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.
$59.90
A stylish ivory plaid shacket with knit lining and button-down front, perfect for casual occasions.
$46.90 - $49.90
A chic olive cargo jogger with high-rise waist, metal ring trims, and elastic cuffed hems.
$29.90
A pink oversized knit sweater bolero with slouchy sleeves and an ultra-cropped hem.
$46.90
A brown woven midi dress with a ditsy floral pattern, corset bodice, and high front slit.
$36.90
A heather grey knit mini dress with an off-the-shoulder neckline and A-line silhouette.
$54.90
A chic oversized brown faux leather blazer with a lapel collar and single button closure.
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It's the season for this plaid oversized shacket to come out and play! Keep cozy and cute in this shacket perfect for styling with boots. Fit & FeaturesFaux wool fabrication, faux suede lining, no stretch, Plaid pattern, Collared neckline, Long sleeves with single button cuff, Button-down front, Chest pockets with buttoned flap closure, Oversized fit, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Plaid Passion Oversized Faux Wool Shacket in Brown | Size: S/M | Faux Suede
Casually cozy, this plaid woven shacket features a collared neckline, long sleeves, a button-down front with buttoned chest pockets, and a cropped cinched hem with an overall relaxed fit. Layer over a basic top with a denim skirt and booties! Fit & FeaturesPlaid woven fabric, no stretch, Collared neckline, Long sleeves with single-button detail, Button-down front, Dual buttoned chest pockets, Cropped hem, elastic cinched back hem, relaxed fit, Runs true to size, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Casually Cozy Plaid Woven Cropped Shacket in Navy Blue | Size: L | Woven Fabric
Throw it on and suddenly your everyday plans feel styled. This plaid woven oversized shacket layers easily over tanks and tees, giving cozy structure without trying too hard. Fit & FeaturesPlaid printed woven fabric with knit lining, Collared neckline, Long sleeves with single-button detail, Complete button-down front, Chest pocket, Oversized fit, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Comfy Trend Plaid Woven Oversized Shacket in Ivory | Size: M | Knit Fabric/Woven Fabric
Get comfy in the cozy layer plaid woven shacket! With a relaxed fit, button-down front, and chic plaid pattern, it's perfect for casual hangouts. Total vibe! Fit & FeaturesPlaid woven fabric with knit lining, minimal stretch, Collared neckline, Button-down front, Single chest pocket, Long sleeves with single-button detail, Long-length hem, relaxed fit, Runs true to size, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Cozy Layer Plaid Woven Shacket in Ivory | Size: M | Knit Fabric/Woven Fabric
The vintage-chic coat that instantly upgrades your whole mood. With plush faux fur trim and a smooth faux suede finish, it’s made for cozy glam and instant confidence. Fit & FeaturesFaux suede fabric, faux fur trims, Wide lapel collared neckline, Long sleeves, Tie-front belt, Double-breasted button-front design, dual front pockets, Long-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Icon Faux Fur Trim Suede Coat in Brown | Size: M | Faux Suede