Date Night Outfits
Ready to turn heads and break hearts? Date night outfits are all about making a statement, and girl, we've got the looks that will have you feeling like the main character of your own rom-com. Whether you're going for that sultry allure or playful charm, our collection is packed with pieces that scream confidence and style. From flirty skirts to daring dresses and tops that tease just right, these outfits are your ticket to an unforgettable night out. Go ahead, Windsor girl—make every date night legendary!
$44.90
A red floral print mesh maxi dress with a sleeveless sweetheart neckline and bodycon silhouette.
$69.90
A black floor-length formal dress with a glitter mesh overlay and a cowl neckline.
$32.90
A chic pair of black high-rise skinny pants in coated faux leather with minimal stretch.
$32.90
A lime yellow mesh mini dress with a cowl neckline and adjustable spaghetti straps for a chic night.
$79.90
A white taffeta mini dress featuring a detachable bow with a dramatic train for stunning entrances.
$34.90 - $42.90
A black crepe halter jumpsuit with a plunging V-neckline and sexy midriff cutout.
$36.90
An elegant sage off-the-shoulder midi dress with a flared hem and smooth knit fabric.
$54.90
A beige bodycon mini dress featuring rhinestone mesh, square neckline, and trendy bell sleeves.
$79.90
A pink mini dress with faux pearl embellishments, cowl neckline, and strappy open-back design.
$52.90
A white mini bodycon dress with faux pearl embellishments, featuring a sweetheart neckline and ruched seams.
$18 $22.90 21% off
A sleek black faux leather mini skirt with a high waist, front slit, and hidden back zipper.
$32.90
A sage satin mini dress with an off-the-shoulder neckline and flattering A-line silhouette.
$39.90
A chic white glitter lace dress with a bodycon fit, perfect for weddings or special occasions.
$74.90
A navy blue glitter knit mermaid dress with a square neckline and lace-up open back.
$84.90
A strapless yellow bodycon mini dress with beaded mesh fabric and a cowl neckline.
$46 $64.90 29% off
A black crepe formal dress with puff sleeves, lace-up back, and high-cut slit for prom.
$49.90
A black faux leather and mesh jacket with illusion stripes, perfect for layering over chic outfits.
$36.90
A pink ribbed knit skater dress with an off-the-shoulder neckline and long fitted sleeves.
$69.90
A white bodycon mini dress adorned with iridescent rhinestones and faux pearl embellishments.
$36.90
A brown floral flocked bodysuit with a sweetheart neckline and adjustable straps in mesh knit fabric.
$29.97 $54.90 45% off
A wine-colored glitter-knit mini dress with a cowl neckline and flattering bodycon silhouette.
$48.90
A lavender mesh mini dress with faux pearl embellishments and adjustable spaghetti straps.
$39.90
An on-trend burgundy satin mini dress with ruched sides and sheer mesh balloon sleeves.
$9.97 $59.90 83% off
A shimmery black sequin party dress featuring a one-shoulder design and bodycon wrap silhouette.
$99.90
A mint sequin scroll mermaid dress with a strappy back, perfect for prom or black-tie events.
$19.97 $39.90 50% off
A green glitter mesh mini dress with sheer long sleeves and a flattering bodycon silhouette.
$9.97 $59.90 83% off
A striking green satin one-shoulder dress with a side slit, perfect for formal occasions.
$36.90
A wine-colored bodycon midi dress with a surplice V-neckline and elegant asymmetrical hem.
$29.97 $54.90 45% off
A burgundy formal dress with sheer mesh, bell sleeves, and a high-side slit for elegant occasions.
$34.90
A brown cargo mini skirt with a high-rise waist, vertical seams, and cargo-style pockets.
$79.90
A black knit mermaid dress with glitter, cowl neckline, and high slit for formal occasions.
$46.90
A vibrant yellow skater dress with a ruffled skirt, halter tie-back, and smocked high waist.
$9.97 $42.90 77% off
A glittery black mini dress with a one-shoulder balloon sleeve and front tie ruching.
$56.90
A black mesh mini dress with rhinestones, featuring a bodycon silhouette and sheer long sleeves.
