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
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.
$18.97 $36.90 49% off
A chic oatmeal skater dress with a ribbed knit, off-the-shoulder neckline, and long fitted sleeves.
$29.90
A pink oversized knit sweater bolero with slouchy sleeves and an ultra-cropped hem for cozy style.
$46.90
A brown woven midi dress with a ditsy floral pattern, corset bodice, and high front slit.
$34.90
A comfy black ribbed knit pant with a mid-rise waist and stylish flare hem.
$9.97 $38.90 74% off
A brown knit bodycon midi dress featuring flare cuff sleeves with tie accents and a V-neckline.
$54.90
A tan floral tapestry cropped jacket with a collared neckline, button-down front, and dual pockets.
$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.
$36.90
A sheer crochet kimono in natural with slouchy sleeves and an open front design.
$36.90
A black rib knit romper with long sleeves and a flattering square neckline for casual outings.
$12.97 $29.90 57% off
A blue knit crop sweatshirt with an oversized fit and bold front "7" graphic.
$32.90
A pair of black ponte knit flare pants with a high-rise waist and form-hugging fit.
$29.90
A taupe ribbed knit bodycon mini dress with a scoop neckline and spaghetti straps.
$32.90
A white cotton-blend cropped hoodie with a relaxed fit and drawstring hood for everyday comfort.
$34.90
An oversized navy blue sweatshirt with a cozy fleece lining and stylish graphic design.
$54.90
A chic oversized brown faux leather blazer with a lapel collar and single button closure.
$59.90
An ivory plaid oversized shacket with a collared neckline and chest pocket, perfect for casual wear.
$9.97 $29.90 67% off
A brown high-rise knit flare pant with a fold-over waist and ribbed hacci fabric for comfort.
$16.97 $39.90 57% off
An oversized grey sweatshirt with a soft fleece lining and New York embroidered script.
$29.90
A comfy grey zip-up crop jacket with stretchy rib knit fabric and a mock neckline.
$13.97 $32.90 58% off
An ultra-cropped ivory sweater knit topper with ribbed fabric and long sleeves for a cozy look.
$29.90
A seamless black romper with a form-hugging fit, ribbed knit fabric, and long sleeves.
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This halter top is designed with a double-lined brushed knit fabric offering plenty of stretch for comfortable wear. It features a sleeveless plunging V-neckline with a trendy halter strap, an open back, a mid-length hem to pair with your fave low-rise jeans, and a form-hugging fit. Fit & FeaturesStretchy double-lined brushed knit fabric, Plunge V-neckline, Halter strap, Open back, Mid-length hem, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Trendy Find Knit Halter Top in Ivory | Size: S | Knit Fabric
Getting dressed is a stylish breeze when you have this basic crew neck tee with a flirty open back design to elevate your favorite bottoms! Fit & FeaturesSmooth stretchy knit fabric, Crew neck, Short sleeves, Open back design, Fitted crop hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Baby Got Back Basic Crew Neck Crop T-Shirt Top in Black | Size: XS | Knit Fabric
This sassy graphic tee features a crew neckline, short cap sleeves, a script reading "Extra Spicy Margarita Club," and a fitted cropped hem. Perf for happy hour, style with jeans and heels. Fit & FeaturesCotton fabric with moderate stretch, Crew neckline, Short cap sleeves, Script reading "Extra Spicy Margarita Club", Fitted cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Extra Spicy Margarita Club Graphic T-Shirt Top in White | Size: M | Cotton
This graphic tee is perfect for the girlies with attitude! It features a front graphic script that reads "Born To Yap" and a fitted crop length hem. Style with denim jeans and sneakers. Fit & FeaturesCotton-blend knit stretchy fabric , Graphic front script reads "Born To Yap", Crew neck, Cap sleeves, Fitted crop length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Born To Yap Graphic T-Shirt Top in Pink | Size: XS | Cotton/Knit Fabric/Stretchy Fabric
This graphic tee features a classic crew neckline, short sleeves, and a sassy front graphic script that reads "I'm Too Pretty For This" along the cropped fitted hem. Perfect for casual styling with jeans or a skirt. Fit & FeaturesStretchy knit fabric, Crew neckline, Short sleeves, Front graphic script reads "I'm Too Pretty For This", Cropped fitted hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor I'm Too Pretty For This Crop Graphic T-Shirt Top in White | Size: S | Knit Fabric
Every fashionista needs this long sleeve bodysuit to create dressed-up and down looks! Pair with a pleated skirt. Fit & FeaturesRibbed knit fabrication, double-lined, Square neckline, Fitted long sleeves, Snap button closure, Thong bottom coverage, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Appeal Ribbed Knit Long Sleeve Bodysuit Top in Black | Size: L | Knit Fabric
