Comfortable High Rise Jeans
Comfortable high rise jeans are your new ride-or-die for those days when you want to look effortlessly cool and feel like you’re living in sweats—minus the actual sweats. Slip into that sky-high waist, let your confidence do the talking, and get ready to strut through life with major main character energy. Whether you’re running from brunch to late-night plans or just owning your everyday vibe, these jeans have got your back (and your curves). Why settle for basic when you can be comfy, cute, and totally unstoppable?
$42.90
A pair of medium denim high-rise boyfriend jeans with trendy knee slits and multi-button closures.
$49.90
A pair of black high-rise cargo denim jeans with a straight-leg silhouette and trendy flap pockets.
$46.90
A stylish pair of medium denim jeans with a high-rise waist and straight cropped silhouette.
$46.90
A pair of high-rise boyfriend jeans in denim with distressed accents and a cuffed hem.
$49.90
A high-rise denim cargo jeans with a straight-leg silhouette and eight-pocket styling.
$44.90
A high-rise black denim knit cargo jean with vertical seams and a straight-leg hem.
$44.90
A pair of dark denim high-rise bootcut jeans with a slim fit and slight stretch for comfort.
$44.90
A pair of light denim bootcut jeans featuring a high-rise waist and flattering seam detailing.
$42.90
A pair of light denim skinny jeans featuring a high-rise waist and sculpting, non-stretch fit.
$42.90
A pair of medium denim high-rise mom jeans with distressed knee slits and a skinny leg fit.
$49.90
A dark denim high-rise pant featuring a pinstripe pattern and flattering wide-leg silhouette in denim fabric.
$59.90
A pair of black high-rise straight leg jeans featuring rhinestone cutout trim and a heart-shaped bum seam.
$46.90
A high-rise dark denim jean with a hip-hugging fit and stylish flare hem.
$18.97 $46.90 60% off
A light denim high-rise jean with unique seam detailing and a trendy flare hem.
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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: 3
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
Comfortable High Rise Jeans
Ready to live your best denim life? Comfortable high rise jeans are the ultimate wardrobe MVP, always stepping up for you whether you’re out chasing the sunrise or winding down with your crew. There’s something magic about slipping into a pair that hugs you just right—snug in all the right places, with a waistline that actually stays put (no more awkward tugging, thank you very much). High rise jeans are the jeans you grab when you want to feel a little bit taller, a lot more confident, and totally in control of your vibe. They’ve got that built-in confidence boost, cinching your waist and smoothing your silhouette, so you can strut into the day ready to own it. And when comfort is the name of the game, soft stretch denim and dreamy fits mean you can move, dance, and drop it low at brunch without a second thought. Whether you’re running errands, heading to class, or showing up for a spontaneous adventure, these jeans are the definition of “effortless cool”—the kind of staple you’ll want to live in, day after day.
Picking your perfect pair is all about knowing your style and what makes you feel unstoppable. If you’re gifting, high rise jeans are a go-to for your bestie, your sister, or even your mom (because let’s be honest, everyone deserves a pair that makes them feel like a main character). Think about what they love: are they into a classic, clean look or do they live for a little edge with distressing and frayed hems? The beauty of high rise jeans is how they play nice with literally everything in your closet—crop tops, graphic tees, oversized sweaters, or that statement bodysuit you’ve been dying to debut. They’re the jeans you throw on for a spontaneous road trip, a rooftop hangout, or just a comfy-cute day running around town. And if you’re all about switching up your silhouette, don’t sleep on the drama of High Rise Wide Leg Jeans—they bring major energy and an instant upgrade to your denim game.
Every Windsor girl knows that comfort never has to come at the expense of style. High rise jeans are proof that you can have it all: soft, stretchy fits that keep you cozy, trendy designs that turn heads, and the versatility to dress up or down in seconds. Whether you’re stacking up your denim drawer or searching for that one pair you’ll wear on repeat, these jeans are ready for whatever you throw their way. From sun-up coffee runs to late-night ice cream dates, they’re always down for a good time. So go ahead—find your next favorite fit, hype yourself up, and let your jeans do the talking.