Fall Season Dresses
Falling leaves, pumpkin spice, and cozy vibes—it's that magical time of year when your wardrobe gets a chic autumn upgrade. Fall season dresses are here to sweep you off your feet with their irresistible charm and flair. Whether you're twirling through a crisp afternoon or making a statement at a seasonal soirée, these dresses are your ultimate partners in crime. From rich hues to playful patterns, each piece is designed to make you feel like the unstoppable force you are. So go ahead, embrace the season's best styles and strut into fall with confidence! 🍂✨
$38.90
An olive green maxi dress featuring a low back with tie, cowl neckline, and stretchy knit fabric.
$36.90
A denim satin mini dress with a ruched wrap silhouette and spaghetti straps for a chic look.
$46.90
A black mesh maxi dress with a floral print, cowl neckline, and halter tie-back straps.
$19.97 $34.90 43% off
An off-white abstract mini dress featuring a one-shoulder neckline and a 70s-inspired sheer sleeve.
$36.90
An elegant sage off-the-shoulder midi dress with a bodycon fit and flared hem.
$36.90
A chic pink skater dress with a ribbed knit, off-the-shoulder neckline, and long fitted sleeves.
$26.90
A charcoal bodycon mini dress with a mock neck and fitted long sleeves in cotton-blend knit.
$39.90
A brown knit midi dress with long sleeves, off-the-shoulder neckline, and ruched bodycon fit.
$42.90
A rust floral skater dress in airy rayon with tie-back halter straps and an open back.
$46.90
An olive green gauze skater dress featuring V-neck cutouts, flowy sleeves, and a breezy silhouette.
$49.90
An olive green gauze skater dress featuring a tie-front, ruffled tiers, and adjustable spaghetti straps.
$9.97 $46.90 79% off
A taupe bodycon mini dress with a flocked velvet floral pattern and chic cold-shoulder design.
$36.90
A cozy heather grey ribbed knit mini dress with an off-the-shoulder neckline and A-line silhouette.
$49.90 - $52.90
A black linen skater dress featuring a sweetheart neckline, lace-up back, and flexible boning.
$29.90
A trendy brown striped knit mini dress with a mock neckline and long fitted sleeves.
$42.90
An olive green paisley skater dress featuring a halter V-neckline, smocked bust, and playful ruffled hem.
$38.90
A burgundy knit skater dress featuring a cold-shoulder design and corset-style seams for a sleek look.
$25 $34.90 28% off
An elegant grey plaid mini dress with a strapless neckline and flirty pleated hem.
$9.97 $54.90 82% off
A wine velvet mini dress with a ruched bodycon silhouette and adjustable spaghetti straps.
$44.90
A strapless burgundy mesh maxi dress featuring a bold floral print and a dramatic high side slit.
$9.97 $38.90 74% off
A wine velvet mini dress with a sweetheart neckline, flare sleeves, and bodycon silhouette.
$34.90
A plum floral midi dress with a strapless neckline and front slit in knit fabric.
$44.90
A navy blue rib knit sweater dress with contrast trim, square neckline, and a flared pleated hem.
$36.90
A ribbed knit mini dress in raisin with a folded off-the-shoulder neckline and skater silhouette.
$35.90
A burgundy plaid mini dress with lace trim, spaghetti straps, and a form-hugging silhouette.
$45.90
A natural floral mesh midi dress featuring a strapless neckline, bodycon silhouette, and sultry back slit.
$54.90
An ivory floral chiffon skater dress featuring sheer long sleeves, a sweetheart neckline, and button accents.
$59.90
A stunning sage bodycon mini dress with sequin embroidery, halter straps, and an open lace-up back.
$79.90
A black mini dress with faux pearl embellishments, featuring a cowl neckline and open-back design.
$46.90
A black glitter crepe knit mini dress with sheer mesh sleeves and a daring bodycon silhouette.
$42.90
A wine-colored mesh mini dress with a lace-up back and flattering bodycon silhouette.
$48.90
An elegant black off-the-shoulder midi dress with ruched sides and a flattering bodycon fit.
$9.97 $42.90 77% off
A grey glitter knit mini dress with a one-shoulder neckline and ruched side seams.
