Oversized Outerwear
Oversized outerwear is your ticket to effortless chic and ultimate comfort, darling! Whether you're strutting down the city streets or cozying up for a laid-back brunch with your squad, these statement pieces are all about making waves while keeping things snug. Think of them as your stylish armor against the chill, wrapping you in layers of confidence and cool-girl vibes. From bold patterns to classic neutrals, oversized outerwear lets you play with proportions and express your unique style, turning every sidewalk into your personal runway. So go ahead, embrace the drama and let your outerwear do the talking!
$29.90
A red oversized knit sweater bolero with slouchy sleeves and an ultra-cropped hem.
$74.90
A charcoal faux leather bomber jacket with washed seams and an oversized, vintage chic fit.
$49.90
A leopard-printed denim shacket with an oversized fit, collared neckline, and chest pockets.
$59.90
A brown plaid oversized shacket in faux wool with faux suede lining and chest pockets.
$49.90
A trendy grey plaid shacket with a relaxed fit, perfect for layering during cozy season.
$59.90
An oversized ivory faux leather moto jacket with belted accents and a chic cropped hem.
$34.90
An oversized crop denim vest in dark denim with large flap pockets and button-down front closures.
$14.97 $34.90 57% off
An oversized navy blue sweatshirt with a cozy fleece lining and stylish graphic design.
$59.90
An ivory plaid oversized shacket with a collared neckline, perfect for casual virtual gatherings.
$16.97 $39.90 57% off
An oversized charcoal crop hoodie with soft fleece lining and "Los Angeles" front graphic.
$54.90
A chic oversized brown faux leather blazer with a lapel collar and single button closure.
$59.90
A charcoal faux leather bomber jacket with a cropped oversized fit and zipper front closure.
$59.90
An oversized denim cotton jacket featuring playful fringe trim and classic button-down front closures.
$26.90
An ivory faux fur shawl with a satin-like lining and optional hook-eye closure.
$79.90
A brown faux leather trench coat featuring a belted waist, double-breasted closure, and long sleeves.
$49.90
A navy blue plaid shacket with a relaxed fit, collared neckline, and cropped cinched hem.
$59.90
An edgy brown bomber jacket with distressed faux leather and rib knit details for a vintage look.
$59.90
A black woven duster trench coat with a belted waist and hidden side pockets.
$42.90
A taupe nylon hoodie bomber jacket with a relaxed fit and drawstring hood for casual wear.
$34.90
A dreamy ivory crochet lace kimono with a relaxed fit and half-length loose sleeves.
$35 $49.90 30% off
An effortlessly cute navy blue plaid shacket with a relaxed fit and dual chest pockets.
$52.90
A trendy olive twill jacket with a fleece-lined hoodie, perfect for layering on chill nights.
$59.90
A stylish ivory plaid shacket with knit lining and button-down front, perfect for casual occasions.
$52.90
A beige woven sleeveless long vest featuring a lapel collar, belted waist, and side pockets.
Now Trending
Layer on this trendy plaid shacket perfect for cozy season featuring a collared neckline, long sleeves with buttons to cuff, a complete button-down front, chest pockets, and a casually chic relaxed fit. Style with jeans and booties. Fit & FeaturesWoven fabric with buffalo plaid print, no stretch, Collared neckline, Long sleeves with single-button detail, Button-down front, Dual flap chest pockets, Long-length hem, relaxed fit, 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 Cozy Season Plaid Button-Down Shacket in Grey | Size: S | Woven Fabric
It's the season for this plaid oversized shacket to come out and play! Keep cozy and cute in this shacket perfect for styling with boots. Fit & FeaturesFaux wool fabrication, faux suede lining, no stretch, Plaid pattern, Collared neckline, Long sleeves with single button cuff, Button-down front, Chest pockets with buttoned flap closure, Oversized fit, 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 Plaid Passion Oversized Faux Wool Shacket in Brown | Size: S/M | Faux Suede
Casually cozy, this plaid woven shacket features a collared neckline, long sleeves, a button-down front with buttoned chest pockets, and a cropped cinched hem with an overall relaxed fit. Layer over a basic top with a denim skirt and booties! Fit & FeaturesPlaid woven fabric, no stretch, Collared neckline, Long sleeves with single-button detail, Button-down front, Dual buttoned chest pockets, Cropped hem, elastic cinched back hem, relaxed fit, 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 Casually Cozy Plaid Woven Cropped Shacket in Navy Blue | Size: M | Woven Fabric
