Streetwear Jackets

Streetwear jackets are the ultimate flex for every Windsor girl who lives for turning sidewalks into runways. Whether you’re layering up for a late-night adventure or just want to give your ‘fit that extra edge, these bold pieces have your back. From spontaneous coffee runs to impromptu photo ops, your streetwear jacket is your ticket to instant cool-girl status. Ready to serve looks and break hearts? Let’s get you dripped out and unstoppable.

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Windsor Biker Chic Crop Jacket in Black

$49.90

A black faux leather cropped jacket with an asymmetrical zipper and adjustable waist belt for edgy style.

Ride In Style Faux Leather Moto Crop Jacket in Red

Ride In Style Faux Leather Moto Crop Jacket in Red

$69.90

A red faux leather moto jacket with long sleeves, zippered pockets, and a trendy striped pattern.

Windsor Edgy Arrival Moto Acid Wash Denim Jacket in Black

$46.90

An acid-wash black denim jacket with a standing collar and cropped hem for an edgy look.

Windsor Trendy Arrival Denim Moto Jacket

$44.90

A trendy denim moto jacket featuring a faded design, standing collar, and dual front pockets.

On My Way Trucker Crop Denim Jacket

$42.90

A stylish denim jacket with a cropped elasticized hem, button cuffs, and flap pockets.

Shift Into Glam Faux Leather Moto Jacket in Black

$64.90

A black faux leather moto jacket with an asymmetrical zipper and adjustable waist belt.

Casual Cool Vibes Hoodie Bomber Jacket in Taupe

$42.90

A taupe nylon hoodie bomber jacket with a relaxed fit and drawstring hood for casual wear.

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Biker Chic Crop Jacket in Black

$49.90

(52)

Change gears in a cropped jacket and add a little biker chic-ness to your look! Create an edgy look in this biker moto jacket that features an asymmetrical zipper front with a lapel collar, snap button accents, and an adjustable waist belt. Fit & FeaturesFaux leather fabric with no stretch, smooth lining, Lapel collar, asymmetrical zippered front, Long sleeves with zippered accents, Zipper and snap button accents, Adjustable waist belt, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Biker Chic Crop Jacket in Black | Size: XL | Leather

Scene Stealer Faux Fur Crop Denim Jacket

$49.90

(11)

Serving vintage glam with a rockstar twist. This faux fur trim denim jacket is oversized, plush, and impossible to ignore—the perfect throw-on for concerts, nights out, or everyday styling. Fit & FeaturesDenim fabric, sewn-in knit lining, Faux fur trim collared neckline, Long sleeves, faux fur trim cuffs, Cropped-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Scene Stealer Faux Fur Crop Denim Jacket | Size: M | Knit Fabric

Ride In Style Faux Leather Moto Crop Jacket in Red

$69.90

(8)

Wherever you're headed, arrive in style! This faux leather moto jacket features long sleeves, a mock neckline with snap-button closure, front zipper closure, zippered pockets for keeping your hands warm, a cropped hem, and a trendy contrast striped pattern for added flair. Complete the look in a tee and slit midi skirt for a cute-edgy vibe! Fit & FeaturesLong sleeves, Mock neckline with snap-button closure, Front zipper closure, zippered pockets, Cropped hem, Contrast striped pattern, Faux leather fabric, sewn-in woven lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Ride In Style Faux Leather Moto Crop Jacket in Red | Size: M

Frost Mode Faux Fur Crop Jacket in Fuchsia

$59.90

(7)

Plush, polished, and made to flex. This zip-up faux fur crop jacket brings cozy luxury to your cold-weather lineup—soft to the touch, cropped to perfection, and ready to elevate every winter fit. Fit & FeaturesPlush faux fur fabric, sewn-in woven lining, Collar neckline, Front zip-up closure, Long sleeves, Crop-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Frost Mode Faux Fur Crop Jacket in Fuchsia | Size: S

Street Cue Crop Denim Bomber Jacket in Brown

$54.90

(4)

Off-duty but still on. This cropped denim bomber jacket adds instant cool style to anything you throw it over—because basics deserve better. Fit & FeaturesCotton denim fabric, no stretch, Standing collar neckline, Front hidden zip-up closure, snap-button closures, Front flap pockets, Elasticized cropped-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Street Cue Crop Denim Bomber Jacket in Brown | Size: XL | Cotton

Life In The Fast Lane Crop Moto Jacket in Brown

$69.90

(4)

Experience life in the fast lane in this sleek moto jacket with a bold colorblock design and cropped fit. It’s the perfect jacket to layer over any outfit for a day or night out. Fit & FeaturesFaux leather fabric, color block design, sewn-in woven lining, Standing collar neckline with button closure, Long sleeves, Side zippered pockets, Cropped-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Life In The Fast Lane Crop Moto Jacket in Brown | Size: M | Leather

On My Way Trucker Crop Denim Jacket

$42.90

(3)

