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.
$56.90
A black mesh mini dress with rhinestones, featuring a bodycon silhouette and sheer long sleeves.
$39.90
A burgundy glitter knit mini dress with a sultry open back and ruched bodycon fit.
$69.90
A black floor-length formal dress with a glitter mesh fabric and a chic cowl neckline.
$32.90
A pink mesh mini dress with a cowl neckline and adjustable spaghetti straps for a chic night out.
$84.90
A strapless sage mini dress with beaded mesh fabric and a flattering bodycon fit.
$69.90
A white bodycon mini dress featuring rhinestones and faux pearls for a glamorous, sultry look.
$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.
$54.90
A navy blue mini dress with rhinestone and pearl embellishments, featuring a sweetheart neckline and bodycon silhouette.
$69.90
An elegant white bodycon dress featuring a low back and charming ruffled bubble hem.
$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.
$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.
$49.90
A lavender skater dress with glitter mesh, sheer sleeves, and a fit and flare silhouette.
$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.
$19.97 $79.90 75% off
A royal blue glitter formal dress featuring a strappy open back and high front slit.
$32.90
A black mini bodycon dress with a sweetheart neckline and dramatic ruched bell sleeves.
$39.90
A sultry black lace bodycon mini dress with a sheer bodice and ruffled hem.
$59.90
A white lace mini dress with faux pearl embellishments and adjustable spaghetti straps for elegant outings.
$42.90
A strapless black knit mini dress featuring a form-hugging silhouette and playful ruffled hem.
$44.90
A chic black short dress with sheer mesh sleeves and a sleek satin A-line silhouette.
$9.97 $59.90 83% off
A chic black lace mini dress with a sweetheart neckline, feather trim, and sheer long sleeves.
$9.97 $74.90 87% off
An off-the-shoulder black velvet mini dress with rhinestone embellishments and a sheer mesh bodice.
$36.90
A heather grey knit mini dress with an off-the-shoulder neckline and A-line silhouette.
$38.90
An olive green maxi dress featuring a low back with tie, cowl neckline, and stretchy knit fabric.
$42.90
A black glitter mini dress with off-the-shoulder neckline, sheer sleeves, and ruching details.
$42.90
A berry velvet mini dress featuring a bold flocked cheetah print and sleek one-shoulder bodycon silhouette.
$49.90
An off-the-shoulder black midi dress featuring mesh-lined fabric, ruched bodycon silhouette, and a bold side slit.
$34.90
A sage mesh midi dress featuring a cowl neckline, ruched sides, and adjustable tie-back straps.
$54.90
An alluring black velvet-patterned midi dress with a flirty bust cutout and ruffled hem.
$9.97 $44.90 78% off
A black velvet glitter mini dress with a one-shoulder neckline and wrap-around waist cutout.
$39.90
A sleek black knit midi dress featuring a ruched bodycon silhouette, sleeveless V-neckline, and spaghetti straps.
$109.90
A romantic pink mermaid dress featuring floral sequins, a lace-up back, and spaghetti straps.
$21 $29.90 30% off
A chic charcoal plaid mini dress with sheer lace trims and a flattering bodycon silhouette.
$39.90
A black mesh-lined skater mini dress featuring a plunging V-neckline, open back, and ruffled hem.
$9.97 $39.90 75% off
A black glitter knit midi dress with a cowl neckline and mermaid silhouette for formal occasions.
$36.90
A sultry brown knit midi dress featuring a lace-up back, ruched bodycon fit, and side slit.
$46.90
A black knit halter mini dress featuring lace trim, ruffled tiers, and a dramatic cowl neckline.
$52.90
A chic black mini dress with an off-the-shoulder neckline and flared A-line silhouette.
$39.90
A wine-colored knit bodycon midi dress featuring a sweetheart neckline, bust detail, and sleek silhouette.
$59.90
A black sequin skater dress with an open back and tie-back bow, perfect for parties.
$9.97 $46.90 79% off
A sultry black mesh mini dress featuring a V-neckline, side sash, and bodycon fit.
$25 $34.90 28% off
A grey plaid strapless mini dress with a pleated hem and form-hugging knit fabric.
$9.97 $38.90 74% off
A wine-colored velvet mini dress with a sweetheart neckline, flare sleeves, and bodycon silhouette.