A smooth and essential long sleeve bodysuit you'll love to pair with jeans or skirts. The bodysuit is designed in a flattering form-hugging silhouette with a sleek thong bottom for a seamless look. Complete the look in trendy cargo pants. Fit & FeaturesSmooth, soft knit fabric, moderate stretch, Fitted long sleeves, Crew neck, Form-hugging silhouette, Thong bottom, snap-button closures, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Smooth Moves Long Sleeve Crew Neck Bodysuit Top in Pink | Size: M | Knit Fabric
Flaunt your sassy self in this trendy graphic tee featuring a front script that reads "No Hard Feelings" and a fitted crop hem. Pair with high-rise pants and sneakers. Fit & FeaturesCotton-blend knit fabric, moderate stretch, Short sleeves, Crew neck, Front script that reads "No Hard Feelings", Fitted crop hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor No Hard Feelings Graphic T-Shirt Top in Navy Blue | Size: M | Cotton/Knit Fabric
Play up your femme sass with this lace bra graphic crop tee, perfect for elevating a pair of jeans! Fit & FeaturesCotton knit stretchy fabric, Short sleeves, Crew neckline, Lace bra graphic, Cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Femme Sass Lace Bra Graphic T-Shirt Top in White | Size: M | Cotton/Knit Fabric/Stretchy Fabric
Channel a wild and free vibe in this trendy oversized tee featuring a bull rider and desert scenery graphic and a western-inspired script. Edge up the look with distressed denim and combat boots! Fit & FeaturesKnit fabric, moderate stretch, Crew neckline, Short sleeves, Bull rider and desert scenery graphic, Script reading "Cantina Est. 1978, El Toro, Open 24 Hrs!, West Village, San Antonio, Texas", Oversized fit, Free Shipping on All Orders Over $75. | Windsor Wild And Free Oversized Graphic T-Shirt Top in Black | Size: L
Comfy Fall Outfits
When it comes to leveling up your style game while keeping things ultra-cozy, there’s nothing quite like a wardrobe full of comfy outfits that are ready for anything on your calendar. Whether you’re headed to a coffee date with your besties, powering through a study session, or just vibing at home with your favorite playlist on repeat, comfort is the ultimate flex. The best part? You don’t have to sacrifice style for softness. Think plush knits, relaxed silhouettes, and buttery-soft fabrics that move with you—pieces that basically feel like a warm hug but look like you totally have your life together (even if you hit snooze three times). These are the outfits you’ll want to reach for on those days when you need to look cute in a flash, or when you just want to wrap yourself up and conquer your to-do list with zero distractions. The right comfy outfit can double as your secret weapon for everything from spontaneous road trips to last-minute movie marathons, making sure you’re always ready for whatever adventures pop up.
Comfy outfits aren’t just for lounging—they’re the go-to pick for anyone who loves to blur the lines between laid-back and put-together. Picture yourself running errands in a soft, slouchy set that still looks chic enough to turn heads, or gifting your ride-or-die friend something that says “I know you love to be cozy, but you also love to be cute.” These looks are perfect for gifting, especially for birthdays, care packages, or just because your BFF deserves a little extra comfort in her life. And if you’re shopping for yourself (because self-love is the best kind of love), keep an eye out for details like stretchy waistbands, oversized fits, and breathable fabrics that keep you feeling fresh from morning to night. Layering is your best friend here—throw on a lightweight cardigan or a cute shacket for those unpredictable weather days, and don’t forget to accessorize with fuzzy socks or a playful beanie for that extra pop of personality. If you’re all about that one-and-done vibe, check out our collection of Comfy Dresses for effortless style that transitions from chill hangs to spontaneous plans in a heartbeat.
No matter your plans, comfy outfits are the ultimate power move for anyone who wants to look good and feel even better. They’re the pieces you’ll reach for when you want to channel main character energy without breaking a sweat (or the bank), and they’ll have your back whether you’re crashing on your couch or heading out for late-night ice cream runs. It’s all about finding those staple pieces that work as hard as you do—mix and match them to fit your mood, your plans, and your wildest dreams. So go ahead, treat yourself (or your bestie) to something soft, stylish, and totally you. Because when you feel comfortable, you can take on anything—and look amazing doing it.