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.
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RECOMMENDED
$9.97 $24.90 60% off
A taupe knit hoodie dress with a form-hugging fit and soft, stretchy ribbed fabric.
$42.90
A brown cropped denim shacket with long sleeves, button cuffs, and convenient flap pockets.
$6.97 $29.90 77% off
A black cotton-blend fleece pullover with moto graphics, ribbed hems, and a relaxed fit.
$49.90
A navy blue plaid woven shacket with a collared neckline and relaxed cropped fit.
$26.97 $58.90 54% off
A casual denim trucker jacket with a removable faux fur collar and cropped hem.
$34.90
A trendy black and white hoodie with a bubble crop hem and "New York" embroidered script.
$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.
$36.90
A black fishnet mesh bomber jacket with a zip-front and relaxed cropped fit for casual style.
$32.90
An oversized brown graphic tee with a mineral wash, featuring an eagle design and crew neckline.
$39.90
An oversized beige denim bomber jacket with relaxed long sleeves and a zip-up front closure.
$44.90
A cropped denim jacket with a relaxed silhouette, collared neckline, and buttoned chest pockets.
$24.90
A trendy oversized black tee featuring a bull rider graphic and western-inspired script.
$46.90 - $49.90
A chic olive cargo jogger with high-rise waist, metal ring trims, and elastic cuffed hems.
$49.90
A black faux leather and mesh jacket with illusion stripes, perfect for layering stylish outfits.
$16.90
A casual black crew neck crop top perfect for festivals and casual outings.
$9.97 $22.90 56% off
A black, form-hugging bodysuit with short sleeves and a thong bottom in soft knit fabric.
$46.90
A stylish pair of medium denim jeans with a high-rise waist and trendy knee destruction accents.
$12.97 $29.90 57% off
A stylish pair of black ribbed knit flare pants with a high-rise waist and flared hem.
$9.97 $39.90 75% off
A trendy black nylon puffer vest with a reversible design, zip front, and adjustable cropped hem.
$11.97 $28.90 59% off
A beige ribbed hacci knit top with an asymmetric off-shoulder neckline and long fitted sleeves.
$42.90
A stylish pair of charcoal high-rise cargo pants with adjustable hems and multiple pockets.
$28.90
A stylish sneaker in gold with faux suede contrast and a comfortable rubber gum sole.
$32.90
A chic black knit top with an asymmetric off-shoulder neckline and draped back design.
$34.90
A chic brown faux leather pant with a high-rise waist and flared hem for trendsetting style.
$46.90
An acid-wash black denim jacket with a cropped hem, standing collar, and front zipper closure.
$26.90
A white off-the-shoulder ribbed knit top with long fitted sleeves and a mid-length hem.
$42.90
A stylish denim jacket with a cropped elasticized hem, button cuffs, and flap pockets.
$49.90
A cognac satin jogger pant with a high-rise waist, cargo pockets, and adjustable drawcord cuffs.
$6.97 $22.90 70% off
A heather grey ribbed knit top featuring a V-neckline and stylish tie-front design.
$59.90
A stylish denim overall with a wide-leg silhouette, adjustable straps, and a cuffed hem.
$39.90
An ultra-cropped black acid wash denim jacket with button-down front and flap pockets.
$34.90
An ivory chenille knit hoodie with long fitted sleeves and a zippered front closure.
$46.90
A black knit midi sweater dress with abstract stripes, square neckline, and back slit accent.
$44.90
A light wash denim shrug jacket with relaxed long sleeves and an ultra-cropped hem.
$34.90
A comfy grey ribbed knit mid-rise flare pants perfect for post-pilates and casual outings.
$44.90
A trendy black acid wash denim shacket with a relaxed fit and button-down front.
$48.90
A high-rise medium denim cargo jean with flap pockets and a relaxed straight-leg silhouette.
$38.90
A sage ribbed knit midi dress with a V-neckline and form-hugging silhouette for casual chic style.
$34.90
A brown denim mini skort with a high-rise waist and dual front slits for a chic look.
$49.90
A trendy grey plaid shacket with a relaxed fit, perfect for layering during cozy season.
$36.90
A charcoal woven mini skort featuring a high-rise waist and pleated A-line overlay.
$42.90
A vintage-inspired grey denim with a mid-rise waist and relaxed wide-leg silhouette.
$32.90
A taupe ribbed knit pullover hoodie featuring a drawstring hood and tapered hems.
$9.97 $56.90 82% off
A camel faux wool trucker jacket featuring a sherpa collar and elastic cinched hems.
$9.97 $22.90 56% off
A heather grey off-shoulder crop top with fitted long sleeves and a form-hugging cotton-blend fabric.
$59.90
An oversized black faux leather blazer with a collared neckline and hidden side pockets.
$28.90
A stylish black faux leather sneaker featuring a striped pattern and comfortable footbed.