$59.90
A black glitter knit bodycon dress with an off-the-shoulder neckline and high slit design.
$89.90
A dazzling orange bodycon dress with glitter polka dots, adjustable straps, and a lace-up back.
$29.90
A black crepe strapless bodycon dress with a pleated side seam and faux wrap skirt.
$39.90
A sheer white fishnet crop top adorned with mini rhinestones, perfect for standout style.
$9.97 $49.90 80% off
A red satin midi dress with a cowl neckline and side ruching for an elegant silhouette.
$59.90
A red bodycon mini dress with rhinestone embellishments, adjustable straps, and a slinky knit fabric.
$46.90
A stylish pair of medium denim high-rise straight cropped jeans with knee destruction and moderate stretch.
$44.90
A navy blue bodycon mini dress with rhinestone embellishments and a sheer mesh overlay.
$74.90
A burgundy satin formal dress featuring a cowl neckline, waist cutout, and thigh-high slit.
$59.90
A black glitter mesh bodycon mini dress with sheer ruffled sleeves and an open back.
$32.90
A sultry pink bustier top with lace trim, lined mesh, and adjustable spaghetti straps.
$54.90
A red bodycon mini dress with rhinestone and pearl embellishments, featuring a sweetheart neckline and adjustable straps.
$49.90
A strapless pink party dress featuring tulle ruffles and a bodycon silhouette in lined mesh fabric.
$46 $64.90 29% off
A dazzling white sequin party dress with a sweetheart neckline and adjustable spaghetti straps.
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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
Date Night Outfits
When it comes to curating the ultimate lineup of date night outfits, it’s all about dialing up the confidence and letting your personality do the talking. Whether you’re headed to a rooftop dinner, catching a late-night movie, or just out for spontaneous adventures with your crush, the right outfit can turn every moment into a main character memory. Think of your closet as the playground and each piece as your secret weapon—flirty dresses that twirl with every step, sleek jumpsuits that hug in all the right places, and tops that show just enough to keep them guessing. These aren’t just clothes; they’re your armor for unforgettable nights, your power move when you want to make an entrance, and your comfort zone when you’re laughing until you can’t breathe. And let’s be real, shopping for a windsor date night look is basically a love language in itself—whether you’re treating yourself or surprising your bestie with a “you have to wear this” pick. Gifting a killer date night outfit isn’t just about the fabric or fit; it’s about giving someone the confidence to own the night, to step into any room and know they’re that girl.
Picking the perfect date night outfit is all about striking that balance between effortless and unforgettable. You want to feel like you, just with a little extra sparkle. Start with what makes you feel unstoppable—maybe it’s a curve-hugging midi, a sassy mini, or a silky cami that catches the light just right. Don’t forget the details: a daring slit, a touch of lace, or a bold back cutout can turn a simple look into a total showstopper. Accessories are your best friend here, too—layered necklaces, statement earrings, or a clutch that’s just big enough for your lip gloss and phone. And if you’re the friend who’s always hyping up the group chat, you know the power of a great skirt. For those nights when jeans just won’t cut it, check out our curated selection of Date Night Skirts for inspo that’ll have you spinning on the dance floor and racking up compliments. The beauty of these pieces is how they flex to fit your vibe, whether you’re going for glam, casual-cute, or somewhere in between.
Date night isn’t just about impressing someone else—it’s your excuse to celebrate yourself, to dress up for the thrill of it, and to create moments you’ll replay in your head for weeks. The best part? These outfits work for every kind of rendezvous, from first dates to anniversaries, spontaneous meetups to planned escapes. They’re the go-to choice for anyone who wants to feel unstoppable, whether you’re single and ready to mingle or keeping the spark alive with your forever plus-one. And if you’re shopping for a gift, nothing says “I adore you” like an outfit that brings out someone’s inner goddess. With every piece designed to move with you—think breezy fabrics, dreamy draping, and silhouettes that flatter from every angle—you’ll be ready for whatever the night throws your way. So, grab your heels, cue your favorite playlist, and let your windsor date night look do the talking. Because when you feel amazing, the night is yours to own.