Medium Size Jackets
Ready to layer up and slay the day? Our collection of medium size jackets is here to elevate your style game with a splash of sass and a dash of daring. Whether you're strutting down the city streets or cozying up for a coffee date, these jackets are your go-to for that effortlessly chic vibe. Perfect for those in-between days when it's not too hot and not too cold, our medium size jackets are all about keeping you looking fabulous while feeling oh-so-comfortable. So go ahead, throw one on and let your inner fashionista shine!
$49.90
A black faux leather cropped jacket with an asymmetrical zipper and adjustable waist belt for edgy style.
$16.90
A black sheer mesh bolero with flared sleeves, perfect for prom or going out.
$49.90
A black faux leather biker jacket with zipper details and a cropped hem for an edgy look.
$69.90
A red faux leather moto jacket with long sleeves, zippered pockets, and a trendy striped pattern.
$46.90
An acid-wash black denim jacket with a cropped hem, standing collar, and front zipper closure.
$49.90
A leopard-printed denim shacket with an oversized fit, collared neckline, and chest pockets.
$42.90
A stylish denim jacket with a trucker silhouette, elasticized crop hem, and button-up front.
$44.90
A light denim cropped jacket with button cuffs, collar neckline, and functional front flap pockets.
$49.90
A black faux leather cropped moto jacket featuring a lapel collar, zippered front, and belted hem.
$36.90
A sleeveless denim vest with a V-neckline, zip closure, flap pockets, and a cropped hem.
$44.90
A sleek black faux leather cropped blazer with a relaxed fit and smooth woven lining.
$49.90
A camel faux suede crop jacket with long sleeves, button cuffs, and front pockets.
$29.90
A brown ribbed knit fitted hoodie with a drawstring hood and flattering seam detailing.
$45 $64.90 31% off
A sleek black faux leather bomber jacket with a trendy color block pattern and relaxed fit.
$49.90
A black twill woven crop jacket with cargo pockets and a relaxed fit for casual outings.
$24.90
A crepe long sleeve bolero in ivory that effortlessly elevates casual to dressy outfits.
$59.90
An edgy brown bomber jacket with distressed faux leather, rib knit details, and zippered pockets.
$49.90
A trendy grey plaid shacket with a relaxed fit, perfect for cozy layering and casual style.
$59.90
A black denim crop jacket with rhinestone lace-up plackets and button-down front for a glam touch.
$59.90
A charcoal faux leather bomber jacket with a cropped oversized fit and zipper front closure.
$46.90
A light denim cropped trucker jacket with a zip-up front and functional front pockets.
$44.90
A casually chic cropped denim jacket with a relaxed silhouette and buttoned chest pockets.
$59.90
A stylish ivory plaid shacket with knit lining, perfect for casual remote work settings.
$42.90
A taupe nylon hoodie bomber jacket with a relaxed fit and drawstring hood for casual style.
$35 $49.90 30% off
An effortlessly cute navy blue plaid shacket with a relaxed fit and dual chest pockets.
$59.90
An oversized denim cotton jacket featuring playful fringe trim, button-down front, and classic collar neckline.
$49.90
A black cotton-blend moto denim jacket with a lapel collar, zippered accents, and belted waist.
$59.90
A brown faux suede moto jacket with fringe detailing, perfect for festivals and Western adventures.
$49.90
A chic ivory faux leather jacket with striped sleeves, studded collar, and zippered pockets.
$49.90
A sleek black faux leather jacket with a collared neckline and zip-up front closure.
$49.90
A denim jacket with western-style stitching and a relaxed silhouette, perfect for festivals and concerts.
$44.90
A trendy denim moto jacket featuring a faded design, standing collar, and dual front pockets.
$49.90
A brown faux suede moto jacket with an asymmetric zip-front and belted waist for edgy style.
$46.90
A blue denim jacket featuring relaxed long sleeves, cropped hem, and classic button-up trucker style.
$39.90
A light denim cropped jacket featuring frayed edges, relaxed long sleeves, and front flap pockets.
$22.90
A sheer black mesh bolero with marabou feather-trimmed cuffs, fitted long sleeves, and an ultra-cropped hem.
$42.90
A brown cropped denim shacket with long sleeves, button cuffs, and convenient flap pockets.
$49.90
A navy blue plaid shacket with a relaxed fit, collared neckline, and cropped cinched hem.
$54.90
A chic oversized brown faux leather blazer with a lapel collar and single button closure.
$34.90
An oversized dark denim vest with large flap pockets and a trendy crop silhouette.
$42.90
A trendy white cropped denim jacket with a collared neckline and buttoned chest pockets.
$52.90
A trendy olive twill jacket with a fleece-lined hoodie, perfect for layering on chill nights.
$46.90
A light denim cropped jacket featuring a zip-up front, relaxed long sleeves, and statement flap pockets.