Now Trending
Layer on this cute crop denim shacket and watch your popularity soar! It features long sleeves with button cuffs and a collar neckline, button-down closures, flap pockets for convenience, and a flattering cropped hem. Complete the look in a trendy midi skirt for any casual plans! Fit & FeaturesTwill denim fabric, non-stretch, Long sleeves with button cuffs, Collar neckline, Button-down closure, Flap pockets, Cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Popular Cutie Long Sleeve Crop Denim Shacket in Brown | Size: XL
Flaunt your ice! This fab blazer features a stylish collared V-neckline and long sleeves with shoulder pads for added structure. The cropped hem is accented with a stunning rhinestone trim and swag chain, adding a touch of glamour to any outfit. Complete the look in statement denim jeans for dinner and drinks! Fit & FeaturesNon-stretch light wash denim fabric, Blazer style with collared V-neckline, Long sleeves with shoulder pads, Rhinestone trim and swag chain, Cropped hem, Runs true to size, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Oh So Icy Rhinestone Trim Crop Denim Blazer in Light Denim | Size: XL
Short, sweet, and exceptionally poised! This sleeveless button vest is everything for elevating your style. Pair with the matching shorts. Shop Matching Bottoms: Exceptional Poise High Rise Denim ShortsFit & FeaturesDark wash denim fabric with stretch, Crew neckline, Button-up front, Center split accent, Mid-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Exceptional Poise Sleeveless Button Denim Vest in Dark Denim | Size: L | Cotton
You'll always make a trendsetting impression in this denim shrug jacket! Perfect for layering over every cute 'fit, this jacket features relaxed long sleeves with button closures, a collar neckline and open front design, and an ultra-cropped hem that flaunts your figure. Complete the look in cute sandals. Fit & FeaturesLight wash denim fabric, no stretch, Collar neckline, Ultra cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Trendsetting Girlie Long Sleeve Denim Shrug Jacket | Size: XS
Get ready to turn some heads with your edgy arrival in this moto denim jacket! Featuring long sleeves with button cuffs and a standing collar neckline with button closure, this jacket adds an extra edge to any outfit. The front zipper closure and cropped hem with button strap add a unique style. Complete the look in booties. Fit & FeaturesAcid-wash denim fabric, Long sleeves with button cuffs, Standing collar neckline with button closure, Front zipper closure, Cropped length, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Edgy Arrival Moto Acid Wash Denim Jacket in Black | Size: L
Fit & FeaturesLeopard-printed denim fabric, Collared neckline, Chest pockets, Button-down closure, Long sleeves with single-button cuff, Oversized fit, Shop Matching Mini Skirt: Feeling Fierce Leopard Print Denim Mini Skirt Free Shipping on All Orders Over $75. | Windsor Feeling Fierce Leopard Print Denim Shacket | Size: S
Casual Trendsetter Faux Fur Denim Trucker Jacket
$26.97
$58.90
54% off
Fit & FeaturesDenim fabric, Collared neckline with removable faux fur trim, Long sleeves with single-button detail, Complete zip and button-down front, Chest pockets, Cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Casual Trendsetter Faux Fur Denim Trucker Jacket | Size: M
This trendy acid wash denim shacket needs to be included in your weekly rotation. Featuring a button-down front and relaxed fit, this cool shacket will be a new staple. Fit & FeaturesAcid wash denim fabric, no stretch, Collared neckline, Long sleeves with single-button detail, Chest pockets, Button-down front, Relaxed fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor New Staple Acid Wash Denim Shacket in Black Denim | Size: M
Any look you style with this sleeveless denim vest will instantly make it iconic! This vest is perfect for layering with a stylish V-neckline and front zip up closure. The flap pockets add functionality and the cropped length hem adds a modern touch. Complete the look in high-rise trouser pants for a chic style. Fit & FeaturesDenim fabric, slight stretch, V-neckline, Zip up front closure, Flap pockets, Cropped length, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Definite Icon Zip Up Pocket Denim Vest | Size: M
Looking to be an iconic cutie? Slip on this trucker denim jacket decorated with adorable bow embroidery and the perfect relaxed fit. Pair with sneakers. Fit & FeaturesLight wash denim fabric with bow embroidery, Long sleeves with button cuffs, Collared neckline, Front button-down closures, four front pockets, Relaxed fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Iconic Cutie Bow Trucker Denim Jacket in Light Denim | Size: M
Casual Streetwear
Picture this: you're stepping out onto the bustling streets, the city pulsing with life and energy, and you? You're rocking that effortless, head-turning vibe that only comes from nailing the perfect casual streetwear look. It's more than just clothing; it's an attitude, a lifestyle. It's about being unapologetically you, with a touch of edge and a whole lot of comfort. Whether you're grabbing coffee, hitting the skate park, or just lounging with friends, streetwear is your go-to style that never fails to express who you are.
For anyone looking to dive into the world of casual streetwear, or for those who are seasoned in this style game and want to elevate their wardrobe, there are a few key considerations. First, think about versatility. The best streetwear pieces are those that offer flexibility and can be mixed and matched to create a myriad of looks. Think hoodies, oversized tees, and joggers that can take you from day to night with just a change of accessories. Next, focus on comfort. Streetwear is rooted in cultures that value practicality and comfort, so opt for fabrics that let you move and groove without restrictions. Lastly, don't forget about your personal flair. Streetwear is inherently personal and reflective of individual style, so whether it’s through bold prints, striking colors, or unique cuts, make sure your choices speak to your personality.
Now, imagine gifting this freedom and style to someone special. Streetwear isn't just for the self-proclaimed fashionistas; it's for anyone who appreciates comfort, values practicality, and loves to express themselves through their attire. It's a thoughtful gift for the trendsetters, the artists, the dreamers, and the rebels in your life. As we transition from the crispness of winter into the bloom of spring, it’s the perfect time to refresh wardrobes with pieces that are as functional as they are fashionable. So, whether you’re looking to update your own collection or searching for the perfect gift, remember that the right streetwear can make anyone feel like they own the streets. For more inspiration on mastering this undeniably cool style, check out our selection of Trendy Casual Clothing and discover how to elevate your everyday look with a dash of urban flair.
With streetwear, every outfit is an opportunity to stand out and make a statement while keeping it all chill and laid-back. It's not just about looking good; it's about feeling good and making every pavement your runway. So, embrace the casual, the comfy, and the cool. After all, when it comes to streetwear, Windsor knows how to keep it trendy, fresh, and oh-so-wearable. Dive into our collection and find those key pieces that will define your street style this season. Remember, in the world of streetwear, there are no rules – just endless possibilities to express your unique self.