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!
$36.90
A pink ribbed knit skater dress with an off-the-shoulder neckline and long fitted sleeves.
$59.90
A sage satin formal dress with a square neckline, high slit, and floor-length hem.
$69.90
A black floor-length formal dress with a glitter mesh overlay and a cowl neckline.
$39.90
A chic pair of black high-rise skinny pants in coated faux leather with minimal stretch.
$39.90
A sultry black formal dress with rhinestone straps, cowl neckline, and a high slit.
$32.90
A lime yellow mesh mini dress with a cowl neckline and adjustable spaghetti straps for a chic night.
$79.90
A sleek black taffeta mini dress featuring a dramatic detachable bow with a floor-length train.
$36.90
An elegant sage off-the-shoulder midi dress with a flared hem and smooth knit fabric.
$34.90 - $42.90
A black crepe halter jumpsuit with a plunging V-neckline and sexy midriff cutout.
$79.90
A sage mini dress with faux pearl embellishments, featuring a cowl neckline and strappy open back.
$52.90
A white mini bodycon dress with faux pearl embellishments, featuring a sweetheart neckline and ruched seams.
$32.90
A sage satin mini dress with an off-the-shoulder neckline and flattering A-line silhouette.
$9.97 $22.90 56% off
A sleek black faux leather mini skirt with a high waist, front slit, and hidden back zipper.
$84.90
A strapless yellow bodycon mini dress with beaded mesh fabric and a cowl neckline.
$39.90
A chic white glitter lace bodycon dress with adjustable straps and an asymmetric hem.
$74.90
A navy blue glitter knit mermaid dress with a square neckline and lace-up open back.
$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.
$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.
$19.97 $54.90 64% off
A wine-colored glitter-knit mini dress with a cowl neckline and ruched bodycon silhouette.
$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.
$76.90
A black glitter mini dress with a strapless neckline, pleated design, and detachable bow train.
$99.90
A mint sequin scroll mermaid dress with a strappy back, perfect for prom or black-tie events.
$9.97 $59.90 83% off
A striking green satin one-shoulder dress with a side slit, perfect for formal occasions.
$79.90
A black knit mermaid dress with glitter, cowl neckline, and high slit for formal occasions.
$36.90
A wine-colored bodycon midi dress with a surplice V-neckline and elegant asymmetrical hem.
$34.90
A brown cargo mini skirt with a high-rise waist, vertical seams, and cargo-style pockets.
$19.97 $54.90 64% off
A burgundy formal dress with sheer mesh, bell sleeves, and a high-side slit for elegant occasions.
$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.
$29.97 $89.90 67% off
An orange bodycon dress with glitter polka dots, lace-up back, and adjustable spaghetti straps.
$39.90
A navy blue knit mini dress featuring a sleeveless V-neck, padded bust, and ruched bodycon silhouette.
$59.90
A red bodycon mini dress with rhinestone embellishments, adjustable straps, and a slinky knit fabric.
$29.90
A black crepe strapless bodycon dress with a pleated side seam and faux wrap skirt.
$9.97 $49.90 80% off
A red satin midi dress with a cowl neckline and side ruching for an elegant silhouette.
$54.90
A red bodycon mini dress with rhinestone and pearl embellishments, featuring a sweetheart neckline and adjustable straps.
$39.90
A sheer white fishnet crop top adorned with mini rhinestones, perfect for standout style.
$46.90
A stylish pair of medium denim high-rise straight cropped jeans with knee destruction and moderate stretch.
$49.90
A pink sleeveless bodycon mini dress with shimmering sequin embroidery and a stylish cutout back.
$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.
$46.90
A black floral midi dress with a corset bodice, sweetheart neckline, and flirty front slit.
$54.90
A black crepe glitter knit midi dress with a form-hugging silhouette and chic wrap hem.
$46 $64.90 29% off
A dazzling white sequin party dress with a sweetheart neckline and adjustable spaghetti straps.
