Cute Winter Outfits
Cute winter outfits are basically your secret weapon for slaying chilly days and frosty nights—because who says you can’t look fire when it’s freezing? From cozy layers to playful textures, these looks serve up all the style inspo you need to keep your vibe hot even when the temps drop. Whether you’re headed out for a coffee run or planning a spontaneous snow day adventure, get ready to bundle up and turn every sidewalk into your runway.
$35 $49.90 30% off
A navy blue plaid shacket with faux wool fabric and a relaxed fit for casual styling.
$54.90
A chic taupe faux suede trench coat with a belted waist and double-breasted button closures.
$59.90
A brown plaid oversized shacket in faux wool with faux suede lining and chest pockets.
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Seasonal Favorite Faux Suede Shacket in Camel
$21.97 $49.90
56% off
The perfect faux suede shacket for layering during the chilly seasons! It features cozy long sleeves a button-up front, and convenient front pockets to help keep your hands warm. Style with booties. Fit & FeaturesSoft faux suede lined fabric, Long sleeves, Collar neckline, Button-up front closures, Front pockets, Relaxed silhouette, 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 Seasonal Favorite Faux Suede Shacket in Camel | Size: S
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
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: L | 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: M/L | Faux Suede
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 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: S | 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: M | 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: L | 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: M
Cute Winter Outfits
When it comes to curating cute winter outfits, you know the assignment: stay cozy, look iconic, and never let a little chill dull your shine. Whether you’re the queen of layered looks or just dipping your toes into the world of chunky knits and fuzzy textures, there’s something about winter fashion that just hits different. It’s that moment you throw on a plush faux fur jacket and suddenly feel like you’re starring in your own holiday rom-com, or when you wrap up in a scarf so soft it might as well come with its own comfort playlist. These pieces aren’t just about keeping warm—they’re about serving major looks while you’re at it. Think about those spontaneous snow day adventures with your ride-or-die crew, coffee runs that turn into impromptu photo shoots, or family gatherings where you want to wow the cousins you only see once a year. The best part? These styles aren’t just for you. They make the ultimate gift for your bestie who’s always freezing, your sister who’s obsessed with all things fluffy, or that cousin who never met a statement accessory she didn’t love. Gifting a cute winter piece is basically handing someone a whole season of good vibes and main character moments—wrap it up with a bow and you’re officially the MVP of gift-giving.
But let’s be real, winter dressing is an art—and you’re Picasso, babe. The trick is mixing textures, colors, and silhouettes until you’ve got a look that’s as unique as your group chat. Go bold with faux leather and plaid, or keep it sweet with cable knits and pastel hues. Layering is your secret weapon: think turtlenecks under slip dresses, oversized cardis over mini skirts, and boots that stomp through slush without ever sacrificing style. If you’re shopping for yourself, keep an eye out for those versatile pieces that transition from hot cocoa runs to late-night movie marathons without missing a beat. And if you’re shopping for someone else, consider their vibe—are they all about that effortless, off-duty model energy, or do they live for a little sparkle and drama? No matter who’s on your list (including you, bestie), cute winter outfits are all about making every day a little more magical, a little more memorable, and a lot more Insta-worthy. And when you’re ready to switch up the vibe or need inspo for those in-between moments, check out our Cute Casual Outfits for all the laid-back looks that still bring the heat. So go ahead—layer up, step out, and turn every sidewalk into your personal runway.