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.
$59.90
An ivory plaid oversized shacket with a collared neckline, perfect for casual virtual gatherings.
$46.90 - $49.90
A chic olive cargo jogger with high-rise waist, metal ring trims, and elastic cuffed hems.
$36.90
A chic black ribbed knit skater dress with an off-the-shoulder neckline and long fitted sleeves.
$29.90
A natural oversized knit sweater bolero with slouchy sleeves and an ultra-cropped hem.
$34.90
A cozy burgundy knit cardigan with a button-down front and cropped hem for versatile styling.
$36.90
A heather grey knit mini dress with an off-the-shoulder neckline and A-line silhouette.
$6.97 $29.90 77% off
A taupe ribbed knit bodycon mini dress with spaghetti straps and a scoop neckline for casual outings.
$54.90
A chic oversized brown faux leather blazer with a lapel collar and single button closure.
$32.90
A pair of black ponte knit flare pants with a high-rise waist and form-hugging 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 Pink | Size: M | 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 Burgundy | Size: S | 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 Burgundy | Size: L | Knit Fabric
Perfect for layering on chill evenings, this knit bolero sweater highlights your silhouette while providing just the right amount of coverage and warmth! Fit & FeaturesSoft cotton knit fabric, Relaxed long sleeves, Open front design, Ultra-cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cutie Pie Knit Bolero Sweater in Brown | Size: XS | Cotton/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: L | 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
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: S | Knit Fabric
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: XS | Knit Fabric
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: L
Crisp breeze? She’s ready. This striped sweater brings cozy charm with a throw-on-and-go fit made for coffee runs, apple picking, or romanticizing your Tuesday errands. Fit & FeaturesStriped pattern, soft knit stretch fabric, Crew neck, Long sleeves, Ultra-cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Crisp Breeze Striped Sweater Topper in Natural | Size: XS | Knit Fabric