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.

Show Filters

Sort: Recommended

Size

Color

Price

All Filters

27 results

Sort

Windsor Comfy Trend Plaid Woven Oversized Shacket in Ivory

$59.90

An ivory plaid oversized shacket with woven fabric, perfect for stylish remote work and casual outings.

Sale

Cozy Layer Plaid Woven Shacket in Ivory

$26.97 $59.90 55% off

A stylish ivory plaid shacket with knit lining and button-down front, perfect for casual occasions.

Best Seller

Major Cutie Cargo Joggers Pant in Olive

$46.90

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

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 Chic Staple Ribbed Knit Skater Dress in Black

$36.90

A chic black ribbed knit skater dress with an off-the-shoulder neckline and long fitted sleeves.

Stay Cozy Ribbed Knit Pullover Hoodie in Taupe

$32.90

A taupe ribbed knit pullover hoodie featuring a drawstring hood and tapered hems.

Windsor 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.

Now Trending

Windsor Chic Icon Faux Fur Trim Suede Coat in Brown

$89.90

(2)

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: S | Faux Suede

Comfy Trend Plaid Woven Oversized Shacket in Ivory

$59.90

(2)

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: XS | Knit Fabric/Woven Fabric

Windsor Casually Cozy Plaid Woven Cropped Shacket in Navy Blue

$49.90

(1)

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: M | Woven Fabric

Sale

Windsor Cozy Layer Plaid Woven Shacket in Ivory

$26.97 $59.90
55% off

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: S | Knit Fabric/Woven Fabric

Windsor Caught On Camera Lace Up Mesh Topper in Black

$24.90

Instant edge, zero effort—this mesh topper changes the whole look. The sheer finish and lace up front add just enough drama to layer over bralettes, tanks, or statement tops for nights out. Fit & FeaturesSheer mesh fabric with stretch, Crew neckline with lace-up placket, Fitted long sleeves, Ultra-crop length, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Caught On Camera Lace Up Mesh Topper in Black | Size: S | Mesh Fabric/Sheer Mesh Fabric

Sheer Confidence Lace Mock Neck Long Sleeve Topper in Black

$26.90

Soft lace, sharp attitude. This lace mock neck long sleeve topper layers like a dream over your favorite corset or bralette, giving you that sculpted, ultra-cropped fit that feels both romantic and bold. Fit & FeaturesSheer lace fabric, high stretch, Mock neckline, front hook-eye closures, Long fitted sleeves, Ultra-cropped hem, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sheer Confidence Lace Mock Neck Long Sleeve Topper in Black | Size: XL | Lace Fabric/Sheer Lace Fabric

Windsor Island Luxe Metallic Knit Poncho in Gold

$24.90

Glow like the golden hour in this sheer metallic poncho that was made for sipping cocktails with a view. Lightweight and breezy, it’s the perfect topper for your bikini or a slinky resort night look. Fit & FeaturesSheer metallic knit fabric, Cropped poncho silhouette, Boat neckline , Draped fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Island Luxe Metallic Knit Poncho in Gold | Size: M/L | Knit Fabric

Comfy Fall Outfits

When it comes to cozying up for fall, there’s a certain magic in finding those pieces that feel like a warm hug without sacrificing style. Picture this: crisp air, golden leaves crunching under your boots, and you—wrapped in layers that are as soft as your favorite throw but still ready for a spontaneous coffee run or an impromptu photo session with friends. Comfy fall outfits aren’t just about staying warm; they’re about embracing the season’s slower pace, layering up in textures that invite touch, and building a wardrobe that works as hard as you do. Whether you’re heading out for pumpkin picking, catching up on campus, or just lounging at home with a new book and a mug of chai, these looks are designed to keep you feeling put-together and perfectly at ease. Think plush knits, relaxed joggers, and oversized shackets that blur the line between off-duty and on-point—because fall fashion is all about balance. It’s the season to lean into rich colors, tactile fabrics, and silhouettes that let you move (and snack) freely. If you’re shopping for yourself, consider how these pieces can flex with your schedule—easy to dress up with a boot or down with a slipper, always ready for a last-minute plan. And if you’re hunting for a gift, there’s nothing more thoughtful than a layer that feels personal and practical, especially for the friend who’s always cold or the sibling who’s just moved into their first apartment.

The beauty of comfy fall outfits is how universally loved they are—everyone has their own version of “cozy,” and these styles deliver on every front. For the student juggling early classes and late-night study sessions, soft sets and roomy sweaters are an instant mood boost (and a camera-ready option for those surprise Zoom calls). For the friend who treats every weekend like a mini getaway, think easy layers that pack well and transition from cabin mornings to city strolls without missing a beat. Even if your fall plans are less apple orchard and more Netflix marathon, having a rotation of go-to pieces means you’re always ready for whatever comes up—be it a spontaneous road trip, a bonfire invite, or just a needed self-care day. These looks also make ideal gifts for birthdays, housewarmings, or “just because” surprises, especially since they’re one-size-fits-most in spirit, if not in tag. There’s something undeniably special about gifting comfort—about knowing the recipient will think of you every time they slip into that extra-soft pullover or those fleece-lined joggers. And if you’re curating your own closet, now’s the time to swap out the summer linens for plush textures and deeper hues that feel right for the season. Don’t be afraid to mix and match—fall is all about layering, after all. If you’re looking for even more inspiration to refresh your lineup, explore our curated take on Fall Fashion Outfits for looks that go beyond the basics and help you show up exactly how you want, every single time.

Reset Your Password

Email Sent

Order Status

Comfy Fall Outfits

Home Comfy Fall Outfits

Now Trending

Comfy Fall Outfits

Related Collections