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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 a chic adjustable waist belt. Complete the look with a crop top and combat boots for major biker babe vibes. Fit & FeaturesAsymmetrical zippered front, Lapel collar, long sleeves, Zipper and snap button accents, Adjustable waist belt, Faux leather fabric with no stretch, Smooth lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Biker Chic Crop Jacket in Black | Size: L | Leather
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: S
Layer on this trucker denim jacket for good vibes and great times! With long sleeves and a collar neckline, this jacket offers a modern and edgy look. The zip-up front closure and front pockets provide functionality, while the cropped length adds a trendy touch. Complete the look in on-trend denim jeans. Fit & FeaturesLight wash denim fabric, Collar neckline, Zip-up front closure, Front pockets, Cropped length, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Good Vibes Zip-Up Crop Trucker Denim Jacket in Light Denim | Size: S
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: XL
Layer on this denim jacket featuring long sleeves with button cuffs and a collar neckline that keeps it classic. The front flap pockets and button up closures offer functionality while the cropped length hem keeps it trendy and perfect for styling with high-rise bottoms. Fit & FeaturesLight wash denim fabric, no stretch, Long sleeves with button cuffs, Collar neckline, Front flap pockets and button up closures, Cropped length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cute Classic Button Up Crop Denim Jacket in Light Denim | Size: S
The faux leather cropped moto jacket features a lapel collar, a zippered front closure, long sleeves with a buckled cuff accent, and a belted cropped hem with a double buckle design. Complete look with high waist jeans. Fit & FeaturesFaux leather fabric with woven lining, no stretch, Lapel collar, Zipper front closure, Long sleeves, buttoned shoulder straps, buckle cuff accent, Belted cropped hem, double buckle design, Relaxed fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Untamed Chic Faux Leather Cropped Moto Jacket in Black | Size: L
From errands and outings, this denim cropped jacket will have you looking trendy everywhere you go! Fit & FeaturesAcid wash denim fabric, Long sleeves with button cuffs, Collared neckline, Button-down front closures, Front flap pockets, Ultra cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Trend Always Acid Wash Crop Denim Jacket in Black | Size: S
Layer this faux suede crop jacket for the perfect finishing touch as you head out the door! Fit & FeaturesSoft faux suede fabric, minimal stretch, Long sleeves, button cuffs, Collared neckline, Button-down front, Front buttoned chest pockets, Cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Ready To Go Faux Suede Crop Jacket in Camel | Size: M
It's in your nature to be trendy and this woven jacket is no exception! Made from twill woven fabric, this relaxed-fitting crop jacket brings a classic utility vibe with long sleeves, a collar neckline, and cargo pockets with pull strap closures to keep your loose items secure. Complete the look in best-selling bottoms for a day or night outing! Fit & FeaturesNon-stretch twill woven fabric, Cargo pockets with pull strap closures, Front button closures, Long sleeves with button closures, Cropped hem, Relaxed fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Trendy Nature Cargo Woven Crop Jacket in Black | Size: M | Woven Fabric
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 Pink | Size: S | Knit Fabric
Medium Size Jackets
Medium size jackets are the unsung heroes of your closet—always ready to step up when the weather wants to keep you guessing. They’re that perfect in-between layer: not too bulky to weigh you down, not too skimpy to leave you shivering. Whether you’re running errands, heading out for a spontaneous road trip with your besties, or just need something to toss over your shoulders for a late-night coffee run, a medium jacket is your go-to move. Picture yourself breezing into a rooftop get-together, the city lights twinkling below, your confidence on full blast thanks to that just-right layer hugging your frame. That’s the magic of a great medium size jacket: it’s got your back, literally and figuratively, and gives you the freedom to own every moment without worrying about the weather or your look. If you’re the type who likes to keep your options open—maybe you want to cinch it at the waist for a little shape, or leave it open and breezy for that effortless “I woke up like this” vibe—medium jackets are all about versatility. They’re the ride-or-die piece that makes your wardrobe work harder, letting you mix and match with everything from curve-hugging mini dresses to lived-in denim and sneakers.
Gifting a medium size jacket? You’re basically handing over a ticket to instant cool, and trust us, your friends or fam will be obsessed. These jackets are the ultimate “I saw this and thought of you” gift, perfect for the friend who’s always cold in restaurants, the sibling who’s impossible to shop for, or even your mom who deserves to feel like the main character. They’re also the ultimate travel buddy—easy to pack, throw on, and style up or down, no matter where the adventure leads. When you choose a windsor jacket, you’re picking more than just a layer; you’re choosing a vibe, a mood, and a little extra confidence boost for every plan in your calendar. Medium jackets are designed with real life in mind—think roomy enough for a cozy sweater underneath, but tailored enough to keep your silhouette on point for those impromptu mirror selfies. Plus, with smart details like adjustable cuffs, sleek zippers, and pockets for days, you’ll never have to sacrifice style for function. If you’re looking to expand your jacket game and want something a little lighter, don’t miss our curated edit of Lightweight Jackets for those days when you just need a hint of coverage.
There’s something about slipping into a windsor jacket that just hits different. Maybe it’s the way it instantly pulls your whole look together, or maybe it’s the subtle confidence boost you get knowing you’re ready for whatever the day (or night) throws your way. Medium size jackets are the MVPs for unpredictable weather, spontaneous plans, and those “should I bring a jacket?” moments that always pop up. They’re made for the girl who’s always on the move, who wants to look put-together without feeling overdone, and who knows the power of a killer outer layer. When you’re building your collection, think about what matters most to you—maybe it’s a bold pop of color, a classic silhouette, or details that make your jacket feel one-of-a-kind. Whatever your style, medium jackets are all about celebrating your individuality and making every outfit a little more “you.” So go ahead, claim your space, turn heads, and let your jacket do the talking. With Windsor, you’re never just wearing a jacket—you’re making a statement, and the world is your runway.