Oversized Clothing

Oversized clothing is the ultimate vibe for those who love to mix comfort with a splash of street-chic flair. Whether you're strutting down city sidewalks or chilling at your fave coffee spot, these roomy fits are all about embracing your inner cool girl. Think effortlessly stylish layers that let you move, groove, and make waves wherever you go. From slouchy sweaters that feel like a warm hug to baggy jeans that scream laid-back confidence, oversized clothing is your ticket to looking fab without even trying. So go ahead, take on the world in style that's as bold and fearless as you are!

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Windsor Sweet And Cozy Oversized Knit Sweater Bolero in Natural

Best Seller

Windsor Sweet And Cozy Oversized Knit Sweater Bolero in Natural

$29.90

A natural oversized knit sweater bolero with slouchy sleeves and an ultra-cropped hem.

Windsor Comfy Trend Plaid Woven Oversized Shacket in Ivory

$59.90

An ivory plaid oversized shacket with a collared neckline, perfect for casual virtual gatherings.

Keep It Trendy Oversized Faux Leather Blazer in Brown

$54.90

A chic oversized brown faux leather blazer with a lapel collar and single button closure.

Major Cutie Cargo Joggers Pant in Olive-2

Best Seller

Major Cutie Cargo Joggers Pant in Olive-2

$46.90

A chic olive cargo jogger with high-rise waist, metal ring trims, and elastic cuffed hems.

Cuddle Weather Eyelash Knit Cardigan Sweater in Ivory

$42.90

A soft ivory cardigan with cozy eyelash knit fabric and relaxed dolman sleeves for effortless style.

Casually Cozy Plaid Woven Cropped Shacket in Navy Blue

$49.90

A navy blue plaid shacket with a relaxed fit, collared neckline, and cropped cinched hem.

Casual Cool Vibes Hoodie Bomber Jacket in Taupe

$42.90

A taupe nylon hoodie bomber jacket with a relaxed fit and drawstring hood for casual wear.

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Windsor Sweet And Cozy Oversized Knit Sweater Bolero in Ivory

$29.90

(49)

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 Ivory | Size: L | Knit Fabric

Windsor Cozy Charm Cropped Knit Cardigan Sweater in Burgundy

$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 Burgundy | Size: S | 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

Sale

Cozy Mood Cable Knit Pullover Sweater in Rust

$17.97 $34.90
49% off

(6)

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

Windsor Layer Check Mock Neck Zip-Up Sweater in Black

$36.90

(5)

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

Spice And Everything Nice Tie Back Sweater in Rust

$36.90

(3)

Serving sweater weather with a side of flirt. The mock neck keeps you cozy, while the open tie back makes sure your fall fit still has a little spice! Fit & FeaturesSoft knit stretch fabric, Mock neck, Relaxed long sleeves, Open tie-back detail, Cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Spice And Everything Nice Tie Back Sweater in Rust | Size: M | Knit Fabric

Windsor 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: S

Windsor Sweet Drama Removable Faux Fur Lace Cardigan Sweater in Pink

$39.90

(3)

Soft, sweet, and a little extra—in the best way. This sheer lace cardigan layers on romance with faux fur trim for the perfect amount of drama. Fit & FeaturesSheer lace fabric, Faux fur trim at collar and cuffs, loop and button attachments, Hook-eye front closures, Long sleeves, Cropped length, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Drama Removable Faux Fur Lace Cardigan Sweater in Pink | Size: S | Lace Fabric/Sheer Lace Fabric

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

Oversized Clothing

Oversized clothing is more than just a passing trend—it’s a whole vibe, a sartorial exhale that says comfort and confidence don’t have to be mutually exclusive. When the weather cools down and layering becomes less of a style choice and more of a survival tactic, oversized fits step up to the plate. Think roomy pullovers that double as blankets on chilly mornings, slouchy tees you can knot or tuck depending on your mood, and billowy button-downs that somehow always look like you borrowed them from someone with impeccable taste. There’s a certain freedom in the extra fabric, a sense that you can move through your day—whether that’s running errands, heading to class, or just hanging out at home—without feeling restricted or overdone. The best part? Oversized pieces are the ultimate blank canvas. Dress them up with a mini skirt and tall boots, or keep it low-key with leggings and sneakers. You can layer them over turtlenecks, under jackets, or let them shine solo. They’re the wardrobe MVPs you’ll reach for again and again, especially as the days get shorter and the urge to stay cozy gets stronger.

Gift-wise, oversized clothing is a no-brainer. There’s something universally appealing about an item that fits a little looser, a little softer, and feels like an instant hug. For friends who are always cold, siblings who love a borrowed-from-the-boys aesthetic, or that one person who’s impossible to shop for, oversized styles are a safe bet. They’re forgiving when it comes to sizing, which makes them perfect for holiday gifting or low-pressure Secret Santa swaps. Picture this: it’s a Sunday morning, coffee in hand, and you’re wrapped up in an oversized pullover that’s just roomy enough to make you feel cocooned, but still cute enough for a spontaneous brunch invite. These pieces aren’t just for lounging, either. They’re for those “throw on and go” moments—school drop-offs, quick coffee runs, or last-minute plans that pop up when you least expect them. And if you’re the type who loves to share your closet, oversized styles are the easiest to lend (and the hardest to get back). If you’re building out your layering game for the season or just want a single piece that does the most, don’t sleep on the versatility of Oversized Pullovers—they’re the definition of effortless, every day, and absolutely essential.

When you’re shopping for oversized looks, pay attention to the fabric and the cut. The right material can make all the difference—think soft knits that drape just right, crisp cottons that hold their shape, or cozy fleeces that feel like a warm embrace. Look for thoughtful details like dropped shoulders, exaggerated sleeves, or side slits that add movement and dimension. Don’t be afraid to experiment with proportions, either. An oversized top with fitted bottoms creates instant balance, while head-to-toe volume can be a bold, editorial moment if you’re feeling adventurous. The beauty of oversized clothing is that it works for everyone and every mood—whether you’re channeling laid-back cool, going for a romantic, borrowed-from-the-boys vibe, or just want something that feels like a sartorial security blanket. Embrace the ease, play with the possibilities, and let your style breathe a little. This season, oversized isn’t just a look—it’s a lifestyle.

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