Winter Date Dresses
Winter date dresses are here to keep you cozy and chic, even when the temperature drops! Whether you're headed for a romantic dinner under twinkling lights or a spontaneous ice-skating adventure, these dresses have your back. Think soft fabrics, flattering silhouettes, and just the right amount of sparkle to make those winter nights unforgettable. So grab your favorite boots and get ready to slay every date night with confidence and style. Because why should the cold have all the fun?
$109.90
A chic navy blue mermaid dress with sequins, a square neckline, and a thigh-high slit.
$54.90
A stunning red mesh corset dress with a sweetheart neckline, crisscross back, and high side slit.
$19.97 $54.90 64% off
An enchanting orange satin gown with a cowl neck, high slit, and sleek spaghetti straps.
$59.90
A navy blue satin midi dress with a pleated cowl neckline and a high side slit.
$79.90
A light blue mini dress with faux pearl embellishments, featuring a cowl neckline and open-back design.
$21.97 $47.90 54% off
A lustrous green satin skater dress with a cowl neckline and spaghetti straps for elegant occasions.
$32.90
A sage satin off-the-shoulder mini dress with a flattering A-line silhouette for special occasions.
$54.90
A green satin midi dress with a corset seam bodice and pleated faux wrap hem.
$39.90
An on-trend burgundy satin mini dress with sheer balloon sleeves and a flattering bodycon silhouette.
$69.90
A periwinkle mesh off-the-shoulder dress with ruched seams and a mermaid silhouette for elegance.
$19.97 $39.90 50% off
A green glitter mesh bodycon dress with sheer long sleeves and a square neckline.
$29.97 $54.90 45% off
A burgundy formal dress with sheer mesh sleeves, high slit, and curve-hugging silhouette.
$46.90
A black glitter crepe knit mini dress with sheer bell sleeves and a bodycon silhouette.
$9.97 $49.90 80% off
A red satin midi dress with a cowl neckline, side ruching, and a high slit.
$44.90
A navy blue bodycon mini dress with rhinestone embellishments and a sheer mesh overlay.
$59.90
A black glitter mesh mini dress with sheer ruffled sleeves and a bodycon silhouette.
$39.90
A brown knit midi dress with long sleeves, off-the-shoulder neckline, and ruched bodycon fit.
$48.90
An elegant black off-the-shoulder midi dress with ruched sides and a flattering bodycon fit.
$23.97 $52.90 55% off
A black floral mesh midi dress featuring a ruffle trim sweetheart neckline and adjustable spaghetti straps.
$19.97 $44.90 56% off
A strapless black skater dress with lace corset bodice and chiffon ruffled silhouette.
$9.97 $59.90 83% off
A chic black velvet formal dress featuring an off-the-shoulder neckline and high side slit.
$49.90
A lavender glitter skater dress with sheer peasant sleeves and a fit and flare silhouette.
$42.90
A natural floral print bodycon midi dress with a lace-up back and flirty side slit.
$9.97 $42.90 77% off
A green glitter knit mini dress with an off-the-shoulder neckline and fitted long sleeves.
$64.90
A luxe black velvet skater dress with an off-the-shoulder neckline and pleated drop-waist design.
$42.90
A black ponte mini dress with sheer chiffon sleeves and a playful square neckline.
$49.90
A black sheer mesh midi dress with off-the-shoulder neckline and high-side slit for elegant occasions.
$9.97 $39.90 75% off
A black mini dress with a cutout bust, ruched wrap design, and sheer mesh long sleeves.
$44.90
A green off-the-shoulder glitter mini dress featuring a bodycon silhouette and sheer mesh fabric.
$79.90
A black glitter mermaid dress with a lace-up back and sweetheart halter neckline.
$59.90
A green velvet mini dress with sequin embroidery and a striking lace-up back design.
$32.90
A black bodycon mini dress with ruched mesh bell sleeves and a sweetheart neckline.
$42.90
A black velvet mini dress featuring an asymmetric one-shoulder neckline and ruched bodycon silhouette.
$44.90
A grey ribbed knit midi dress featuring a sweetheart neckline with a twist accent and long sleeves.
$44.90
A white mesh bodycon mini dress with faux pearl embellishments and adjustable spaghetti straps.
$22.97 $49.90 54% off
A pink floral sequin mini dress with a bustier bodice and adjustable spaghetti straps.
$9.97 $59.90 83% off
A black glitter midi dress with sheer sleeves, bodycon fit, and a ruched slit detail.
$36.90
A taupe midi dress with a sleeveless square neckline, ruching, and abstract marble print.
$36.90
A black glitter knit mini dress with an off-the-shoulder neckline and flirty A-line silhouette.
$32.90
A chic red sleeveless midi dress with ruched seams and a curve-hugging bodycon silhouette.
$9.97 $54.90 82% off
A red velvet mini dress with a cowl neckline and striking open-back design.