$69.90
A chic black bodycon dress featuring a low back and ruffled bubble hem for elegant occasions.
$35.90
A sassy red-brown bodycon mini dress with a one-shoulder neckline and soft hacci knit fabric.
$59.90
A black mini dress with sheer mesh, faux pearl embroidery, and a cold-shoulder design.
$24.97 $69.90 64% off
A stunning orange satin mermaid dress featuring a lace-up back and elegant wrap silhouette.
$42.90
A black ponte mini dress with sheer chiffon sleeves and a playful square neckline.
$24.97 $59.90 58% off
A sultry orange strapless bodycon dress with ruched mesh fabric and a center back slit.
$64.90
A luxe black velvet skater dress with an off-the-shoulder neckline and pleated drop-waist design.
$24.97 $49.90 50% off
An elegant orange mermaid dress featuring a cowl neckline and adjustable spaghetti straps in stretchy knit.
$36.90
A green mini-length bodycon dress featuring a pleated sweetheart bust and open back with criss-cross straps.
$69.90
A black flocked floral velvet skater dress with a sweetheart neckline and flirty spaghetti tie straps.
$9.97 $42.90 77% off
A slate A-line mini dress with a V-neckline and ruffled hem in soft knit fabric.
$9.97 $44.90 78% off
A black velvet floral mini dress with sheer sleeves and a sweetheart neckline for holiday events.
$44.90
A pink lace skater dress featuring ruffled shoulder straps, a sweetheart neckline, and a lace-up back.
$42.90
An abstract print maxi dress with a ruched bodycon silhouette and sheer off-the-shoulder sleeves.
$21.97 $42.90 49% off
An elegant brown ribbed knit mini dress with a scoop neckline and faux topper long sleeves.

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Fall Season Dresses
When you’re on the hunt for a dress that brings all the cozy vibes with a side of main character energy, you know Windsor fall dresses are about to serve. Think of slipping into something that makes you want to twirl through crunchy leaves, grab a latte with your ride-or-die crew, or snap a pic at golden hour because, honestly, you look that good. Fall is that sweet spot where you can layer up without hiding your style, and every dress becomes a canvas for your signature boots, that jacket you love, or a hat that instantly upgrades your outfit. Whether you’re headed to a late-night bonfire, brunching with your besties, or just want to turn heads at your next group hang, these dresses are your go-to for feeling confident and put together—no matter what your calendar has in store. And let’s be real: if you’re shopping for someone else, Windsor fall dresses are the ultimate “I saw this and thought of you” surprise. Whether it’s for a birthday, a just-because treat, or a little pick-me-up for your BFF, a dreamy dress that fits her vibe is always a win.
Picking out the perfect fall dress is all about knowing your own mood and the moments you want to own. Maybe you’re the first one on the dance floor at every party, or maybe you’re more about those chill nights in with your favorite people and a killer playlist. Either way, you want a dress that moves with you—think flowy skirts that catch the breeze, fitted silhouettes that hug you in all the right places, and details like smocked bodices, puff sleeves, or a pop of lace that make you feel like the main event. Don’t sleep on the power of a good print, either. From moody florals to classic plaids, the right pattern can set your whole mood for the day. And if you’re gifting? Just imagine your bestie’s face lighting up when she unwraps a dress that feels like it was made for her. It’s the kind of gift that says “I know you” in the best way, and gives her a reason to plan her next big adventure—or at least a cute photo op.
When it comes to styling, Windsor fall dresses are basically your blank slate for endless outfit inspo. Layer up with a denim jacket for those breezy evenings, throw on some knee-high boots for instant drama, or keep it simple with sneakers and a crossbody bag for a look that’s equal parts comfy and cool. The best part? These dresses are made for mixing it up, so you can go from daytime hangs to night-out plans without missing a beat. And if you’ve got a special event on your radar—think homecoming, a family gathering, or a date that’s got your heart racing—make sure to check out the full lineup of Fall Occasion Dresses for styles that are ready to steal the spotlight. No matter where you’re headed or who you’re shopping for, Windsor’s got your back with looks that are as fearless and fun as you are.