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.
Home Comfy Fall Outfits
- Recommended
- Most Popular
- Price - Low to High
- Price - High to Low
$59.90
An ivory plaid oversized shacket with woven fabric, perfect for stylish remote work and casual outings.
$46.90
A chic olive cargo jogger with high-rise waist, metal ring trims, and elastic cuffed hems.
$29.90
A natural oversized knit sweater bolero with slouchy sleeves and an ultra-cropped hem.
$32.90
A taupe ribbed knit pullover hoodie featuring a drawstring hood and tapered hems.
$54.90
A chic oversized brown faux leather blazer with a lapel collar and single button closure.

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Slip into the luxe vibes of Mayra! Designed to highlight your figure, this formal satin dress delivers a chic form-hugging fit and a high slit for effortless movement. Fit & FeaturesSmooth satin-knit fabric, moderate stretch, Sleeveless square neckline, spaghetti straps, Fitted bodice, side hip pleating, Form-fitting silhouette, high-cut front slit, Floor-length hem, Style runs small, Where to Wear:Homecoming, weddings, black-tie parties, galas, military balls, engagement parties, rehearsal dinners, bridal celebrations, birthday events, milestone celebrations Free Shipping on All Orders Over $75. | Windsor Mayra Formal Satin Slit Long Dress in Navy Blue-2 | Size: M | Satin Fabric
Create a captivating entrance in this formal wrap dress for your next soiree. All eyes are on you in this stylishly chic long formal dress with a plunging V-neckline to perfectly display a sparkling rhinestone lariat or delicate layers of dainty necklaces. Fit & FeaturesCrepe fabric, moderate stretch, Asymmetrical wrap V-neckline, Adjustable spaghetti straps, Ruched detailing, slim-fit bodice, High front slit, floor-length wrap silhouette, Runs true to size, Where to Wear:Prom, black-tie weddings, and formal parties. Free Shipping on All Orders Over $75. | Windsor Sasha Formal High Slit Wrap Dress in Black | Size: M | Rhinestone
Chic and glamorous, the Rowena sequin mermaid long dress will stylishly elevate your formal night-out look. With a lace-up strap design and fitted mermaid silhouette with a high slit, you'll deliver stunning style. Fit & FeaturesSheer mesh fabric, knit lining, moderate stretch, embroidered sequin scroll design, Sleeveless square neckline, padded bust, Spaghetti straps, open back, lace-up strap design, tie closure, Lower back zipper with hook and eye closure, High waist seam, Fitted floor-length mermaid silhouette, high front slit, Runs true to size, Where to Wear:Prom, black-tie parties and galas, fancy engagement parties Free Shipping on All Orders Over $75. | Windsor Rowena Sequin Mermaid Dress in Navy Blue | Size: M | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
Lavish yourself with a luxe formal dress that elevates your special occasion outfit! Cheyenne features a one-shoulder neckline, a wired V-neck bust, a fitted long sleeve, a high side slit on the floor-length hem, and a curve-hugging A-line silhouette. The long dress is composed of a lined velvet fabric that offers a moderate stretch. Complete the look with rhinestone heels and a sphere clutch. Fit & FeaturesOne-shoulder neckline, wired V-neck bust, Fitted long sleeve, High side slit, floor-length hem, A-line silhouette, Lined velvet fabric, Form-hugging fit, moderate stretch, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cheyenne Formal One-Shoulder Velvet Dress in Black | Size: S | Rhinestone/Velvet Fabric
Addison Glitter Mesh Formal Dress in Black
$29.97 $69.90
57% off
Make a sparkly statement at your next soiree in the trendy glam Addison glitter formal dress! Bring radiance to the room in this floor-length dress with a sleek design that fits like a glove. Fit & FeaturesSheer glitter mesh fabric, full knit stretchy lining, Sleeveless cowl neckline, spaghetti straps, High waist seam, Floor-length fitted silhouette, Runs true to size, Where to Wear:Prom, black tie weddings, galas, special date nights, rehearsal dinner Free Shipping on All Orders Over $75. | Windsor Addison Glitter Mesh Formal Dress in Black | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
Embellished with light-catching sequins, the Bethanie formal dress is a clear stunner with a lace-up back and a flattering mermaid silhouette with a floor-length hem. Fit & FeaturesSequin-scroll pattern, mesh fabric, stretch knit lining, Sleeveless V-neckline, padded bust, Lace-up back, zipper and hook-eye closure, Mermaid silhouette, Floor-length hem, Runs true to size, Where to Wear:Formal dances, black-tie events, formal weddings, and upscale parties. Free Shipping on All Orders Over $75. | Windsor Bethanie Formal Sequin V-Neck Mermaid Dress in Pink-2 | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
Look your best for a fancy night in the stunning Amirah formal glitter dress! Fashioned with an eye-catching cross back, this dress will make you feel like the star of the evening with a high slit and floor-length column silhouette. Fit & FeaturesGlitter knit fabric, moderate stretch, Sleeveless cowl neckline, Spaghetti straps, cross back, Side pleated seam, slim silhouette, high front slit, Floor-length column silhouette, Runs true to size, Extra glitter for maximum sparkle - may have some natural fallout, Where to Wear:Prom, black-tie weddings, galas, and upscale birthday events. Free Shipping on All Orders Over $75. | Windsor Amirah Formal Glitter Cowl Neck Column Dress in Green | Size: XS | Knit Fabric
The Rose formal long column dress is the perfect combination of elegance and glamour with a sheer corset trim and high-side slit for effortless allure! Fit & FeaturesMesh fabric, partial stretchy knit lining, Sleeveless sweetheart neckline, cowl pleating, Adjustable spaghetti straps, crisscross open back, Padded bust, sheer corset bodice, flexible boning, Side ruched seams, fitted column silhouette, High-side slit, floor-length hem, Style runs small, Where to Wear:Prom, weddings, bridesmaids, rehearsal dinners, cocktail soirees, and dressed-up date nights. Free Shipping on All Orders Over $75. | Windsor Rose Formal Mesh Corset Column Dress in Brown | Size: XS | Knit Fabric/Mesh Fabric
Dare to stun in the Jamie satin formal dress crafted with silky satin fabric for a gorgeous sheen. The bold plunge halter neckline and open lace-up back will turn heads while the fitted column silhouette flaunts your curves. Fit & FeaturesSilky satin fabric, short knit stretchy lining, Plunge halter V-neckline, shoulder straps, padded bra cups, Lace-up open back, lower zipper with hook-eye closure, High side slit, Fitted column silhouette, Floor-length hem, Runs true to size, Where to Wear:Prom, weddings, galas, and black-tie soirees. Free Shipping on All Orders Over $75. | Windsor Jamie Lace-Up Satin Formal Column Dress in Brown | Size: S | Knit Fabric/Satin Fabric
Designed to be eyed up and down, the Shayla long formal dress brings the sultry heat to any black-tie occasion! A curved neckline and sheer mesh lace corset bodice create a sophisticated silhouette, while the lace-up back provides a personalized fit. Fit & FeaturesSheer mesh, smooth knit fabric, Lace corset bodice, flexible boning, padded bra cups, Lace-up, back zipper with hook-eye closure, Floor-length fitted silhouette, high front wrap slit, Runs true to size, Where to Wear:Formal dances, black-tie galas, red-carpet occasions, and big birthday events, weddings, bridal showers, engagement parties, rehearsal dinners. Free Shipping on All Orders Over $75. | Windsor Shayla Strapless Corset Lace Formal Dress in Red | Size: S | Knit Fabric/Sheer Mesh 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.









