Casual Streetwear
Hey there, street style stunner! Time to own the sidewalk with our fab collection of casual streetwear that screams effortlessly cool and undeniably chic. Whether you're strutting down city blocks or just hanging out with your crew, these looks are all about comfort meeting killer style. Think laid-back vibes with a splash of edge—perfect for those who live life on their own terms. So go ahead, mix and match your faves, and let your wardrobe do the talking as you turn every street into your personal runway.
$49.90
A pair of black high-rise cargo denim jeans with a straight-leg silhouette and trendy flap pockets.
$46.90
A pair of medium denim cotton-blend jeans with a mid-rise waist and straight-leg cargo silhouette.
$49.90
A navy blue plaid woven shacket with a collared neckline and relaxed cropped fit.
$59.90
A charcoal faux leather bomber jacket with a cropped oversized fit and zipper front closure.
$42.90
A taupe nylon hoodie bomber jacket with a relaxed fit and drawstring hood for casual style.
$46.90 - $49.90
A chic olive cargo jogger with high-rise waist, metal ring trims, and elastic cuffed hems.
$49.90
A trendy pair of grey camouflage denim jeans featuring a low-rise waist and practical cargo pockets.
$42.90
A stylish pair of brown high-rise cargo pants with adjustable drawcord hem and multiple pockets.
$46.90
An acid-wash black denim jacket with a cropped hem, standing collar, and front zipper closure.
$34.90
A brown denim mini skort with a high-rise waist and dual front slits for a chic look.
$39.90
A green scuba knit crop hoodie jacket with pockets, relaxed sleeves, and a front zipper closure.
$36.90
A trendy dark denim halter crop top with a zip-front and form-hugging fit for festivals.
$49.90
A dark denim jean with a mid-rise waist, flare hem, and multiple cargo-inspired pockets.
$32.90
A pair of dark denim mid-rise shorts with a vintage-inspired fabric and edgy frayed hem.
$9.97 $29.90 67% off
A brown high-rise knit flare pant with a fold-over waist and ribbed hacci fabric for comfort.
$42.90
A trendy cropped denim jacket with a collared neckline, button-down front, and fitted silhouette.
$36.90
A dark denim mini skort featuring a high-rise fit, faux wrap overlay, side tie, and frayed hem.
$32.90
A trendy pair of grey mid-rise denim shorts featuring an acid wash design and form-hugging fit.
$49.90
A trendy grey plaid shacket with a relaxed fit, perfect for layering during cozy season.
$44.90
A trendy denim moto jacket featuring a cool faded design and a fitted cropped hem.
$36.90
An edgy black acid-wash denim skort with a mini-length overlay and hidden shorts for coverage.
$12.90
A black ribbed knit bandeau top with a strapless neckline and form-hugging fit.
$34.90
An oversized crop denim vest in dark denim with large flap pockets and button-down front closures.
$6.97 $29.90 77% off
A taupe ribbed knit bodycon mini dress with spaghetti straps and a scoop neckline for casual outings.
$54.90
A chic oversized brown faux leather blazer with a lapel collar and single button closure.
$49.90
A pair of dark denim straight-leg jeans featuring a mid-rise waist and stylish lace-up design.
$9.97 $42.90 77% off
A high-rise denim skater skort with a contrast tie-front waistband, pleating, and hidden fitted shorts.
$52.90
A trendy olive twill jacket with a fleece-lined hoodie, perfect for layering on chill nights.
$32.90
A relaxed off-white linen-blend crop top featuring a collared neckline and button-down front.
$49.90
A pair of medium denim low-rise jeans with a relaxed baggy fit and classic five-pocket styling.
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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: XL
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: XS
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 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: 13
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: M
Your best fit yet will always feature these high-rise bootcut denim jeans perfect for casual slays. Fit & FeaturesDark wash denim fabric, slight stretch, High-rise waist, front button and hidden zipper closure, Hip-hugging slim fit, Bootcut silhouette, Slight flare hem, Five-pocket styling, belt loop accents, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Far So Good High-Rise Bootcut Denim Jeans in Dark Denim | Size: L
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
These mid-rise flare denim jeans bring effortless edge with cargo pockets and a sleek fit that works from coffee runs to concert nights! Fit & FeaturesDark wash denim fabric, Mid-rise waist, Hip-hugging fit, Flare hem, Cargo front pockets, hip front pockets, and back pockets, Front button closure, belt loop closures, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cool Girl Cargo Mid Rise Flare Denim Jeans in Dark Denim | Size: XS
Casual Streetwear
When it comes to nailing that off-duty look, nothing hits quite like casual streetwear. It’s the ultimate vibe for the girl who’s got a million things on her calendar but still wants to look like she just stepped out of a style mood board. Whether you’re running errands, catching up with your crew at your favorite coffee spot, or just living your best life, streetwear Windsor style is all about blending comfort with a hit of attitude. You know that feeling when you toss on something oversized and instantly feel like you could run the world? That’s the magic of casual streetwear women love—it’s fashion that says, “I woke up like this,” but with a wink, because you know every detail was chosen with intention. From chill joggers to graphic tees and the kind of jackets that make you want to strut, these pieces are designed to move with you, keeping it cute and effortless from sunrise to after-hours adventures.
Gifting casual streetwear is basically like handing someone a ticket to confidence. It’s perfect for the friend who’s always first in the group chat with the fit check, the sister who lives for TikTok OOTDs, or the cousin who’s about to start college and needs that “main character” energy. And honestly, it’s a little treat for yourself, too, because sometimes you need to reward your own hustle. Think of those moments when you’re lounging at home, but then plans pop up out of nowhere—streetwear has your back. It’s the sweet spot between cozy and cool, making it easy to transition from Netflix marathons to spontaneous road trips. Plus, these pieces are made to be mixed, matched, and lived in, so you can serve a fresh look every single day without breaking a sweat. If you’re looking to amp up your wardrobe with pieces that are as versatile as your schedule, you’ll find endless inspo in our curated collection of Trendy Casual Clothing.
In the world of streetwear Windsor, the rules are simple: wear what makes you feel unstoppable. Style isn’t about blending in—it’s about owning your story, whether you’re layering up for a night out or keeping it low-key for a day of exploring the city. Casual streetwear women gravitate toward is all about self-expression, so don’t be afraid to play with bold prints, unexpected textures, or those statement accessories that make your heart skip a beat. The best part? These looks are built for real life, so you can chase your dreams, break a few rules, and look absolutely iconic doing it. So go ahead—turn the sidewalk into your runway and let your outfit do all the talking. Your next favorite look is just waiting to be discovered, and trust us: the world is your stage.