Hipster Jeans

Dive into the effortlessly cool world of hipster jeans, where vintage vibes meet modern flair and every pair is a statement of individuality. These jeans are your ticket to owning that laid-back, effortlessly chic aesthetic that screams originality. Whether you're hitting up a local coffee shop or exploring the city streets, hipster jeans have got you covered with their perfect balance of comfort and style. So go ahead, channel your inner trendsetter and let your denim do the talking. After all, in a world full of basics, be a classic!

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Windsor High-Rise Distressed Boyfriend Jeans in Medium Denim

$42.90

A pair of medium denim high-rise boyfriend jeans with trendy knee slits and multi-button closures.

Currently Trending Low-Rise Denim Jeans in Med Denim

$49.90

A pair of medium denim low-rise jeans featuring a relaxed baggy fit and classic five-pocket styling.

Make A Scene Mid-Rise Flare Denim Jeans in Dark Denim

$49.90

A pair of dark denim mid-rise flare jeans with seam detailing and a hip-hugging fit.

Windsor High-Rise Distressed Mom Skinny Jeans in Medium Denim

$42.90

A stylish pair of medium denim high-rise mom jeans with distressed knee details and a skinny fit.

Cool Captured High Rise Cargo Denim Jeans in Black

Best Seller

Cool Captured High Rise Cargo Denim Jeans in Black

$49.90

A stylish pair of black high-rise cargo denim jeans with a straight-leg silhouette and flap pockets.

Best Seller

Off The Radar Camouflage Straight Leg Denim Jeans in Grey

$49.90

A stylish pair of grey camouflage denim jeans featuring a low-rise waist and convenient cargo pockets.

Windsor Prepare To Love High RIse Boyfriend Denim Jeans

$46.90

A high-rise boyfriend jean in vintage-inspired denim with distressed accents and a cuffed hem.

Windsor So Obsessed Rhinestone Cutout Straight Leg Denim Jeans in Black

$59.90

A pair of black high-rise straight leg jeans featuring rhinestone cutout trim and a heart-shaped bum seam.

Cutie In Cargo High-Rise Denim Jeans

$49.90

A stylish pair of high-rise denim cargo jeans featuring a straight-leg silhouette and eight-pocket design.

Sculpt And Serve High-Rise Skinny Denim Jeans in Light Denim

$42.90

A pair of light denim high-rise skinny jeans crafted from premium non-stretch fabric with classic five-pocket styling.

Windsor Bold High-Rise Acid Wash Cargo Jeans in Black

$44.90

A stylish pair of black high-rise acid wash cargo jeans with a slight stretch and cargo pockets.

Street Style Straight-Leg Cargo Denim Jeans in Med Denim

$46.90

A pair of medium denim cotton-blend jeans with a mid-rise waist and straight-leg cargo silhouette.

Now Trending

Windsor High-Rise Distressed Boyfriend Jeans in Medium Denim

$42.90

(77)

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: 7

Windsor High-Rise Distressed Mom Skinny Jeans in Medium Denim

$42.90

(28)

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: 13

Windsor Cool Captured High Rise Cargo Denim Jeans in Black

$49.90

(19)

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

Off The Radar Camouflage Straight Leg Denim Jeans in Grey

$49.90

(18)

It'll be hard for people not to notice you in these cool camouflage denim jeans with an on-trend mid-rise waist and convenient cargo pockets. Fit & FeaturesCamouflage print, denim fabric, no stretch, Mid-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: L

Make A Scene Mid-Rise Flare Denim Jeans in Dark Denim

$49.90

(8)

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

Prepare To Love High RIse Boyfriend Denim Jeans

$46.90

(6)

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: 9

Windsor So Obsessed Rhinestone Cutout Straight Leg Denim Jeans in Black

$59.90

(4)

Add a touch of shine to your denim drawer with these high-rise straight leg jeans boasting rhinestone trim cutouts and a flattering heart-shaped bum seam! Fit & FeaturesDenim fabric, minimal stretch, High-rise waist, Front rhinestone trim cutouts, Straight-leg fit, heart-shaped bum seam, Front button and hidden zipper closure, Four-pocket styling, belt loop accents, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Obsessed Rhinestone Cutout Straight Leg Denim Jeans in Black | Size: M

Cutie In Cargo High-Rise Denim Jeans

$49.90

(4)

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: XS

Windsor Catch Me In Cargo Mid-Rise Straight-Leg Jeans in Beige

$49.90

(4)

