Distressed High Waisted Boyfriend Jeans
Distressed high waisted boyfriend jeans are your new excuse to break the rules and look good doing it. Effortlessly cool and forever on-trend, these jeans bring that IDGAF energy to every outfit—perfect for when you want to keep it casual but still turn heads. Whether you’re rolling with your crew or taking yourself out (because, duh, you deserve it), these jeans have your back with a vibe that says “I woke up like this” and totally meant it.
$42.90
A pair of medium denim high-rise boyfriend jeans with trendy knee slits and multi-button closures.
$46.90
A medium denim high-rise boyfriend jean with destructed detailing and moderate stretch for trendsetters.
$46.90
A stylish pair of medium denim high-rise straight cropped jeans with knee destruction and moderate stretch.
$46.90
A high-rise boyfriend jean in vintage-inspired denim with distressed accents and a cuffed hem.
$42.90
A pair of high-rise medium denim mom jeans with distressed knee slits and a skinny leg fit.
$44.90
A pair of black high-rise acid wash cargo jeans with a straight-leg hem and cargo pockets.
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Create a dramatic moment with distressed jeans that add an edge to your look! The medium-wash denim jeans feature a flattering high-rise waist and a boyfriend silhouette with trendy knee slits. Complete the look with a crop top and combat boots. Fit & FeaturesHigh-rise waist, Boyfriend silhouette , Knee slit accents, Multi-button down closures, Five-pocket styling, belt loop accents, Medium-wash denim, slight stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor High-Rise Distressed Boyfriend Jeans in Medium Denim | Size: 1
Step out in style in these high-rise mom jeans. These medium-wash denim jeans are a wardrobe must-have with a high-waist silhouette and mom jean fit. The ripped detailing at the knees strikes the perfect balance of edge and elevated denim style that perfectly pairs back to a blazer or sleek bodysuit for a versatile but always chic look. Fit & FeaturesMedium wash denim, color fading, no stretch, High-rise waist, Five-pocket styling, belt loop design, Front button and hidden zipper closure, Mom-styled skinny leg, Distressed accents, knee slits, Runs true to size, Free Shipping on All Orders Over $75. | Windsor High-Rise Distressed Mom Skinny Jeans in Medium Denim | Size: 11
Capture effortless-cool style in these cargo denim jeans perfect for casual wear! They feature a flattering high-rise waist and straight-leg silhouette with trendy cargo flap pockets, seam detailing, and medium-wash denim fabric. Complete the look with a graphic tee and sneakers! Fit & FeaturesHigh-rise waist, Straight-leg silhouette, Side and back cargo flap pockets, seam detailing, Front button and hidden zipper closure, Belt loop accents, three-pocket styling, Medium wash denim fabric, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cool Captured High Rise Cargo Denim Jeans in Black | Size: M
Strut in the Rocky High-Rise Destructed Boyfriend Jeans and make it known who the true trendsetter is! Featuring a high waist and destructed detailing, this pair of denim is perf for a shopping day. Take your look up a notch for a nice dinner by adding on heels and a mini tote! Fit & FeaturesDenim fabric, moderate stretch, High-rise waist, Destructed detailing, Boyfriend fit, Button-front closure, hidden zipper closure, Traditional five-pocket and belt loop design, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Rocky High-Rise Destructed Boyfriend Jeans in Medium Denim | Size: 13
Serve major style in these fabulous straight cropped jeans by Windsor Denim! They feature a flattering high-rise waist, a straight-leg silhouette, knee destruction accents, and a front cut-off style cropped hem. The medium-wash denim fabric offers a moderate stretch for comfortable wear. Complete the look in a cute corset top for a casual dinner! Fit & FeaturesHigh-rise waist, Straight-leg silhouette, knee destruction accents, Front cut-off cropped hem, Front button, hidden zipper closure, Five-pocket styling, belt loop accents, Medium-wash denim fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | High-Rise Straight Cropped Jeans by Windsor Denim in Medium Denim | Size: 3
Put your curves on display in these figure-flaunting mid-rise denim jeans showcasing an accentuating seam detail and a flared hem. Fit & FeaturesDark wash denim fabric, slight stretch, Mid-rise waist, Hip-hugging fit, seam detailing, Flare hem, Front button and hidden zipper closure, Three-pocket styling, belt loop accents, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Make A Scene Mid-Rise Flare Denim Jeans in Dark Denim | Size: 5