Forever femme with endless styling options, this sheer lace long sleeve topper elevates your day-to-night look. Fit & FeaturesSheer lace fabric, moderate stretch, Fitted long sleeves, Crew neckline, Ultra-cropped length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Forever Femme Sheer Lace Long Sleeve Topper in Black | Size: S | Lace Fabric/Sheer Lace Fabric
Fit & FeaturesPlaid printed woven fabric with lining, Collared neckline, Long sleeves with single-button detail, Complete button-down front, Chest pocket, Oversized fit, 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 Comfy Trend Plaid Woven Oversized Shacket in Ivory | Size: S | Woven Fabric
Effortless Cutie Long Sleeve Plaid Shacket in Navy Blue
$35 $49.90
30% off
Layer on this effortlessly cute long sleeve plaid shacket perfect for pairing with a fitted top and denim jeans for everyday styling. Fit & FeaturesPlaid printed faux wool fabric, no stretch, Collared neckline, Button down front, Long sleeves with single-button detail, Dual chest pockets, Relaxed fit, 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 Effortless Cutie Long Sleeve Plaid Shacket in Navy Blue | Size: S
Get comfy in the cozy layer plaid woven shacket! With a relaxed fit, button-down front, and chic plaid pattern, it's perfect for casual hangouts. Total vibe! Fit & FeaturesPlaid woven fabric with knit lining, minimal stretch, Collared neckline, Button-down front, Single chest pocket, Long sleeves with single-button detail, Long-length hem, relaxed fit, 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 Cozy Layer Plaid Woven Shacket in Ivory | Size: M | Knit Fabric/Woven Fabric
Perfectly Plaid Woven Oversized Cropped Shacket in Taupe
$14.97 $49.90
70% off
Perfectly plaid woven oversized cropped shacket is your go-to for laid-back vibes. With a collared neckline, button-down front, and flap pockets, it's perfect for any chill hangout or meet-up. Fit & FeaturesPlaid woven fabric with smooth woven lining, no stretch, Collared neckline, Long sleeves with single-button detail, Complete button-down front, Flap chest pockets, Cropped hem, Oversized fit, 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 Perfectly Plaid Woven Oversized Cropped Shacket in Taupe | Size: L | Woven Fabric
Oversized Outerwear
When it comes to oversized outerwear, you’re not just picking out a layer—you’re making an entrance. There’s something magnetic about a jacket that’s a little extra: the way it drapes, the way it moves, the way it instantly upgrades your whole vibe. Oversized outerwear is for the girl who knows her power and isn’t afraid to take up space—literally and figuratively. Whether you’re running out for coffee, dashing to class, or strutting into brunch with your crew, these statement pieces have your back (and your shoulders, and your arms, and maybe even your bestie’s if she needs to borrow it). The beauty of oversized fits is that they’re as versatile as your social calendar. Toss one over a slinky dress for that “I just threw this on” energy, or layer it with your favorite hoodie and leggings when you want to blur the line between cozy and cool. Think of it as your personal shield against the world—one that says, “Yeah, I’m here, and I’m owning it.”
Oversized outerwear isn’t just about comfort (though, let’s be real, it’s basically a wearable hug). It’s about attitude. It’s the go-to for those days when you want to look effortless but still serve a whole mood. Picture yourself walking into a late-night diner, your oversized coat trailing behind you, catching the neon light—suddenly, you’re the main character. Or maybe you’re gifting one to your ride-or-die who’s always cold, or your sister who’s obsessed with street style, or your mom who secretly loves to steal your clothes. These pieces are made for sharing, swapping, and showing off. They’re the ultimate “borrow and never return” item—so if you’re giving one as a gift, just know you might never see it again. And honestly? That’s the mark of a truly iconic wardrobe staple.
When picking out your oversized outerwear, pay attention to the little details that make a big difference—think pockets deep enough for snacks and secrets, luxe linings, or bold hardware that catches the light just right. Don’t be afraid to play with proportions; an oversized silhouette pairs just as well with skinny jeans as it does with wide-leg pants or a mini skirt and boots. And if you’re feeling overwhelmed by all the options, remember: your outerwear should feel like an extension of your personality. Go for the drama, the comfort, the confidence boost—whatever makes you feel unstoppable. If you’re ready to dive deeper into all things outerwear and explore more ways to turn sidewalks into runways, check out our full collection of Fashion Outerwear for even more inspo. Trust us, your closet (and your group chat) will thank you.