First Date Dresses
First date dresses are your secret weapon for making that unforgettable first impression. Whether you’re aiming for flirty and fun or effortlessly chic, it’s all about feeling confident and turning heads the moment you walk in. Your perfect match? A dress that brings out your best self and lets your personality shine. So go ahead, channel main character energy—because tonight, you’re not just going on a date, you’re making memories he’ll never forget.
$109.90
A chic navy blue mermaid dress with sequins, featuring a lace-up back and thigh-high slit.
$89.90
A sage satin formal dress featuring a pleated cowl neckline, empire waist, and high front slit.
$36.90
A denim satin mini dress with a ruched wrap silhouette and sleeveless square neckline.
$42.90
A sleek sage midi dress with a cowl neckline, spaghetti straps, and a chic high front slit.
$59.90
A dazzling royal blue mini dress featuring sequin embroidery and an alluring lace-up open back.
$69.90
A black floor-length formal dress with a glitter mesh overlay and a cowl neckline.
$39.90
A sultry black formal dress with rhinestone straps, cowl neckline, and a high slit.
$32.90
A chic denim strapless A-line mini dress with pleated bust and stretchy knit fabric.
$32.90
A lime yellow mesh mini dress with a cowl neckline and adjustable spaghetti straps.
$79.90
A sleek black taffeta mini dress featuring a dramatic detachable bow with a floor-grazing train.
$36.90
An elegant natural off-the-shoulder midi dress with a stretchy knit fabric and flared hem.
$49.90
A black crepe formal dress with a sleeveless square neckline and a high-cut front slit.
$54.90
A lavender mesh corset column dress featuring a sweetheart neckline and high-side slit for elegance.
$59.90
A stunning sage bodycon mini dress with sequin embroidery, halter straps, and an open lace-up back.
$14.97 $54.90 73% off
An elegant orange satin dress 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.
$52.90
A white mini bodycon dress with faux pearl embellishments, featuring a sweetheart neckline and ruched seams.
$32.90
An elegant white satin mini dress with an off-the-shoulder neckline and flattering A-line silhouette.
$84.90
A white strapless bodycon mini dress with beaded mesh fabric, perfect for modern brides or formal events.
$39.90
A chic white glitter lace bodycon dress with adjustable straps and an asymmetric hem.
$42.90
A wine satin mini dress with rhinestone straps, ruched seams, and a form-hugging silhouette.
$77 $109.90 30% off
A green sequin scroll dress with a plunging V-neckline and open lace-up back.
$74.90
A navy blue glitter knit mermaid dress with a square neckline and lace-up open back.
$69.90
A white bodycon mini dress with iridescent rhinestones and faux pearl embellishments on sheer mesh.
$38.90
A charming white A-line dress with a sweetheart neckline and adjustable spaghetti straps.
$89.90
A dazzling periwinkle sequin lace party dress featuring a lace-up back and skater silhouette.
$54.90
A wine-colored satin midi dress with a corset seam bodice and pleated faux wrap hem.
$42.90
A wine-colored mesh mini dress with a lace-up back and flattering bodycon silhouette.
$39.90
An on-trend burgundy satin mini dress with sheer puff sleeves and a flattering bodycon silhouette.
$36.90
A wine-colored knit bodycon midi dress with a surplice V-neckline and spaghetti straps.
$109.90
A stunning black sequin dress with a lace-up back, sweetheart neckline, and high front slit.
$59.90
A sleek black knit mermaid dress featuring a cowl neck, lace-up back, and high front slit.
$9.97 $59.90 83% off
A striking green satin one-shoulder dress with a side slit, perfect for formal occasions.
$59.90
A mauve floral mesh mermaid dress with a lace-up back, high slit, and floor-length hem.
$54.90
A chic black formal dress with sheer mesh sleeves, high slit, and curve-hugging silhouette.
$69.90
A periwinkle mesh off-the-shoulder dress with ruched seams and a mermaid silhouette.
$56.90
A black mesh mini dress with rhinestones, featuring a bodycon silhouette and sheer long sleeves.
$29.97 $89.90 67% off
An orange bodycon dress with glitter polka dots, lace-up back, and adjustable spaghetti straps.
$46.90
A black glitter crepe knit mini dress with sheer bell sleeves and a bodycon silhouette.
$39.90
A navy blue knit mini dress featuring a V-neck, spaghetti straps, padded bust, and ruched sides.
$59.90
A sleek green formal dress with a cowl neckline, front cutout, and high side slit.
$74.90
An elegant red glitter knit mermaid dress with an off-the-shoulder neckline and high front slit.
$38.90
A red knit mini dress with a sleeveless square neckline, pleated bust, and A-line silhouette.
$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 neon orange sequin mini dress with a lace-up back and bodycon fit for stunning curves.
$99.90
A light blue floral jacquard skater dress featuring a corset bodice, metallic threading, and hidden pockets.
$46 $64.90 29% off
A black taffeta skater dress featuring a low back bow and elegant square neckline.
$42.90
A sultry pink strapless mesh mini dress with ruffle trim and bodycon silhouette for standout style.
Now Trending
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 Navy Blue | Size: L | 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
First Date Dresses
First dates are basically the opening scene of your own rom-com—cue the butterflies, the playlist of flirty pop songs, and that one outfit that makes you feel like you could conquer the world (or at least the local rooftop bar). Picking out a first date dress is all about channeling that main character energy. Whether you’re meeting someone new over coffee, brunching at a cute café, or heading out for a spontaneous adventure, your dress is your secret weapon. It’s not just about looking good (which, let’s be real, you absolutely will), but about feeling unstoppable and comfortable in your own skin. Think soft, flowy fabrics that move with you, or a curve-hugging silhouette that turns heads the second you walk in. Maybe you’re the girl who loves a classic little black dress with a swipe of gloss, or maybe you’re all about bold colors and playful prints that show off your vibe before you even say hello. Either way, the right first date dress is like your own personal hype squad—there to remind you that you’re magnetic, unforgettable, and totally in control.
Shopping for a first date dress is basically an act of self-love—because you deserve to feel amazing, no matter where the night takes you. If you’re gifting a dress to your bestie before her big night (because you know she’s been spiraling over what to wear), or treating yourself to something new because you’re overdue for a confidence boost, these picks are made for moments that matter. Go for a style that’s versatile enough to handle last-minute plans—think dresses that can be dressed up with heels or down with sneakers, so you’re ready for everything from rooftop drinks to late-night pizza runs. And don’t forget the little details: adjustable straps, pockets (a total game-changer), and breathable fabric that keeps you cool even when your heart is racing. The best first date dresses are the ones that let you be yourself, whether you’re cracking jokes, dancing under the stars, or just owning the room with your smile. If you’re looking to turn up the elegance for a fancier night out, you can always explore more glam options in the Elegant Date Night Dresses collection for that extra wow factor.
Every Windsor girl knows that a first date dress isn’t just for dates—it’s the dress you reach for when you want to feel a little extra, even if you’re just hanging with friends or treating yourself to solo adventures. It’s about celebrating your individuality, making memories, and stepping into every moment with confidence. Whether you’re twirling on the sidewalk, laughing until your sides hurt, or making a new connection, your dress is there to back you up—like your ride-or-die bestie, always ready to hype you up and remind you that you’re absolutely killing it. So go ahead, pick the dress that feels like you, and get ready to create your own unforgettable story.