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.
$29.90
A brown ribbed knit fitted hoodie with a drawstring neckline and flattering seam detailing.
$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.
$36.90
A chic black ribbed knit skater dress with an off-the-shoulder neckline and long fitted sleeves.
$29.90
A pink 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.
$29.90
A pair of ivory woven palazzo pants featuring a high-rise waist, pleating, and flowy wide-leg silhouette.
$19.90
A breezy orange woven crop top featuring flowy short sleeves and a stylish tie-front design.
$9.97 $38.90 74% off
A brown knit bodycon midi dress with flare cuff sleeves and a stylish V-neckline.
$36.90
A heather grey knit mini dress with an off-the-shoulder neckline and A-line silhouette.
$32.90
A taupe ribbed knit pullover hoodie featuring a drawstring hood and tapered hems.
$29.90
A taupe ribbed knit bodycon mini dress with spaghetti straps and a scoop neckline for casual outings.
$32.90
A pair of black ponte knit flare pants with a high-rise waist and form-hugging fit.
$32.90
A soft brown cotton knit bolero sweater with relaxed long sleeves and an ultra-cropped open front.
$14.97 $34.90 57% off
An oversized navy blue sweatshirt with a cozy fleece lining and stylish graphic design.
$9.97 $29.90 67% off
A brown high-rise knit flare pant with a fold-over waist and ribbed hacci fabric for comfort.
$54.90
A chic oversized brown faux leather blazer with a lapel collar and single button closure.
$29.90
A seamless black romper with a form-hugging fit, ribbed knit fabric, and long sleeves.
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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 Natural | Size: XXS | 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 Taupe | Size: XS | 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 Black | Size: S | 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
The perfect sweater vest for a preppy babe vibe! It features a sleek V-neckline and a modern cropped hem perfect for pairing with high-waisted bottoms. Fit & FeaturesRibbed sweater knit fabric, moderate stretch, Sleeveless V-neckline, Fitted cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Preppy Babe V-Neck Cropped Sweater Vest in Black | Size: XS | Knit Fabric
From days by the beach to summer nights, this crochet sweater topper will keep you cute all season! Fit & FeaturesSheer crochet fabric, Fitted long sleeves with flare cuffs, Crew neck, Ultra-cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Too Cute Crochet Sweater Topper in Brown | Size: XS
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: M | 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: XS | Knit Fabric
Sun, sand, and this dress—name a better trio. The strapless twist neckline and open-knit crochet bring breezy beach goddess vibes with zero effort required. Perfect for sunset cocktails on vacay or a beach date! Fit & FeaturesCrochet fabric, knit lining, Strapless twist neckline, Curve-hugging fit, Center back slit, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Barefoot Bliss Strapless Crochet Maxi in Natural | Size: S | 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
Comfy Fall Outfits
Let’s be real: there’s nothing better than slipping into something that feels like a warm hug after a long day, or getting ready to head out with your crew knowing you look effortlessly put together and still insanely comfortable. Comfy outfits are the ultimate power move for anyone who wants to keep it cute without sacrificing coziness, whether you’re running errands, binge-watching your favorite series, or grabbing coffee with your ride-or-die. These are the looks you reach for when you want to keep your vibe chill but your style on point—the soft, lived-in fabrics, the relaxed fits that still show off your shape, and the little details that make you feel like the main character even on your laziest days. Think of these pieces as your personal hype squad, ready to back you up for spontaneous plans or those legendary nights in with your besties. They’re also total game-changers for gifting—because who wouldn’t want to unwrap something that says, “I care about your comfort and your drip”? Whether you’re shopping for your BFF, your sister, or treating yourself (because you deserve it, obviously), these picks are basically guaranteed to earn you MVP status.
When you’re building your comfy outfit lineup, it’s all about mixing and matching textures and silhouettes that work just as hard as you do. Look for buttery-soft knits, plush fleece, and stretch fabrics that move with you—because let’s be honest, nobody has time for stiff, scratchy clothes. Oversized layers are a must for that effortlessly cool, borrowed-from-my-crush energy, and don’t even get us started on the magic of a matching set. The best part? These pieces aren’t just for lounging at home; they’re made for living your best life wherever the day (or night) takes you. Picture yourself curled up with a pumpkin spice latte, scrolling your feed, or heading out for a spontaneous dinner date—comfy outfits aren’t just a vibe, they’re a lifestyle. And if you’re planning to level up your look for something a little more elevated, check out our curated picks for Fall Dinner Outfits—because you deserve to serve, no matter the occasion.
Shopping for comfy fits is your chance to show off your personality and create a wardrobe that feels like you—bold, fearless, and always ready for a good time. Don’t be afraid to play with colors, layer up with cozy accessories, or throw on a statement piece that makes you feel unstoppable. These are the clothes you’ll reach for again and again, the ones that make you feel at home in your own skin and ready to take on whatever comes your way. Whether you’re gifting a little piece of comfort to someone you love or just treating yourself to a major mood boost, remember: confidence is the best accessory, and a killer comfy outfit is the ultimate flex.