Boyfriend Jeans
Ready to rock that effortlessly cool, laid-back vibe? Boyfriend jeans are your go-to for nailing that perfect blend of casual and chic. Whether you're hitting the streets or lounging with your squad, these jeans have got you covered with their relaxed fit and undeniable style. Pair them with a cute crop top or an oversized sweater, and you're set to turn heads wherever you go. Let's be real—nothing says "I'm here to slay" quite like a pair of boyfriend jeans.
$42.90
A pair of medium denim high-rise boyfriend jeans with trendy knee slits and multi-button closures.
$46.90
A pair of high-rise boyfriend jeans in denim with distressed accents and a cuffed 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: 9
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
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
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: XL
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: 11
Crush the day in stylish refresh high-rise wide-leg denim jeans. With a hip-hugging fit and wide-leg flare, these jeans bring effortless chic to your every move. Fit & FeaturesMedium-wash denim fabric, no stretch, High-rise waist, belt loops, Four-pocket styling, Front button and hidden zipper closure, Hip-hugging fit, Wide-leg flare silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Stylish Refresh High-Rise Wide-Leg Denim Jeans in Med Denim | Size: L
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
Elevate your style with totally edgy mid-rise wide-leg denim jeans. Featuring vintage vibes, a relaxed fit, and classic five-pocket design. Perfect for your effortlessly cool look. Fit & FeaturesVintage-inspired denim fabrication, no stretch, Mid-rise waist, Front button and hidden zipper closure, Five-pocket styling, belt loops, Relaxed wide-leg silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Totally Edgy Mid-Rise Wide-Leg Denim Jeans in Grey | Size: 9
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
Boyfriend Jeans
Step into the world of boyfriend jeans—the ultimate cool-girl staple that’s been rewriting the rules of denim for ages. There’s something about slipping into a pair of boyfriend jeans that just feels like you’re breaking all the right rules. Maybe it’s the way the relaxed fit sits low on your hips, giving you that effortless “I woke up like this” vibe, or maybe it’s the freedom to cuff, roll, and style them however your mood demands. Boyfriend jeans are the ride-or-die besties of your closet, ready to tag along for coffee runs, spontaneous road trips, or that last-minute invite to brunch. Whether you’re on the hunt for a boyfriend jeans sale to snag your next favorite pair or you’re eyeing boyfriend pants jeans for your bestie’s birthday (because, let’s be honest, who wouldn’t want to unwrap a little denim magic?), these jeans are the answer. They’re the go-to gift for the friend who’s always raiding your closet or the perfect treat-yourself moment when you need a little pick-me-up that’s as comfy as it is iconic.
When it comes to choosing your next pair of boyfriend jeans for sale, think about where you want to take them—and where you want them to take you. These jeans are all about versatility, so don’t be afraid to play with fit and wash. Go for a light, distressed wash if you’re channeling that off-duty model energy, or keep it classic with a clean, dark rinse that can swing from laid-back to semi-polished with a quick shoe swap. The beauty is in the details: look for subtle rips, frayed hems, or a perfectly slouchy silhouette that says, “I’m here for a good time, not a long time.” Boyfriend jeans are made for those moments when you want to feel comfy but still serve a look, whether you’re pairing them with a cropped tee for a chill hang or dressing them up with a blazer and heels for a night out where you’re the main character. And if you’re feeling extra daring, don’t sleep on mixing textures—throw on a leather jacket, a slinky cami, or even a pop of neon. These jeans are your blank canvas, and you’re the artist.
While boyfriend jeans are all about that borrowed-from-the-boys attitude, don’t forget to check out other trending styles that keep your denim game strong. If you’re vibing with the utility trend or just want to add a little edge to your wardrobe, slide over to our Cargo Jeans collection for more inspo. But no matter how you wear them, boyfriend jeans are the style secret every Windsor girl needs in her back pocket. They’re the jeans you reach for when you want to feel unstoppable, the ones that have your back from sunrise to after-hours adventures. So go ahead—rock them with sneakers, boots, or those strappy sandals you’ve been dying to show off. With boyfriend jeans, you’re not just wearing denim—you’re making memories, setting trends, and living life on your own terms.