Fall Casual Dresses
Hey there, autumn queen! 🍂 It's time to dive into the cozy-chic world of fall casual dresses that are ready to slay your seasonal style game. Whether you're crunching leaves underfoot or sipping on a pumpkin spice latte, these dresses are your ticket to effortless elegance with a dash of laid-back charm. Think warm hues, playful patterns, and silhouettes that hug you just right—perfect for everything from weekend brunches to spontaneous road trips. So go ahead, wrap yourself in the magic of fall, and let these dresses be your ultimate style sidekick.
$36.90
An elegant sage off-the-shoulder midi dress with a flared hem and smooth knit fabric.
$36.90
A chic black ribbed knit skater dress with an off-the-shoulder neckline and long fitted sleeves.
$39.90
A brown knit midi dress with long sleeves, off-the-shoulder neckline, and ruched bodycon fit.
$59.90
An effortlessly pretty chiffon midi dress with a floral print, ruffled tiers, and smocked details.
$44.90
A grey ribbed knit midi dress with a sweetheart neckline and twist accent, perfect for casual outings.
$42.90
A rust floral skater dress in breezy rayon with tie-back halter straps and an open back.
$19.97 $39.90 50% off
A khaki woven midi dress with a smocked bodice, square neckline, and ruffled A-line silhouette.
$44.90
A sultry black floral maxi dress with a V-neckline and form-hugging silhouette for vacations.
$46.90
An olive green gauze skater dress featuring flowy sleeves, V-necklines, and a chic cutout bodice.
$21.97 $42.90 49% off
An elegant brown ribbed knit mini dress with a scoop neckline and faux topper long sleeves.
$42.90
A blue paisley halter skater dress featuring a smocked bust, ruffled hem, and flowy woven fabric.
$59.90
An ivory A-line maxi dress with gauze fabric, sheer lace insets, and a faux leather belt.
$22.97 $49.90 54% off
A black woven mini dress with pleated A-line silhouette and spaghetti strap ties for casual outings.
$49.90
An olive green gauze skater dress featuring a tie-front, ruffled tiers, and adjustable spaghetti straps.
$29.90
A trendy brown striped knit mini dress with a mock neckline and long fitted sleeves.
$36.90
A cozy heather grey ribbed knit mini dress with an off-the-shoulder neckline and A-line silhouette.
$42.90
A rust paisley skater dress featuring a halter V-neckline, smocked bust, and playful tie-back design.
$25 $34.90 28% off
An elegant grey plaid mini dress with a strapless neckline and flirty pleated hem.
$54.90
A sleeveless denim maxi dress featuring a flowy ruffled silhouette and lightweight woven fabric.
$38.90
A burgundy knit skater dress featuring a cold-shoulder design and corset-style seams for stylish flair.
$69.90
A natural gauze midi dress featuring a strapless smocked bodice and cascading ruffled silhouette.
$59.90
A pink woven mini dress featuring a tie-front design, pleated hem, and spaghetti strap ties.
$29.90
A taupe ribbed knit bodycon mini dress with spaghetti straps and a scoop neckline for casual outings.
$44.90
An ethereal ivory chiffon skater dress featuring flirty ruffles and a strappy tie-back design.
$49.90
A strapless black woven midi dress featuring a color block bodice, flowy hem, and hidden pockets.
$36.90
A ribbed knit mini dress in raisin with a folded off-the-shoulder neckline and skater silhouette.
$9.97 $38.90 74% off
A wine-colored velvet mini dress with a sweetheart neckline, flare sleeves, and bodycon silhouette.
$42.90
A chartreuse ribbed knit midi dress featuring a strapless sweetheart neckline, keyhole cutout, and high slit.
$28.90
A black gauze midi dress featuring a flowy silhouette, V-neckline, adjustable straps, and hidden side pockets.
$26.90
A taupe plaid mini dress with a V-neckline, spaghetti straps, and a side slit.
$32.90
An ivory striped ribbed knit mini dress with an off-the-shoulder neckline and long fitted sleeves.
$42.90
A light blue gingham skater dress featuring a smocked waist, sweetheart neckline, and adjustable straps.
$44.90
A natural striped knit midi dress featuring a halter neckline, cutout bodice, and lace-up open back.
$36.90
A denim satin mini dress with a ruched wrap silhouette and spaghetti straps for a chic look.
$79.90
A black mini dress with faux pearl embellishments, featuring a strappy open-back and bodycon silhouette.
$38.90
A white sleeveless ribbed knit midi dress featuring a V-neckline and chic high front slit.
$42.90
A wine-colored mesh mini dress with a lace-up back and flattering bodycon silhouette.
$68.90
A chic mauve skater dress featuring floral jacquard satin, a corset bodice, and lace-up back.
$38.90
A white eyelet knit skater dress featuring a sleeveless square neckline and adjustable spaghetti straps.
