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.
$29.90
A pink oversized knit sweater bolero with slouchy sleeves and an ultra-cropped hem for cozy style.
$39.90
An ivory knit bolero with faux fur cuffs and collar, featuring an ultra-cropped hem and open front.
$29.90
A form-hugging black ribbed knit bodysuit with a turtleneck and long fitted sleeves.
$34.90
A cozy taupe knit cardigan with a button-down front and cropped hem for versatile styling.
$42.90
A brown cropped denim shacket with long sleeves, button cuffs, and convenient flap pockets.
$79.90
A brown faux leather trench coat featuring a belted waist, double-breasted closure, and long sleeves.
$59.90
A brown plaid oversized shacket in faux wool with faux suede lining and chest pockets.
$32.90
An ivory eyelash knit cardigan with a V-neckline and button-down front for a cozy fit.
$29.90
A brown ribbed knit fitted hoodie with a drawstring neckline and flattering seam detailing.
$32.90
A soft brown cotton knit bolero sweater featuring relaxed long sleeves and an ultra-cropped open front.
$54.90
A chic oversized brown faux leather blazer with a lapel collar and single button closure.
$52.90
An olive twill cropped jacket with a fleece-lined hoodie, perfect for stylish, cozy layering.
$36.90
A natural rib knit mini dress with a folded off-the-shoulder neckline and flattering skater silhouette.
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Layer on this sweater bolero for a sweet look and cozy feel! The sweater features slouchy long sleeves with ribbed cuffs, an open front design, an oversized silhouette, and an ultra-cropped hem on soft and stretchy knit fabric. Complete the look with strappy heels for a day out with bae! Fit & FeaturesSlouchy long sleeves, ribbed cuffs, Open front design, Ultra-cropped hem, Oversized silhouette, Sweater knit fabric, soft and stretchy, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet And Cozy Oversized Knit Sweater Bolero in Heathergrey | Size: XS | Knit Fabric
Cozy and charming, this knit cardigan offers a classic design with a button-down front for versatile styling options and a cropped hem. Fit & FeaturesKnit fabrication, moderate stretch , Button-down front , Long sleeves, Cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cozy Charm Cropped Knit Cardigan Sweater in Taupe | Size: XS | Knit Fabric
Bring your look together with a cropped knit cardigan that features a crew neckline, a button-down front, and fitted long sleeves. Pair with a pleated skirt and sneakers for a casual vibe! Fit & FeaturesKnit fabric with ribbed hems, plenty of stretch, Crew neckline, Button-down front , Long sleeves, Cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Staple Crew Neck Cropped Knit Cardigan Sweater in Black | Size: S | Knit Fabric
A sleeveless crop top featuring a preppy striped V-neckline, adjustable spaghetti straps for a customizable fit, and a striped crop hem. The stretchy knit fabric offers a polished look with plenty of stretch. Shop Matching Top And Bottom: Preppy Please Striped V-Neck Crop Top, Preppy Please Striped Pleated Knit SkortFit & FeaturesStretchy knit fabric, Long sleeves with striped cuffs, Striped front trim, Button front closures, Striped crop hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Preppy Please Striped Button Crop Sweater in Black | Size: M | Knit Fabric
The perfect sweater vest for a preppy babe vibe! It features a sleek V-neckline and a modern cropped hem perfect for pairing with high-waisted bottoms. Fit & FeaturesRibbed sweater knit fabric, moderate stretch, Sleeveless V-neckline, Fitted cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Preppy Babe V-Neck Cropped Sweater Vest in Black | Size: XS | Knit Fabric
From days by the beach to summer nights, this crochet sweater topper will keep you cute all season! Fit & FeaturesSheer crochet fabric, Fitted long sleeves with flare cuffs, Crew neck, Ultra-cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Too Cute Crochet Sweater Topper in Brown | Size: XS
Get cozy in this eyelash knit button-down cardigan sweater. With a V-neck, long sleeves, and fitted cropped hem, it's your go-to for effortless style and comfort. Fit & FeaturesEyelash ribbed knit fabric, moderate stretch, V-neckline, Long sleeves, Button-down front, Fitted cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Adorably Cozy Eyelash Knit Button-Down Cardigan Sweater in Ivory | Size: M | Knit Fabric
Embrace effortless style with this crochet sweater perfect for styling over a swimsuit or tank top. This sweater offers a blend of comfort and allure with relaxed long sleeves, a flirty one-shoulder neckline, and a cropped hem. Fit & FeaturesSheer crochet knit fabric, One-shoulder neckline, Relaxed long sleeves, Cropped length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Breezy Nights Crop Crochet Sweater in Black | Size: XS | Knit Fabric
Sun, sand, and this dress—name a better trio. The strapless twist neckline and open-knit crochet bring breezy beach goddess vibes with zero effort required. Perfect for sunset cocktails on vacay or a beach date! Fit & FeaturesCrochet fabric, knit lining, Strapless twist neckline, Curve-hugging fit, Center back slit, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Barefoot Bliss Strapless Crochet Maxi in Natural | Size: S | Knit Fabric
Windsor Charming Duo Long Sleeve Bolero in Light Blue
$12.97 $29.90
57% off
A charming long sleeve bolero you'll adore for brunch or family gatherings! Pair with the matching dress for a complete look. Fit & FeaturesSoft rib knit stretchy fabric, Fitted long sleeves, Open front design, Ultra-cropped hem, Runs true to size, Shop The Matching Dress: Charming Duo Strapless Skater Mini Dress Free Shipping on All Orders Over $75. | Windsor Charming Duo Long Sleeve Bolero in Light Blue | Size: L | Knit Fabric/Stretchy Fabric
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.