Stylish Sweatshirts

Stylish sweatshirts are the ultimate wardrobe MVPs that blend comfort with flair, making them your go-to for effortless cool. Whether you're hitting the books or brunching with your squad, these chic staples keep you looking fab and feeling cozy. Embrace the laid-back luxe of stylish sweatshirts that take you from Netflix marathons to spontaneous adventures in a heartbeat. It's time to level up your casual game and let your style shine through in every hue and print!

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Layer Check Mock Neck Zip-Up Sweater in Black

$36.90

A black plaid knit sweater featuring a ribbed mock neck, fitted silhouette, and front zip-up closure.

Windsor Casual Slay Star 24 Knit Sweater in Ivory

$36.90

A sporty ivory knit sweater featuring star print sleeves, striped trim, and bold graphic details.

Crisp Breeze Striped Sweater Topper in Natural

$32.90

A cozy striped sweater in natural knit fabric with a crew neck and ultra-cropped hem.

Spice And Everything Nice Tie Back Sweater in Rust

$36.90

A soft rust knit sweater featuring a cozy mock neck and a flirty open tie-back detail.

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Sweet And Cozy Oversized Knit Sweater Bolero in Navy Blue

$29.90

(47)

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 Navy Blue | Size: XS | Knit Fabric

Cozy Charm Cropped Knit Cardigan Sweater in Black

$34.90

(14)

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 Black | Size: M | Knit Fabric

Windsor Sunday Edit Off-The-Shoulder Sweater in Blue

$32.90

(7)

The sweater that says “effortless but cute” every time. With a slouchy off-the-shoulder neckline and relaxed fit, it’s perfect for a cozy-meets-chic vibe. Fit & FeaturesSoft knit stretchy fabric , Off-the-shoulder neckline, Long sleeves, Crop-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sunday Edit Off-The-Shoulder Sweater in Blue | Size: L | Knit Fabric/Stretchy Fabric

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Cozy Mood Cable Knit Pullover Sweater in Rust

$17.97 $34.90
49% off

(4)

Fit & FeaturesOpen cable knit fabric, Ribbed hems, Crew neckline, Long sleeves, Mid-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cozy Mood Cable Knit Pullover Sweater in Rust | Size: L | Knit Fabric

Breezy Nights Crop Crochet Sweater in Black

$29.90

(4)

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: L | Knit Fabric

Windsor Layer Check Mock Neck Zip-Up Sweater in Black

$36.90

(4)

Cozy, but make it cool. This mock neck zip-up sweater gives effortless flair, perfect for layering or styling on off-duty days. Fit & FeaturesSoft, stretchy knit fabric, Fitted long sleeves, rib knit cuffs, Rib knit mock neckline, Front zip-up closure, Fitted silhouette, Rib knit hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Layer Check Mock Neck Zip-Up Sweater in Black | Size: M | Knit Fabric

Windsor Cuddle Weather Eyelash Knit Cardigan Sweater in Ivory

$42.90

(3)

Snuggle up in this eyelash knit cardigan sweater. With its soft, cozy fabric and relaxed dolman sleeves, it's your go-to for effortless chic vibes. Fit & FeaturesSoft, cozy eyelash knit fabric, Dolman relaxed long sleeves, Open front design, Relaxed fit hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cuddle Weather Eyelash Knit Cardigan Sweater in Ivory | Size: S | Knit Fabric

Cool Intentions Long Sleeve Knit Bolero in Brown

$29.90

(3)

Layer it, slay it—this bolero is the ultimate fall cool-girl combo. Throw it on with your fave crop top or dress and you’re instantly serving street style. Fit & FeaturesKnit fabric, Long sleeves, Open front design, Ultra-cropped length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cool Intentions Long Sleeve Knit Bolero in Brown | Size: XS

Windsor Fall Mornings Chenille Knit Cardigan Sweater in Ivory

$34.90

(2)

The cardigan your fall lineup was waiting for. This ribbed chenille cardigan wraps you in an ultra-soft, cozy feel with a relaxed drape that goes perfectly over your favorite knits, dresses, or lounge sets. Ideal for crisp mornings, coffee runs, and everything cozy in between. Fit & FeaturesSoft chenille knit fabric, Open front draped design, Long sleeves, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fall Mornings Chenille Knit Cardigan Sweater in Ivory | Size: M | Knit Fabric

Adorably Cozy Eyelash Knit Button-Down Cardigan Sweater in Ivory

$32.90

(2)

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: L | Knit Fabric

Stylish Sweatshirts

There’s something about slipping into a stylish sweatshirt that just hits different—especially when the weather outside is doing its best impression of a snow globe. January is officially cozy season, and if your closet isn’t already stocked with a few go-to sweatshirts, now’s the time to change that. Think of these as the ultimate mood boosters: soft, effortless, and always ready to make you feel pulled together, even when the rest of your day is anything but. Whether you’re a die-hard fan of the classic windsor hoodie or you gravitate toward a cropped sweater that pairs perfectly with high-waisted jeans, sweatshirts have graduated far beyond gym class. They’re the unsung heroes of winter layering, the secret sauce to looking cute on coffee runs, and the unofficial uniform for everything from late-night study sessions to spontaneous road trips with your crew.

Styling a trendy sweatshirt isn’t just about comfort—it’s about bringing a little personality to your everyday look. Maybe you’re into oversized silhouettes that feel like a wearable hug, or maybe you love the way a fitted windsor sweatshirt looks tucked into a pleated mini skirt. Either way, these pieces play well with just about anything in your wardrobe. Toss one over a slip dress for an unexpectedly chic combo, or layer it under a puffer for that “I didn’t try, but I definitely did” vibe. And if you’re shopping for someone else (think: that friend who lives in loungewear, your sister who’s always cold, or your roommate who borrows your clothes without asking), a stylish sweatshirt is a foolproof gift that says “I get you” without having to say a word. With so many options—graphic prints, bold colors, luxe textures, and playful details—finding the right fit is more about expressing your mood than following any rules. The best part? These are the pieces that move with you, from lazy Sunday mornings to last-minute dinner invites, making them a smart investment for anyone who values both style and versatility.

If you’re looking to level up your winter wardrobe beyond sweatshirts, consider exploring the world of sweater dresses for a look that’s equal parts cozy and elevated. They’re perfect for those days when you want to look put-together with minimal effort—just add boots and go. For more inspiration, check out our collection of Trendy Sweater Dresses and discover how easy it is to stay warm without sacrificing style. No matter how you wear them, sweatshirts are proof that comfort and fashion aren’t mutually exclusive. They’re the pieces you reach for on repeat, the ones you pack for every trip, and the reason your friends keep asking, “Where’d you get that?” This season, let your sweatshirts do the talking—and trust us, they’ve got plenty to say.

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