$46.90
A black mesh maxi dress with a floral print, cowl neckline, and halter tie-back straps.
$44.90
A white floral skater dress with a strappy tie-back and ruffled mini-length hem.
$19.97 $59.90 67% off
An ivory mini dress with sheer mesh, faux pearl embroidery, and a cold-shoulder design.
$44.90
A breezy white chiffon skater dress featuring a cold-shoulder design, sweetheart neckline, and ruched bodice.
$49.90
A lavender skater dress with glitter mesh, sheer sleeves, and a fit and flare silhouette.
$46.90
A navy blue strapless mini skater dress in stretchy poplin with a ruched bodice and pleated hem.
$46.90
An ivory striped midi dress with cutouts, adjustable straps, and dual side slits for casual elegance.
$32.90
A breezy white eyelet knit skater dress featuring a square neckline and double-layered flared skirt.
$46.90
An adorable white eyelet mini dress with a flirty tie-back and ruffled A-line silhouette.
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Have a twirl-worthy moment in this gorgeous and glam satin skater dress. It features a sleeveless square neckline, adjustable spaghetti straps that lead to a cross-back and lace-up back design, a fitted bodice with a high waist, and a flirty skater silhouette. Style this dress with rhinestone earrings and new heels. Fit & FeaturesSleeveless, square neck, adjustable spaghetti straps, Built-in padded bust, Lace-up back design, Fitted bodice, high waist seam, Skater pleated silhouette, Satin fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor A Moment In Satin Skater Dress in Blue | Size: L | Rhinestone/Satin Fabric
Lustrous silk for your fancy needs. Show up to the celebration in this satin skater dress designed to fit and flatter every figure in a sleeveless cowl neckline, spaghetti straps, and a form-fitting bodice that leads to a short-length hem. Complete the look in fab block heels. Fit & FeaturesSleeveless cowl neckline, spaghetti straps, Form-fitting bodice, Skater style skirt, Short-length hem, Silky smooth satin fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Silky Chic Satin Skater Dress in Blue | Size: L | Satin Fabric
A chic staple skater dress featuring a flirty off-the-shoulder folded neckline and a short-length perfect for styling with boots or heels. Fit & FeaturesRibbed knit fabric with plenty of stretch, Off-the-shoulder neckline, fold-over accent, Long fitted sleeves, Short-length hem, Skater silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Staple Ribbed Knit Skater Dress in Pink | Size: S | Knit Fabric
Flirt up the room at your next dressy affair in this adorable skater dress designed with a floral jacquard satin fabric for a chic look. It features a sleeveless sweetheart neckline with ruching at the bust and a tie-front detail, a corset bodice with vertical seam detailing, a lace-up back design to create that snatched fit, a V-shaped drop waist, and a short skater skirt with an iconic fit-and-flare silhouette. Fit & FeaturesFloral jacquard satin fabric with lace-trim lining, Sweetheart neckline, ruched underwire bust, tie-front detail, Thin adjustable shoulder straps, lace-up back, Corset bodice with vertical seam detailing, flexible boning, V-shaped drop waist, Short skater skirt, fit-and-flare silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flirt It Up Floral Jacquard Satin Corset Skater Dress in Black | Size: S | Satin Fabric
Bling Fling Satin Rhinestone Skater Dress in Royal Blue
$9.97 $45.90
78% off
Show off a hint of bling in this satin skater dress for your next dressy soiree! Adorned with detachable rhinestone-embellished straps for a stunning sparkle, this dress will be the night's hit. The smooth satin-knit fabric offers plenty of stretch for comfortable wear. The short dress features a sleeveless square neckline, ruched side seams at the bodice, and a flattering fit-and-flare skater silhouette. Complete your look with rhinestone bow heels. Fit & FeaturesStretchy smooth satin-knit fabric, knit lining at the bust, Sleeveless square neckline, Detachable rhinestone-embellished thin straps, Side ruched seams at the bodice, High waist seam, Fit-and-flare skater silhouette, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Bling Fling Satin Rhinestone Skater Dress in Royal Blue | Size: XS | Knit Fabric/Rhinestone/Satin Fabric
Create a sweet summer look that is oh-so-darling with this drop-waist skater dress. Designed with a lightweight woven fabric, the bodice is accented with a dainty lace trim for a pretty vibe. The short dress features a sleeveless sweetheart neckline, a ruched bust with a small tie-front adjustable detail, and thin tank straps leading to an alluring lace-up back for a customized fit. The asymmetric drop-waist is detailed with pleated side panels, flowing down to a tiered A-line silhouette for a flirtatious look. Style with hoop earrings and a charm necklace. Fit & FeaturesWoven fabric with lace trim woven lining, Sweetheart neckline, ruched bust, adjustable tie-front, Tank straps, lace-up back design, Back zipper and hook-eye closure, Asymmetric drop-waist, pleated side panels, Tiered A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Darling Woven Drop-Waist Skater Dress in White | Size: XS | Woven Fabric