$59.90
A black lace bodycon mini dress with faux pearl embellishments and adjustable spaghetti straps.
$44.90
A chic black short dress with sheer mesh sleeves, satin body, and alluring back cutout.
$9.97 $44.90 78% off
A black velvet floral mini dress with sheer sleeves and a sweetheart neckline for holiday events.
$39.97 $79.90 50% off
A romantic black satin formal dress with a corset bodice and detachable statement bow.
$39.90
A burgundy glitter knit mini dress with a sultry open back and ruched bodycon fit.
$69.90
A burgundy satin mini dress with a corset bodice, applique design, and adjustable spaghetti straps.
$9.97 $39.90 75% off
A black mini dress with floral velvet burnout, sheer sleeves, and an open lace-up back.
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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
Shine bright and sparkle up the night in the gorgeous Leila mini dress. The dress boasts an alluring open back with a lace-up strappy design for a customized fit, and a short, curve-hugging silhouette. Shop Long Version: Kailani Formal Sequin Slit Mermaid DressFit & FeaturesSheer mesh fabric, full knit lining, moderate stretch, Sequin embroidery, scroll pattern, Sleeveless square neckline, adjustable spaghetti straps, Open back, lace-up strappy design, tie closure, High waist seam, lower back zipper, hook and eye closure, Mini-length hem, fitted bodycon silhouette, Runs true to size, Where to Wear:Prom, bachelorettes, birthdays, Vegas weekends, date nights Free Shipping on All Orders Over $75. | Windsor Leila Sequin Bodycon Mini Dress in Royal Blue | Size: L | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
Look and feel like a sultry senorita in this mesh mini dress perfect for an chic night on the town! It features a sleeveless cowl neckline, dual adjustable spaghetti straps with a tie-neck closure, and side and back ruched seams designed to flaunt your curves along the bodycon silhouette. Complete the look with hoop earrings. Fit & FeaturesSleeveless cowl neckline, Dual adjustable spaghetti straps, tie-neck closure, Side and back ruched seams, Back zipper and hook-eye closure, Bodycon silhouette, mini-length hem, Mesh fabric, brushed soft knit stretchy lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Senorita Mesh Strappy Mini Dress in Pink | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
Bring on the cute attitude in this ponte mini skort brings featuring a flattering high-rise waist, and a skirt overlay designed with dual front slits along the form-hugging fit. Fit & FeaturesSmooth ponte knit fabric, minimal stretch, High-rise waist, Skirt overlay, dual front slits, Form-hugging silhouette, Mini-length hem, Shorts lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cute Attitude Ponte Slit Mini Skort in Black | Size: XL | Knit Fabric
Show up and stun this formal season in the gorgeous Brynlee bodycon mini dress! She features a sleeveless square neckline, a built-in padded bust, halter spaghetti straps, an open back with a lace-up design for a customized fit, and a short, curve-hugging silhouette. The lined mesh fabric features all-over sequin embroidery in an intricate scroll pattern. Style the formal mini dress with clear heels for a night to remember. Fit & FeaturesSleeveless, square neckline, Built-in padded bust, no bra required, Halter spaghetti straps, back button closure, Open back, lace-up design, zipper closure, Bodycon silhouette, mini-length hem, Sequin scroll embroidery, mesh fabric, knit lining, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Brynlee Sequin Embroidered Bodycon Dress in Sage | Size: S | Knit Fabric/Mesh Fabric/Mesh Fabric
Every occasion is worth celebrating in this off-the-shoulder midi dress! The smooth and stretchy knit fabric includes a full-length knit lining for additional coverage. The off-the-shoulder neckline and short-sleeve cuffs add a touch of elegance, while the bodycon silhouette and flared midi-length hem accentuate your curves in all the right places. Complete the look with teardrop earrings and heels. Fit & FeaturesSmooth stretchy knit fabric with knit lining, Off-the-shoulder neckline, Short-sleeve cuffs, Bodycon fit, Flare hem, Style runs small, Free Shipping on All Orders Over $75. | Windsor Exceptional Off-The-Shoulder Flared Midi Dress in Black-2 | Size: XL | Knit Fabric
Bring the dazzling glamour to the party in this long sleeve rhinestone mesh mini dress! Designed with a stretchy sheer mesh fabric with a partial knit lining, the mini-length dress is accented with all-over rhinestone embellishments for a gorgeous and chic shine. The square neckline shapes the bodice, and the unlined long sleeves have slit accents and flare out for a trendy look. The bodycon silhouette will hug your gorgeous curves. Style this mini dress with rhinestone heels for all the more sparkle. Fit & FeaturesStretchy sheer mesh fabric, partial knit lining, Rhinestone embellishments, Square neckline, Long bell sleeves with slit detail, Back zipper, hook and eye closure, Bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Dazzling Glam Long Sleeve Rhinestone Mesh Mini Dress in Beige | Size: XL | Knit Fabric/Rhinestone/Mesh Fabric