It'll be hard for people not to notice you in these cool camouflage denim jeans with an on-trend low-rise waist and convenient cargo pockets. Fit & FeaturesCamouflage print, denim fabric, Low-rise waist, Straight-leg silhouette, Cargo side pockets, Front button and zipper closure, belt loops, pockets, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Off The Radar Camouflage Straight Leg Denim Jeans in Grey | Size: M
Prepare to love styling every top with these high rise boyfriend denim jeans featuring trendy distressed accents and a cuffed hem. Complete the look with a cute top and mules. Fit & FeaturesVintage-inspired denim fabric, minimal stretch, High-rise waist, Boyfriend fit, Distressed accents, Cuffed hem, Front button and hidden zipper closure, Belt loop accents, five-pocket styling, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Prepare To Love High RIse Boyfriend Denim Jeans | Size: 3
Forever flattering and trending, these mid-rise wide-leg denim jeans add an edge to your everyday look. Fit & FeaturesLight wash denim, Mid-rise waist, front button and zipper closure, Belt loop accents, Relaxed wide-leg silhouette, Five-pocket styling, Runs true to size, Free Shipping on All Orders Over $75. | Windsor On Trend Mid-Rise Wide-Leg Denim Jeans in Light Denim | Size: S
Step up your cuteness in these cargo denim jeans with pockets perfect for stashing your lip gloss or phone and a flattering straight-leg silhouette. Fit & FeaturesDenim fabric with color fade effect, High-rise waist, front button and hidden zipper closure, Straight-leg silhouette, Cargo style, Eight-pocket styling, belt loop accents, Front button closure, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cutie In Cargo High-Rise Denim Jeans | Size: S
Distressed High Waisted Boyfriend Jeans
Distressed high waisted boyfriend jeans are the ultimate ride-or-die denim for the girl who isn’t afraid to leave her mark—literally. These jeans have that effortlessly undone vibe that says, “Yeah, I woke up like this,” while still serving major style energy. The high waist snatches you in, gives your curves a little extra love, and makes every crop top, bodysuit, or oversized tee look like a whole moment. The relaxed boyfriend fit? Pure comfort, babe—think brunches that turn into spontaneous road trips, late-night food runs, and dance parties in your living room. Those perfectly placed rips and frays aren’t just a detail; they’re a mood. Each distressed patch tells a story, and you get to decide if it’s from a wild night out, a chill day with your crew, or just because you love a little edge. Whether you’re styling them with chunky sneakers for a laid-back vibe or strappy heels for a “didn’t try but totally nailed it” look, these jeans are all about versatility and attitude.
If you’re on the hunt for the best distressed boyfriend jeans, here’s the tea: It’s all about the fit and the feel. High waisted ripped boyfriend jeans are a closet staple for anyone who wants to keep it cool but still look put-together. They’re a go-to for the girl who’s always first in the group chat with the brunch plans, the one who’s got the playlist for every mood, and the friend who never says no to a little adventure. These jeans make an epic gift for your bestie who’s always borrowing your clothes, your sister who needs a style upgrade, or even for yourself—because honestly, self-gifting is self-care. The high waist works magic for every body type, giving you that just-right fit without sacrificing comfort. And when you want to switch things up, distressed boyfriend jeans pair with literally anything: graphic tees, silky camis, chunky knits, or a classic white tank. Add a leather jacket and you’re ready to take on the world (or at least your next coffee run).
When you’re living for those laid-back days or planning a look that says “chill but still a big deal,” distressed high waisted boyfriend jeans are your forever fave. They’re made for those moments when you want to look cute without trying too hard—think catching golden hour with your girls, hitting up a rooftop hang, or just vibing in your favorite sneakers. If you’re feeling the distressed denim obsession but want something a little lighter, don’t sleep on our Distressed Mid Rise Denim Shorts for those days when you want to show a little more leg. No matter how you style them, these jeans are all about confidence, comfort, and a little bit of mischief—because the best looks are the ones that make you feel unstoppable.