Comfy Fall Outfits
Comfy fall outfits are basically the love language of every Windsor girl who wants to slay and stay cozy at the same time. Whether you’re running errands, hitting up brunch, or just vibing with your crew, these looks are all about maximum comfort with a side of “wow, where’d you get that?” Energy. Get ready to layer up, lounge out, and turn every sidewalk into your personal runway—because when it comes to comfy fall outfits, you never have to choose between chill and chic.
$36.90
A cozy ivory knit poncho featuring a flowy silhouette, soft boat neckline, and asymmetrical hem.
$46.90
A chic olive cargo jogger with high-rise waist, metal ring trims, and elastic cuffed hems.
$29.90
An oversized yellow knit bolero with slouchy long sleeves, ribbed cuffs, and an ultra-cropped hem.
$36.90
A chic black ribbed knit skater dress with an off-the-shoulder neckline and long fitted sleeves.
$42.90
A black hacci rib knit midi dress featuring long sleeves, a sweetheart neckline, and a chic side slit.
$29.90
A brown knit bolero featuring long sleeves, an open front, and an ultra-cropped hem for easy layering.
$14.97 $29.90 50% off
A chartreuse ribbed knit crop jacket featuring a zip-up front, mock neckline, and fitted long sleeves.
$42.90
A chic ivory ribbed knit midi dress featuring a mock neckline, keyhole bust, and bodycon silhouette.
$32.90
A cozy brown ribbed knit bolero with balloon sleeves and a modern cropped open-front design.
$36.90
A fuzzy brown rib knit crop sweater featuring a quarter zip and slouchy long sleeves.
$32.90
A plush beige faux fur shawl that adds a cozy, polished touch to any ensemble.
$32.90
A cozy taupe cable knit bolero featuring balloon sleeves and an open front for effortless layering.
$36.90
A brown denim skort featuring a lace-up front, mid-rise waist, and comfortable shorts backing.
$34.90
A black ribbed chenille knit cardigan with an open front and long sleeves for a cozy, relaxed fit.
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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 Black | Size: M | Knit Fabric
Cozy with a little flirt built in. This cropped cable knit cardigan hits that perfect balance between soft texture and shape, making it an easy throw-on sweater to elevate your favorite denim looks. Fit & FeaturesSoft cable knit fabric, V-neckline with dual button front closures, Voluminous long sleeves with rib knit cuffs, Crop-length curved hemline, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Off Duty Charm Cable Knit Crop Cardigan Sweater in Pink | Size: L | Knit Fabric
Sheer, shimmery, and not here to blend in. This sequin crochet fringe poncho is the ultimate layer when your bikini top or bralette deserves a little extra attention, but you still want that effortless, thrown on and thriving vibe. Fit & FeaturesLightweight sheer crochet fabric, Sequin embellishments, Relaxed poncho silhouette, Open neckline with easy slip-on design, Fringe hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Bare Minimum Drama Sequin Crochet Fringe Poncho in Brown | Size: M
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
This isn’t your average cardigan—it’s a full-on vibe. With its removable faux fur collar and tie-front detail, it’s a glam-meets-effortless look that's forever chic. Fit & FeaturesRibbed knit fabric, moderate stretch, Faux fur neckline is removable, V-neckline, Open tie-front design, Mid-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Chic Removable Faux Fur Tie-Front Cardigan Sweater in Black | Size: S | Knit Fabric
A cozy essential with a cool-girl twist. This fuzzy rib knit quarter zip sweater brings the perfect mix of soft and slouchy for those “cute but comfy” days with a coffee in hand! Fit & FeaturesFuzzy rib knit fabric, Quarter zip-up front closure collar neckline, Slouchy long sleeves, Crop-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cuddle Season Crop Sweater in Taupe | Size: S | Knit Fabric
Layered looks just got interesting. This ribbed knit long sleeve topper frames your outfit with an ultra-cropped cut that feels styled without trying too hard—perfect for nights out, casual plans, or that last-minute outfit switch. Fit & FeaturesUltra-cropped topper silhouette, Ribbed knit fabric with high stretch, Long fitted sleeves, Crew neckline, Front button details, Runs true to size, Bandeau pictured not included, Free Shipping on All Orders Over $75. | Windsor Level Up Ribbed Knit Long Sleeve Topper in Black | Size: XS | Knit Fabric
Your new favorite throw-on layer for cozy-chic moments. This ribbed bolero sweater brings that soft, lived-in feel with a modern cropped cut and easy balloon sleeves—perfect for topping off tanks, corsets, or lounge looks. Fit & FeaturesSoft stretchy rib knit fabric, Balloon long sleeves, Open front design, Crop-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Effortless Chill Ribbed Bolero in Brown | Size: S | Knit Fabric
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 Black | Size: XS | Knit Fabric
Sweet, but with claws. This tie-front crop cardigan brings cozy meets chaos with its soft knit fabric and removable leopard faux fur trim. Whether you style it layered or solo, it’s the ultimate “don’t mess, I’m vibing” kind of top. Fit & FeaturesSoft rib knit stretchy fabric, Removable leopard faux fur collar, Tie-front closure, Fitted long sleeves with leopard removable faux fur cuffs, Cropped-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Wild Chic Leopard Removable Faux Fur Cardigan Sweater in Black | Size: L | Knit Fabric/Stretchy Fabric