Lowkey utility, highkey cool. These cargos are made for off-duty days, casual hangs, or whenever you want your outfit to say “I got this” without trying. Fit & FeaturesDenim fabric, slight stretch, Mid-rise waist, Straight-leg relaxed fit, Side cargo flap pockets, Front button and hidden zipper closure, belt loops, Five-pocket styling, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Catch Me In Cargo Mid-Rise Straight-Leg Jeans in Beige | Size: L

Windsor Sculpt And Serve High-Rise Skinny Denim Jeans in Light Denim

$42.90

(2)

These denim jeans understood the assignment. With a flattering high-rise waist and sculpting skinny leg, they’re your new go-to for that clean-girl-everyday vibe. Fit & FeaturesPremium non-stretch light wash denim fabric, High-rise waist, Skinny, sculpted leg fit, Front button and hidden zipper closure, Five-pocket styling, belt loop accents, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sculpt And Serve High-Rise Skinny Denim Jeans in Light Denim | Size: 7

Hipster Jeans

Let’s be honest—jeans are never just jeans. They’re an attitude, a time capsule, a mood, and sometimes, a full-on identity shift. Enter hipster jeans: the denim that doesn’t just keep up with trends but rewrites them. With their signature low-rise fit and a silhouette that’s equal parts retro and rebellious, hipster jeans have officially made their comeback, and this time, they’re bringing the whole crew—think baggy low-rise, classic hip-huggers, straight legs with Y2K energy, and bootcuts that practically beg for a platform shoe. If you’ve ever stood in front of your closet, torn between wanting to look effortlessly cool and actually feeling comfortable, these are the pairs that make the decision for you. They sit on your hips just right, give off that “I thrifted this in Brooklyn” vibe, and work with pretty much everything you already own. Whether you’re layering up for crisp November days with chunky knits and vintage tees, or leaning into the nostalgia with a cropped cardigan and a bucket hat, hipster denim is all about making the old-school new again—without ever looking like you tried too hard. The best part? They’re a style chameleon. Dress them up with a slinky cami and leather jacket for a night out, or keep it low-key with sneakers and a graphic tee for coffee runs and record store browsing. If you’re on the hunt for what to wear with hipster jeans, the answer is: whatever feels like you, but cooler.

Skinny jeans hipster styles are having a moment, too—proving that “hipster” isn’t just about baggy silhouettes or ironic prints. It’s about attitude, and the confidence to remix your wardrobe staples in a way that feels totally your own. Maybe you’re gifting a pair to your trendsetting bestie who already has a collection of vintage band tees, or maybe you’re treating yourself to a fresh fit for Friendsgiving and all those “just one more photo” moments. Hipster jeans are made for sharing, borrowing, and swapping—because let’s face it, the best denim stories always come with a side of “remember when?” They’re also a game-changer for anyone looking to break out of a style rut without blowing their budget. If you’re new to the world of hipster denim, start with a classic low-rise flare or a relaxed straight leg. These shapes are universally flattering, easy to style, and give you that instant “I know what I’m doing” energy—even if you’re just winging it. And if you’re feeling bold, go for a baggy low-rise or bootcut with a raw hem. Pair them with a fitted turtleneck and lug-sole boots, or layer on oversized outerwear for a vibe that’s equal parts cozy and cool. Don’t be afraid to experiment—this is the season for mixing, matching, and making your own rules. And if you’re ready to explore more fresh takes on denim, check out our full lineup of Modern Jeans for even more inspo.

When it comes to hipster jeans, the details matter—think vintage-inspired washes, unexpected distressing, and hardware that catches the light just so. These aren’t your basic blues; they’re statement-makers that play well with every layer in your closet. If you’re shopping for yourself, look for fits that hug your hips without pinching and fabrics that move with you, not against you. If you’re gifting, pay attention to personal style cues: someone who lives in combat boots and oversized sweaters will love a baggy low-rise, while a friend who’s all about sleek lines and minimalist accessories might gravitate toward a skinny jeans hipster look. Hipster jeans are the answer to chilly morning commutes, impromptu road trips, and every “what do I wear?” text in your group chat. They’re a little bit nostalgic, a little bit rebellious, and totally ready for whatever the season throws your way. Whether you’re curating your closet for fall or shopping for someone who deserves a style upgrade, hipster denim is the move—versatile, affordable, and always a conversation starter.

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