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.

Show Filters

Sort: Recommended

Size

Color

Price

All Filters

27 results

Sort

Sale

Windsor Cool Edge High-Rise Distressed Denim Shorts in Grey

$9.97 $32.90 70% off

A pair of grey acid wash denim shorts featuring a high-rise waist, distressed accents, and frayed hems.

Sale

Cool Classic High-Rise Frayed Denim Shorts in Grey

$9.97 $34.90 71% off

A pair of grey high-rise denim shorts featuring a frayed hem and five-button front closure.

Windsor Sun’s Out, Shorts On High-Rise Denim Shorts in Med Denim

Sale

Windsor Sun’s Out, Shorts On High-Rise Denim Shorts in Med Denim

$13.97 $34.90 60% off

A pair of medium wash high-rise denim shorts featuring distressed accents and a frayed hem.

Windsor Cut to Chill High-Rise Denim Shorts in Light Denim

Sale

Windsor Cut to Chill High-Rise Denim Shorts in Light Denim

$13.97 $32.90 58% off

A pair of light wash, high-rise denim shorts featuring a frayed hem and classic five-pocket styling.

Exceptional Poise High Rise Denim Shorts in Dark Denim

$36.90

A pair of high-rise dark denim shorts with a form-hugging fit and stretch fabric.

Now Trending

Sale

Windsor Sealed With Charm Short A-Line Dress in White-2

$9.97 $38.90
74% off

(34)

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

Windsor Smooth Moves PU High-Rise Shorts in Black

$29.90

(32)

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

Windsor Chic Fairytale Tiered Lace Hot Shorts in Ivory

$29.90

(27)

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 Ivory | Size: M | Knit Fabric/Mesh Fabric

Windsor Center Stage Rhinestone Hot Shorts in Black-2

$29.90

(11)

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: XS | Cotton/Knit Fabric/Rhinestone

Exceptional Poise High Rise Denim Shorts in Dark Denim

$36.90

(9)

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

One And Only Mid-Rise Hot Shorts in Black

$24.90

(5)

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: XS | Woven Fabric

Olessa Short Sleeve A-Line Slit Satin Formal Dress in Navy Blue

$59.90

(4)

The silky satin and curve-flattering silhouette make the Olessa formal dress feel so special! The dress boasts adorable flutter short sleeves and a chic A-line silhouette with a high front slit for effortless movement. Fit & FeaturesPremium satin fabric, woven lining, Short flutter sleeves, V-neckline, padded bra cups, Back zipper and hook-eye closure, High front slit, A-line silhouette, floor-length hem, Runs true to size, Where to Wear:Prom, weddings, bridesmaids, galas, black tie parties, engagement parties, rehearsal dinner, fancy date nights, big milestone celebrations Free Shipping on All Orders Over $75. | Windsor Olessa Short Sleeve A-Line Slit Satin Formal Dress in Navy Blue | Size: S | Satin Fabric

Summer Spice Low-Rise Ruffle Hot Shorts in Black

$29.90

(3)

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 Black | Size: M

She's A Wild One Leopard Ruffle Hot Shorts

$29.90

(3)

Shake it up in this leopard ruffle hot short for a night on the prowl! Shop Matching Top: She's A Wild One Leopard Ruffle Tube TopFit & FeaturesLeopard print, mesh fabric, stretchy knit lining, High-rise waist, Ruffled silhouette, Form-hugging fit, Runs true to size, 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

Windsor Maybe Tonight Leopard Ruffle Shorts

$29.90

(3)

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: M | Knit Fabric

Distressed High Waisted Jean Shorts

Distressed high waisted jean shorts are the ultimate confidence-boosters for the girl who lives for a little edge in her everyday. These are the shorts that turn every sidewalk into a runway and make every mirror selfie a double-tap moment. With their perfectly frayed hems, artfully placed rips, and that just-right high rise, they’re the go-to for anyone who knows that comfort and killer style don’t have to be a trade-off. Whether you’re styling them with a cropped graphic tee and chunky sneakers for a laid-back coffee run or dressing them up with a slinky bodysuit and strappy heels for a night out, high waisted distressed denim shorts are the chameleons of your closet—ready to play nice or turn up the heat, depending on your mood. There’s an undeniable freedom in slipping into a pair of destroyed high waisted shorts: you instantly feel like you can take on the world, dance in the front row, or make an entrance at brunch with your squad. They’re not just a piece of clothing—they’re a whole vibe, a little bit rebellious, and a lot iconic.

Choosing the right pair is all about knowing what makes you feel unstoppable. Some Windsor girls love a super high waist that cinches everything in and gives you legs for days, while others want a more relaxed fit that’s all about that effortless, borrowed-from-the-boys energy. Look for details that speak to your personal style—maybe it’s a raw hem that looks like you DIY’d it yourself, or strategic distressing that hints at vintage finds from your favorite thrift adventures. Pockets, button-fly closures, and the perfect amount of stretch can all make a huge difference, especially if you’re planning to wear your high waisted distressed denim shorts from sunrise to last call. And let’s talk gifting: if you’ve got a bestie who’s obsessed with festival fashion, or a sister who’s all about that casual-cool look, these shorts are the ultimate present. They’re a wardrobe staple that works for so many occasions—think impromptu road trips, rooftop hangs, or just leveling up your everyday style. And if you’re the type who loves to stand out, try pairing your distressed high waisted shorts with bold accessories, oversized sunnies, or a statement belt for a look that’s all you.

If you’re ready to embrace that fearless, fun-loving energy, exploring the world of high waisted denim shorts distressed is a must. These shorts are made for making memories, turning heads, and giving you that extra dose of main character energy whenever you need it. Whether you’re curating your closet for spontaneous adventures or just want a reliable piece that goes with everything, distressed high waisted shorts are here to back you up—no permission slips required. For even more inspo and options that’ll have you feeling like the best-dressed girl in every room, check out the full collection at Womens High Waisted Distressed Shorts and get ready to step into your next obsession.

Reset Your Password

Email Sent

Order Status

Distressed High Waisted Jean Shorts

Home Distressed High Waisted Jean Shorts

Now Trending

Distressed High Waisted Jean Shorts

Related Collections