$45.90
A natural floral mesh midi dress featuring a strapless neckline, bodycon silhouette, and sultry back slit.
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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 Sage | Size: S | 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: XS | Rhinestone
The Marissa long satin dress brings elegance and sultriness to your formal night. The floor-length gown enhances your curves with a fitted bodice and flattering A-line silhouette while the high front slit provides movement. Fit & FeaturesStretch-satin fabric, non-see-through, double-lined bust, Sleeveless pleated cowl neckline, spaghetti straps, Slim-fit bodice, empire waistline, High front slit, floor-length hem, A-line silhouette, Runs true to size, Where to Wear:Prom, weddings, black-tie soirees, special date nights, and engagement parties. Free Shipping on All Orders Over $75. | Windsor Marissa Formal Satin Cowl Neck Dress in Green | Size: S | Satin Fabric
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-2 | Size: S | Rhinestone/Velvet Fabric
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:Prom, black-tie events, formal weddings, and upscale parties. Free Shipping on All Orders Over $75. | Windsor Bethanie Formal Sequin V-Neck Mermaid Dress in Yellow | Size: S | Knit Fabric/Mesh Fabric/Mesh Fabric
Sultry and stunning, the Alisha formal dress will keep all eyes on you. With thin rhinestone detailed straps that give effortless sparkle and a curve-hugging silhouette, and an alluring high slit. Fit & FeaturesLightweight, breathable stretchy fabric, Sleeveless cowl neckline, Rhinestone detailed straps, High waist seam, Floor-length hem, form-fitting silhouette, high slit, Runs true to size, Where to Wear:Prom, glamorous evenings, dinner parties, weddings Free Shipping on All Orders Over $75. | Windsor Alisha Rhinestone Strap Formal Dress in Black | Size: L | Stretchy Fabric/Rhinestone
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 Red | Size: XS | Knit Fabric/Satin 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 Green | Size: M | Knit Fabric/Mesh Fabric
Fall Date Night Dresses
When the air turns crisp and the city lights start to twinkle a little earlier, there’s just something about a night out that feels extra magical. Whether you’re headed to an intimate dinner, a rooftop rendezvous, or a cozy movie marathon, choosing the right date night dress is all about capturing that perfect balance of comfort, confidence, and a little bit of main character energy. Windsor fall dresses are designed to keep up with your every move—from spontaneous detours for late-night dessert to impromptu dance breaks under the stars. Think luxe fabrics that feel like a warm hug, silhouettes that hug in all the right places, and details that turn heads (and maybe spark a little envy in the best way). Shopping for a dress that makes you feel like the best version of yourself is always a win, whether you’re planning a night to remember with your crush, your crew, or yourself. And let’s be real, a killer date night dress isn’t just for romance—it’s for every moment you want to make unforgettable.
Gift shopping for your bestie, sister, or that friend who’s always down for an adventure? Date night dresses make an iconic gift—think of it as giving her a ticket to her next “wow, I look good” moment. Maybe she’s got a big anniversary coming up, or she’s finally saying yes to that long-awaited first date. Maybe she just deserves a little something special because she’s been killing it lately. Whatever the reason, wrapping up a gorgeous Windsor fall dress is like sending a little confidence boost in a box. And if you’re the one treating yourself (as you should), take a cue from the girls who know: it’s about more than just looking cute. It’s about feeling unstoppable, whether you’re sipping cocktails at your favorite spot or twirling through a night out with your ride-or-die. These dresses are made for mixing, matching, layering, and living your best life—no matter where the night takes you.
When you’re scrolling for the one, pay attention to those little details that make a big difference—think adjustable straps for the perfect fit, flirty necklines that frame your favorite necklace, or sleeves that keep you cozy without hiding your sparkle. Don’t be afraid to play with color or texture; rich jewel tones, plush velvets, and sleek satins are practically begging for a night out. And if your plans might involve a little more dancing and a little less sitting pretty, you’ll want a dress that moves with you—trust, nothing kills the vibe like a wardrobe malfunction mid-spin. For those who live for the dance floor, you’ll find even more inspo on our Fall Dance Dresses page, packed with styles that are ready to make every step count. No matter your style or your story, there’s a dress waiting to help you make memories—and maybe steal a few hearts along the way.