A mini dress that brings the luxe sensation! The Keira faux pearl short dress is a stunning style with a strappy tie-back design and a bodycon silhouette that highlights your figure. Fit & FeaturesLightweight mesh fabric, stretchy knit lining, Faux pearl and bead embellishments, Sleeveless cowl neckline, Spaghetti straps, strappy tie-back design, open-back, Bodycon silhouette, mini-length hem, Runs true to size, Where to Wear:Prom, birthday parties, bachelorettes, Vegas weekends, rooftop cocktails Free Shipping on All Orders Over $75. | Windsor Keira Faux Pearl Strappy Open-Back Mini Dress in Pink | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
The first step is picking the right dress. You're going to be working it in this figure-hugging mini! Put your hair in a half-up-do and slip into some heels for a bomb AF look! The dress features a sleeveless cowl neckline, spaghetti straps that cross at the back, and an asymmetrical hem. Complete the outfit with sleek hoop earrings. Fit & FeaturesSleeveless drapey cowl neckline, Spaghetti straps, cross at back, Mini length, asymmetric hemline , Smooth knit fabric, metallic sheen , Form-hugging fit , Plenty of stretch , Runs true to size, Free Shipping on All Orders Over $75. | Windsor All The Right Moves Cowl Neck Mini Dress in Green | Size: S | Knit Fabric
Everyone will see you shining at the club in this glitter mini dress! It features an off-the-shoulder sweetheart neckline, sheer fitted ruched long sleeves, adjustable spaghetti straps, a ruched seam along the padded bust, a sheer bodice with trim, and side ruched seams that hug your curves on the bodycon silhouette. Complete the look with a clutch and heels. Fit & FeaturesOff-the-shoulder sweetheart neckline, Adjustable spaghetti straps, Sheer fitted ruched long sleeves, Ruched and padded bust, sheer bodice, trim, Side ruched seams, bodycon silhouette, mini-length hem, Glitter mesh fabric, sewn-in knit lining, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor See Me Shining Glitter Off-The-Shoulder Mini Dress in Navy Blue | Size: L | Knit Fabric/Mesh Fabric/Mesh Fabric
Winter Date Dresses
When it comes to planning a romantic night out or a spontaneous dinner for two, winter date dresses are the secret weapon every Windsor girl needs in her closet. Picture this: you’re stepping out into the crisp evening air, feeling that little shiver of excitement (okay, and maybe a tiny chill), but your look is so on point, you know you’ll be the main character all night. A winter date dress isn’t just about looking cute—it’s about feeling unstoppable, whether you’re headed to a candlelit restaurant, a rooftop with twinkling lights, or a cozy movie marathon at home. The right dress hugs you in all the right places, keeps you feeling warm (but never overheated), and makes sure your confidence is the only thing that’s truly fire. Think luxe velvet that catches the light with every move, sultry long sleeves that add a dash of mystery, and unexpected details—like a daring back cutout or a flirty slit—that turn heads without even trying. Whether you’re celebrating something special or just making any ordinary night feel extraordinary, the perfect winter date dress is like your best friend hyping you up before you even leave the house.
Choosing a winter date dress is all about balancing that cozy, snuggly vibe with just the right amount of “I woke up like this” glam. You want something that feels soft and luxe against your skin, but still lets you move, dance, and laugh without a care. For the girl who loves to keep things classic, a fitted knit dress with a high neckline and long sleeves brings the drama while still being totally wearable. If you’re feeling bold, a bodycon with a little shimmer or a playful print is the move—especially when paired with boots and your go-to statement coat. And for those moments when you want to keep it low-key but still look like you tried (even if you just rolled out of bed), there’s nothing like slipping into a casual dress that’s both effortless and totally date-night approved. Winter date dresses also make the sweetest gifts—think besties, sisters, or anyone who deserves a little extra sparkle in their life. Wrapping up a dreamy dress with a handwritten note? That’s the kind of thoughtful surprise that makes memories. And if you’re the one doing the shopping, don’t be afraid to treat yourself. You deserve to feel gorgeous, no matter what your plans look like.
From first dates that make your heart race to anniversaries that feel like a fairy tale, winter date dresses are made for moments you’ll want to remember. Imagine twirling in the middle of a crowded dance floor, or sharing secrets over dessert—your dress should be as unforgettable as the night itself. Layer with tights or a faux fur jacket if you’re braving the elements, or keep it simple and let your dress do all the talking. The best part? There’s a style for every mood, every vibe, and every adventure. And if you’re craving something a little more laid-back for those casual nights in, don’t forget to check out our Winter Casual Dresses for even more inspo. No matter where the night takes you, Windsor has your back—because you deserve to feel like the main event, every single time.