayed hem and classic five-pocket styling.
$36.90
A dark denim mini skort featuring a high-rise fit, faux wrap overlay, side tie, and frayed hem.
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Windsor Sealed With Charm Short A-Line Dress in White-2
$9.97 $38.90
74% off
Seal your look with this charming A-line dress for a rehearsal dinner or sunset dinner date! The dress features a sleeveless sweetheart neckline, adjustable spaghetti straps, a padded bust, and a flattering short-length hem. Complete the look in chic block heels. Fit & FeaturesSleeveless sweetheart neckline, Adjustable spaghetti straps, Padded bust, A-line silhouette, Short-length hem, Poplin fabric, stretchy knit lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sealed With Charm Short A-Line Dress in White-2 | Size: L | Knit Fabric
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-2 | Size: S | Cotton/Knit Fabric/Rhinestone
Such A Sweetheart Corset Lace-Up A-Line Short Dress in Light Blue
$9.97 $48.90
80% off
Capture sweet vibes in this flirty corset short dress designed with a striking lace-up back design, a corset-style bodice that snatches your waist, and a flattering A-line silhouette. Pair with bow earrings. Fit & FeaturesPoplin woven fabric, woven lining, Sweetheart neckline with adjustable drawstring tie, Adjustable spaghetti straps, lace-up back design, Underwire bust, corset-bodice, flexible boning, Side zipper and hook-eye closure, A-line short silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Such A Sweetheart Corset Lace-Up A-Line Short Dress in Light Blue | Size: L | Woven Fabric
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
Shake it up in this leopard ruffle hot short for a night on the prowl! Fit & FeaturesLeopard print, mesh fabric, stretchy knit lining, High-rise waist, Ruffled silhouette, Form-hugging fit, Runs true to size, Shop The Matching Top: She's A Wild One Leopard Ruffle Tube Top Free Shipping on All Orders Over $75. | Windsor She's A Wild One Leopard Ruffle Hot Shorts | Size: L | Knit Fabric/Mesh Fabric/Mesh Fabric
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
Set the tone in this spicy ruffled hot short with a flattering low-rise waist that flaunts your figure! Pair with the matching top to complete the vibe. Fit & FeaturesMesh-lined fabric, Low-rise waist, Ruffled, fitted silhouette, Runs true to size, Shop The Matching Top: Summer Spice Lace-Up Ruffle Crop Top Free Shipping on All Orders Over $75. | Windsor Summer Spice Low-Rise Ruffle Hot Shorts in Pink | Size: L
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: M
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.