Fall Date Night Dresses
Get ready to turn heads and steal hearts with our irresistible collection of fall date night dresses! Whether you're planning a cozy dinner by the fireplace or a starry evening stroll, these outfits will have you feeling like the main character in your own romantic movie. Dive into rich autumn hues, playful patterns, and chic silhouettes that scream confidence and charm. With every twirl, you'll be serving up the perfect blend of warmth and style, making sure every moment is as unforgettable as you are. So go ahead, Windsor girl—dress to impress and let those fall date nights become legendary tales of fashion and fun!
$46.90
A brown woven midi dress with a ditsy floral pattern, corset bodice, and high front slit.
$36.90
A denim satin mini dress with a ruched wrap silhouette and spaghetti straps for a chic look.
$59.90
A royal blue sequin bodycon mini dress with adjustable straps and a lace-up open back.
$69.90
A black floor-length formal dress featuring a glitter mesh fabric, cowl neckline, and spaghetti straps.
$32.90
A chic wine-colored strapless mini dress with pleated bust and flowy A-line silhouette.
$32.90
A pink mesh mini dress with a cowl neckline and adjustable spaghetti straps for a chic night out.
$84.90
A strapless black bodycon mini dress with beaded mesh fabric and a cowl neckline.
$69.90
A white bodycon mini dress featuring rhinestones and faux pearls for a glamorous, sultry look.
$89.90
A dazzling periwinkle party dress featuring sequin lace-mesh fabric and a flirty lace-up back.
$19.97 $54.90 64% off
A wine-colored glitter-knit mini dress with a cowl neckline and flattering bodycon silhouette.
$42.90
A wine-colored mesh mini dress with a lace-up back and flattering bodycon silhouette.
$15.97 $54.90 71% off
A burgundy formal dress with sheer mesh sleeves, high slit, and curve-hugging silhouette.
$46.90
This skater dress was made for sunset happy hours this season! It features a sleeveless V-neckline, halter tie-back straps, an open back, a stretchy smocked high waist, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The lightweight twill fabric includes a woven lining. Style this short dress with espadrille sandals and a mini handbag. Fit & FeaturesSleeveless V-neckline, Halter tie-back straps, open back, Stretchy smocked high waist, Short skater skirt, tiered ruffled design, Fit and flare silhouette, Twill fabric, woven lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sunset Happy Hour Ruffled Skater Dress in Yellow | Size: S
$9.97 $42.90 77% off
A glittery black mini dress with a one-shoulder balloon sleeve and front tie ruching.
$9.97 $49.90 80% off
A red satin midi dress with a cowl neckline and side ruching for an elegant silhouette.
$56.90
A black mesh mini dress with rhinestones, featuring a bodycon silhouette and sheer long sleeves.
$54.90
A red mini dress with rhinestone and pearl embellishments, featuring a sweetheart neckline and bodycon fit.
$48.90
An elegant black off-the-shoulder midi dress with ruched sides and a flattering bodycon fit.
$19.97 $64.90 69% off
A black taffeta skater dress with a low back bow and elegant square neckline.
$69.90
An elegant white bodycon dress featuring a low back and charming ruffled bubble hem.
$39.90
A pink glitter knit mini dress with a sweetheart neckline and flirty A-line silhouette.
$54.90
A navy blue floral satin dress with a strappy lace-up back and flirty A-line silhouette.
$35.90
A white knit bodycon midi dress featuring a square neckline, spaghetti straps, and side ruched seams.
$42.90
A black ponte mini dress with sheer chiffon sleeves and a playful square neckline.
$9.97 $42.90 77% off
A grey glitter knit mini dress with a one-shoulder neckline and ruched side seams.
$89.90
An ivory floral mini dress featuring delicate beading, mesh fabric, and a strapless cowl neckline.
$49.90
A black sheer midi dress with off-the-shoulder neckline, plunging v-neck, and high-side slit.
$44.90
A white mesh bodycon mini dress with faux pearl embellishments and adjustable spaghetti straps.
$49.90
A lavender skater dress with glitter mesh, sheer sleeves, and a fit and flare silhouette.
$49.90
A dark marsala chiffon mini dress featuring a sweetheart neckline, twist bust, and ruffled hem.
$9.97 $42.90 77% off
A berry-colored strapless knit midi dress with a cowl neckline and asymmetric hem for sultry allure.
$44.90
A black floral maxi dress featuring sheer mesh, a lace-up strappy back, and a form-hugging silhouette.
$34.90
A sage satin mini dress featuring a strapless pleated neckline and flattering A-line silhouette.
$64.90
An elegant black velvet skater dress with an off-the-shoulder neckline and drop-waist design.