Layer on this trucker crop denim jacket on your way out looking fresh. This jacket features long sleeves with button cuffs for versatile styling, a collar neckline for a polished look, and convenient flap pockets. The elasticized crop hem and trucker silhouette add modern flair to the classic denim fabric. Complete the look in a trendy denim midi skirt for a cute fit! Fit & FeaturesDenim fabric, no stretch, Button up front closures, Flap faux pockets, Elasticized crop hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor On My Way Trucker Crop Denim Jacket | Size: M

At Your Leisure Zip-Up Crop Jacket in Chartreuse

$29.90

(1)

A comfy and cute zip-up crop jacket perfect for post-pilates and grabbing coffee! Pair with the matching bottoms. Fit & FeaturesStretchy rib knit fabric, Fitted long sleeves, Mock neckline, Zip-up front closure, Fitted crop hem, Runs true to size, Shop The Matching Pants: At Your Leisure Mid-Rise Flare Pants Free Shipping on All Orders Over $75. | Windsor At Your Leisure Zip-Up Crop Jacket in Chartreuse | Size: S | Knit Fabric

Polished Edge Crop Bouclé Jacket in Black-2

$59.90

(1)

This bouclé lurex crop jacket serves polished-but-playful energy — sparkly woven texture, gold button details, and a flirty crop length that ties the whole “effortlessly chic” vibe together. It’s giving a holiday party, a gallery opening, and any night you want to look expensive without even trying. Shop The Matching Skort: Polished Edge Ruffle Bouclé SkortFit & FeaturesBouclé lurex woven fabrication, sewn-in lining, Collar neckline, Long sleeves, structured shoulders, Decorative button and pocket detailing, Crop-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Polished Edge Crop Bouclé Jacket in Black-2 | Size: M | Woven Fabric

Cropped Attitude Faux Leather Jacket in Black

$49.90

(1)

From coffee runs to late nights, this faux leather jacket nails that effortless cool-girl vibe in the city! Fit & FeaturesFaux leather fabric, sewn-in woven lining, Long sleeves, Collar neckline, Front zip-up closure, Front pockets, Cropped-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cropped Attitude Faux Leather Jacket in Black | Size: S

Streetwear Jackets

When it comes to leveling up your cold-weather rotation, nothing hits quite like a streetwear jacket. These aren’t just any jackets—they’re the statement-makers that instantly pull a look together, whether you’re layering up for a late-night city stroll, heading out to a concert, or just running errands with an edge. Streetwear jackets are all about that blend of comfort, attitude, and versatility. Think oversized bombers with bold graphics, faux fur lined acid wash bomber jackets that channel major Y2K nostalgia, and denim truckers with that perfectly distressed finish. There’s a certain energy to cool streetwear jackets—the kind that makes you want to throw one on over literally anything and suddenly feel like you’ve got your whole vibe figured out. Even as the temps drop in December, these jackets are built for more than just warmth. It’s about the oversized fits, the unexpected color-blocking, the patchwork details, and those extra-deep pockets (because who actually wants to carry a bag everywhere?). Whether you’re into moto-inspired silhouettes for that touch of rebellion, varsity styles for a hint of vintage athletic flair, or puffer jackets that keep you toasty without sacrificing style, there’s a streetwear jacket for every mood, every plan, and every playlist.

If you’re shopping for yourself, the right street wear jacket is a wardrobe MVP—easy to throw on over a hoodie for a quick coffee run or layered with a turtleneck and wide-leg jeans for a night out. But these jackets also make seriously solid gifts. They’re the kind of piece your best friend will wear on repeat, the sibling who’s always cold will finally stop “borrowing,” or the cousin who lives for limited drops will appreciate for its on-trend details. Streetwear jackets work for anyone who wants to add some personality to their outerwear game, and they’re perfect for gifting because they’re inherently forgiving in fit and full of personality. Look for features like soft linings, water-repellent fabrics, or convertible hoods if you want to score extra points for practicality. And don’t sleep on the details—embroidered patches, contrast stitching, and unique washes are what take these jackets from basic to next-level. If you’re feeling overwhelmed by all the choices, start with what feels most like you (or the person you’re shopping for). Maybe it’s an oversized puffer with a graphic print, or maybe it’s a classic acid wash denim with a faux fur collar that goes with everything. Either way, a streetwear jacket is a shortcut to feeling pulled-together, even on days when you’re just throwing on leggings and sneakers.

Streetwear jackets are built to flex with your lifestyle, whether you’re headed to class, hopping between holiday parties, or just want to make your everyday walks a little more interesting. They’re the ultimate in wearable self-expression—part comfort, part confidence boost, and always ready for a photo op. The best part? You don’t have to break the bank to find a jacket that looks and feels amazing. Focus on details that matter to you: oversized hoods for extra coziness, bold graphics for standing out, or vintage-inspired patchwork for that throwback vibe. And if you’re looking to round out your outerwear collection or need a little more inspiration, check out our Popular Jackets page for even more styles that are trending right now. Whether you’re gifting or getting, these jackets are the kind of pieces you’ll reach for all season long—and probably every season after that.

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