$34.90
A black abstract floral mini dress featuring a cowl halter neckline and ruffled slit design.
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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: XL | 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 Red | Size: M | 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 Natural | Size: XS | Knit 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
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 Light Blue-2 | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
A fashionista like you will adore this basic mini skirt for creating your day and night looks! Featuring an elasticized high-rise waistband, bodycon silhouette, and a flirty front hem slit on stretchy and smooth knit fabric. Style with a corset top and heels. Fit & FeaturesHigh-rise elasticized waistband, Bodycon silhouette, Front hem slit, Mini-length hem, Stretchy and smooth knit fabric, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Get Down With Basic Slit Mini Skirt in Black | Size: XL | 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 Wine | Size: M | Knit Fabric/Mesh Fabric/Mesh Fabric
Both sexy and demure, the Kristen party dress wows from every angle! Perfect for bachelorette weekends, themed soirees, and formal birthdays! She features a sleeveless sweetheart neckline with a padded bust, cowl draping, adjustable spaghetti straps, and side ruched seams that hug your curves along her short bodycon silhouette. The formal party dress is composed of a faux pearl embellished mesh fabric with a stretchy knit lining. Complete the look in statement block heels. Fit & FeaturesSleeveless sweetheart neckline, Padded bust, cowl draping, Adjustable spaghetti straps, Side ruched seams, bodycon silhouette, Mini-length hem, Faux pearl embellishments, mesh fabric, stretch knit lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Kristen Faux Pearl Mini Party Dress in White | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
Date Night Outfits
When it comes to planning your next unforgettable night out, nothing sets the mood quite like finding the perfect date night outfit that feels as good as it looks. Whether you’re headed to rooftop drinks with that new Hinge match, catching a late-night movie with your forever crush, or dancing ‘til dawn with your ride-or-die crew, the right look is your secret weapon. The Windsor date night collection is all about helping you channel main character energy—think flirty skirts that twirl with every step, curve-hugging dresses that turn heads, and statement tops that know how to flirt back. The beauty of these pieces is how easily they adapt to your plans; a simple switch from sneakers to strappy heels, or a bold swipe of red lipstick, and suddenly you’re ready to take on anything the night throws your way. Dressing for date night isn’t just about what’s trending, it’s about wearing confidence like your favorite accessory and making sure your outfit keeps up with your plans (and your playlist).
Let’s be real: the best date night looks are the ones that feel like you. Maybe you’re all about a classic dress with a little black magic, or maybe you love a playful floral skirt paired with a cheeky crop top for that “oops, did I do that?” vibe. For casual hangs, nothing beats the effortless combo of a cute blouse and your favorite jeans—especially when you add a pair of statement earrings or a belt that cinches you in all the right places. If you’re leveling up for something a bit more formal, a sleek cocktail dress or a dramatic maxi brings instant glam, while boots or bold accessories keep things interesting. And don’t forget: comfort is key. The last thing you want to worry about is fussy straps or shoes that cut your night short. Instead, focus on pieces that move with you—think stretchy fabrics, adjustable details, and silhouettes that celebrate every curve. These aren’t just outfits; they’re confidence-boosters, conversation-starters, and memory-makers all rolled into one.
Date night outfits also make the sweetest gifts for your besties, your sister, or anyone who deserves a little extra sparkle. There’s something special about unwrapping a dress that’s just begging for a night out or slipping into a skirt that makes you want to spin in front of the mirror. If you’re looking for a sign to treat yourself (or someone you love) to a wardrobe refresh, this is it. And for those who love to keep their options open, don’t sleep on the power of a great skirt—it’s the ultimate mix-and-match piece, ready to take you from dinner to dancing and everywhere in between. For inspo on how to style your next statement piece, check out the curated picks on our Date Night Skirts page. No matter where the night takes you, Windsor has your back with looks that are as fearless and fun as you are.