$84.90
A white mesh mini dress featuring floral beaded embellishments, cutout back, and a curve-hugging bodycon fit.
$32.90
A black mini bodycon dress with a sweetheart neckline and dramatic ruched bell sleeves.
$29.97 $59.90 50% off
A black lace bodycon mini dress featuring faux pearl embellishments and adjustable spaghetti straps.
$22.97 $49.90 54% off
A black bodycon mini dress with a lace-up back, pearl and rhinestone embellishments, and front slit.
$11.97 $52.90 77% off
A black sequin mini dress featuring a halter V-neckline and a flirty open back design.
$42.90
A wine-colored mini dress featuring a sheen knit fabric, halter square neckline, and bodycon silhouette.
$9.97 $42.90 77% off
A black velvet mini dress with an asymmetric one-shoulder neckline and ruched bodycon silhouette.
$79.90
A black glitter formal dress with a strappy open back, high front slit, and mermaid silhouette.
$54.90
A strapless black sequin mini dress with a bodycon silhouette, perfect for celebrations.
$42.90
A strapless black knit mini dress featuring a form-hugging silhouette and playful ruffled hem.
$39.90
A burgundy glitter knit mini dress with a sultry open back and ruched bodycon fit.
$9.97 $59.90 83% off
A chic black lace mini dress with a sweetheart neckline, feather trim, and sheer long sleeves.
$44.90
A chic black short dress with sheer mesh sleeves and a sleek satin A-line silhouette.
$35.90
A red sheen knit mini dress featuring a cutout bust, sweetheart neckline, and flattering A-line silhouette.
Now Trending
Windsor Carmen Off-The-Shoulder Long Sleeve Column Dress in Black
$19.97 $64.90
69% off
Channel an elegant moment in the Carmen long column dress that features an off-the-shoulder neckline, a draped ruched bodice, and fitted long sleeves. Complete the look with rhinestone earrings for the perfect wedding guest outfit. Fit & FeaturesSmooth knit fabric, short knit lining, moderate stretch, Off-the-shoulder fold-over neckline, Ruched bodice, Fitted long sleeves, Long-length hem, Column silhouette, Runs true to size, Where to Wear:Weddings, rooftop parties, dressed-up dinners, and romantic date nights. Free Shipping on All Orders Over $75. | Windsor Carmen Off-The-Shoulder Long Sleeve Column Dress in Black | Size: S | Knit Fabric/Rhinestone
Fall Date Night Dresses
When it comes to setting the mood for a date night, nothing works magic quite like the perfect dress. Whether you’re plotting a candlelit rooftop dinner, a spontaneous drive out to the city lights, or just want to make your regular spot feel like the most romantic place in town, the right dress is your secret weapon. It’s that little boost of confidence that turns butterflies into fireworks, and trust—when you slip into a look that makes you feel unstoppable, your energy is absolutely contagious. Windsor fall dresses are all about those moments when you want to look like you didn’t try too hard (even though you totally did), with luxe touches and dreamy details that make every entrance unforgettable. Think rich hues that glow under golden hour, flirty silhouettes that move with you, and textures that beg for a little extra attention—because date night is all about the details, and you deserve to be the main character.
Choosing a dress for a fall date night isn’t just about the outfit—it’s about telling your story. Maybe you’re getting ready for a first date and want something that says “fun, fearless, and totally unforgettable,” or maybe you’re celebrating an anniversary and want to dial up the romance with something a little extra. These dresses are made for every vibe: soft and flowy for the girls who love a little drama in their twirls, bodycon and bold for the ones who want to own the spotlight, and everything in between for those “just right” moments. They’re also the ultimate pick-me-up gift, whether you’re treating your bestie to a surprise girls’ night or dropping hints for your own wish list (because who says you can’t gift yourself?). Each dress is designed with real life in mind—think adjustable straps for that custom fit, playful necklines that show just enough, and fabrics that feel as good as they look. The best part? You don’t have to choose between comfort and style. These dresses are made to keep up with every laugh, every dance, and every late-night adventure, no matter where the night takes you.
Let’s be real: fall date nights are a whole mood, and your wardrobe should match that energy. Picture yourself strolling through downtown with a hot chocolate in hand, wrapped up in a dress that turns heads with every step. Or maybe you’re cozied up in a booth, sharing secrets and sweet potato fries, feeling like you’re in your own romantic movie montage. Windsor fall dresses are crafted for those unforgettable moments—the ones you’ll be talking about in the group chat for weeks. And if you’re looking to turn up the glam for something extra special, check out the latest selection of Fall Evening Dresses for even more inspiration. No matter how you style it, you’re guaranteed to serve looks, steal hearts, and make every date night one for the books. So go ahead, dress like the main character—because you never know when your next epic love story is about to begin.