Short and sweet, this adorable floral skater dress will perfect your spring vibe. The lace-up corset bodice and V-shaped drop waist snatches your waist, while the flared A-line silhouette gives that flirty flair. Fit & FeaturesSmooth woven fabric with woven lining, sheer lace trims, no stretch, Sleeveless sweetheart neckline, underwire, ruched bust, tie-front detail, Thin adjustable shoulder straps, Corset bodice, structured boning, pleating, lace-up back, hidden zipper with hook-eye closure, V-shaped drop waist, Short skater silhouette, floral print, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Babe Corset Drop Waist Floral Skater Dress in Ivory | Size: XL | Sheer Lace Fabric/Woven Fabric
Be your own adorable muse in this sleeveless skater dress boasting a V-neckline and a ruffled skater silhouette. Complete the look with heels. Fit & FeaturesSheer lace fabric with knit lining, plenty of stretch, V-neckline with twist-front bust design, Adjustable spaghetti straps, V-shaped drop waist, Mini-length tiered ruffled skater silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Adorable Muse Ruffled Lace Skater Dress in Sage | Size: XS | Lace Fabric/Knit Fabric/Sheer Lace Fabric
Capture hearts with your sweet look in this airy eyelet knit skater dress. You'll adore the flowy feel of the fit-and-flare silhouette. Fit & FeaturesEyelet knit fabric with knit lining, Sleeveless square neckline, underbust seam, Adjustable spaghetti straps, Skater silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Look Eyelet Knit Skater Dress in White | Size: S | Knit Fabric
Flirty And Adorable Strapless Lace Bow Floral Skater Dress in Natural
$26.97 $59.90
55% off
Flirty and adorable, this floral skater dress makes the sweetest impression at showers or birthdays! Featuring a sweetheart neckline with delicate lace trim and a charming bow, this dress is sure to turn heads. The padded bra cups provide a perfect fit, while the skater silhouette and mini-length hem add a touch of playfulness. Complete the look with earrings and strappy heels. Fit & FeaturesFloral print, chiffon fabric lined with woven, Strapless sweetheart neckline, Lace trim and bow, Padded bra cups, Back zipper and hook-eye closure, Skater silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flirty And Adorable Strapless Lace Bow Floral Skater Dress in Natural | Size: M | Chiffon
Fall Casual Dresses
When it comes to curating the ultimate lineup of fall casual dresses, it’s all about embracing those effortlessly cool vibes that make every day feel like a main character moment. Picture this: you’re gliding into your favorite coffee spot, the air is crisp, and you’re rocking a casual dress that hugs you just right—soft fabrics, playful details, and that perfect balance of cozy and chic. Whether you’re headed to brunch with your ride-or-die crew, scoping out the cutest pumpkin patch photo ops, or just living your best life on a spontaneous road trip, a closet full of windsor casual dresses means you’re always ready to slay the day (and the group chat). These dresses aren’t just about looking good—they’re about feeling unstoppable, moving through your world with confidence, and turning the sidewalk into your own personal runway. And let’s be real, nothing says “I’ve got this” quite like a dress that lets you twirl, lounge, and conquer all at once.
Gift-giving? Oh, you’re about to win “Best Gift Giver” in the group chat. Casual fall dresses make the ultimate surprise for your BFF, your sister, or that friend who always borrows your clothes and never gives them back (we see you, girl). They’re the kind of gift that says, “I know your style, and I want you to feel amazing every single day.” Think about it: a dress that’s easy to throw on, works for everything from last-minute dates to family dinners, and looks just as good with sneakers as it does with boots. That’s the kind of wardrobe hero every girl needs. And if you’re shopping for yourself—hello, self-love!—you already know that nothing beats the thrill of unboxing a new dress that’s about to become your go-to for every “what should I wear?” moment. From soft knits that feel like a hug to playful prints that spark all the compliments, casual dresses for autumn are basically your ticket to being the best dressed, wherever you go.
When you’re ready to step up your style game, think of fall casual dresses as your secret weapon. These are the pieces that make getting dressed a breeze, letting you mix and match with jackets, cardis, and all your fave accessories. Whether you’re layering up for a late-night bonfire or keeping it simple for a chill day out, these dresses are designed to keep up with every plan (even the ones you make five minutes before leaving the house). The best part? With Windsor’s range of styles, you’ll always find something that fits your mood—flirty, fierce, or just flat-out comfy. If you’re looking to expand your wardrobe with even more must-have looks, check out our Fall Season Dresses for endless inspo and all the dreamy details. Every day’s a chance to own your style, and with the right casual dress, you’re already halfway there.