Date Night Midi Dresses
Ready to turn heads and steal hearts? Date night midi dresses are here to make sure you’re the center of attention, whether it's a candlelit dinner or a spontaneous adventure. These dresses strike the perfect balance between flirty and sophisticated, giving you that effortlessly chic vibe. From sultry slits to playful prints, each piece whispers confidence and promises an unforgettable evening. So go ahead, slip into something fabulous and let your style do all the talking—because tonight is all about you, gorgeous!
$44.90
A sophisticated white midi dress featuring sheer chiffon sleeves and a sultry ruched bodycon silhouette.
$35.90
A pink sleeveless bodycon midi dress crafted from stretchy knit fabric with a square neckline.
$46.90
A burgundy bodycon midi dress featuring floral lace texture, a square neckline, and a daring front slit.
$46.90
A sage green knit midi dress featuring a cowl halter neckline, pleated bust, and ruched bodycon silhouette.
$69.90
A black floor-length formal dress with a glitter mesh fabric and a cowl neckline.
$59.90
A navy blue satin wrap midi dress with a cowl neckline and adjustable spaghetti straps.
$36.90
An elegant black off-the-shoulder midi dress with a bodycon fit and flared hem in stretchy knit.
$29.97 $59.90 50% off
A navy blue satin midi dress with a pleated cowl neckline and high side slit.
$38.90
A black sleeveless ribbed knit midi dress with a V-neckline and chic high front slit.
$54.90
An ivory satin midi dress with a corset seam bodice and pleated faux wrap hem.
$44.90
A black mesh bodycon midi dress with a high neck, ruffled hem, and elegant ruching.
$36.90
A wine-colored bodycon midi dress with a surplice V-neckline and spaghetti straps for elegant occasions.
$39.90
A sultry black one-shoulder bodycon midi dress crafted from smooth, stretchy double-lined knit fabric.
$20.97 $46.90 55% off
A black floral midi dress with a corset bodice, sweetheart neckline, and flirty front slit.
$48.90
An elegant black off-the-shoulder midi dress with ruched sides and a flattering bodycon fit.
$54.90
A chic black midi dress with a glitter knit fabric, featuring a wrap hem and flirty slit.
$46.90
A black bodycon midi dress with a square neckline, crafted from stretchy double-lined knit fabric.
$35.90
A white knit bodycon midi dress featuring a square neckline, spaghetti straps, and side ruched seams.
$45.90
An elegant white satin midi dress with a strapless cowl neckline and form-hugging fit.
$39.90
A captivating black floral mesh maxi dress with a lace-up back and flared hem.
$36.90
A mauve knit midi dress with a sleeveless square neckline and pleated mermaid silhouette.
$35.90
A strapless rose midi dress in smooth, stretchy knit fabric with padded cups and a bodycon silhouette.
$59.90
A chic navy blue midi dress with glitter knit fabric, sweetheart neckline, and lace-up back.
$19.97 $28.90 31% off
A breezy black midi dress featuring gauze fabric, a V-neck, adjustable straps, and hidden side pockets.
$44.90
A black mesh midi dress with a floral flocked velvet pattern and a high side slit.
$59.90
A green satin midi dress featuring a cowl neckline, pleated bodice, high side slit, and twist-back detail.
$9.97 $49.90 80% off
An elegant black mesh midi dress with ruched sides, sheer sleeves, and a tiered ruffled hem.
$42.90
A vibrant orange knit midi dress featuring a halter neckline, side cutouts, and a flattering bodycon fit.
$9.97 $59.90 83% off
A black glitter midi dress with sheer sleeves, bodycon fit, and a ruched slit detail.
$39.90
A sultry black bodycon midi dress featuring a floral velvet burnout texture and lace-trimmed neckline.
$59.90
A chic navy blue satin midi dress featuring a strapless bodycon fit and elegant wrap front slit.
$42.90
A sleek green knit midi dress featuring a strapless sweetheart neckline, pleated overlay, and back slit.
$36.90
A sleek black knit midi dress with a halter neckline and flared mermaid silhouette.
$19.97 $59.90 67% off
A sage satin midi dress featuring a lace-trimmed bust, keyhole cutout, and high front slit.
$48.90
A grey floral mesh midi dress featuring a V-notch neckline, ruched bust, and bodycon silhouette.
$34.90
A strapless red brown knit midi dress featuring side ruching, bodycon silhouette, and a chic side slit.
$42.90
A strapless burgundy midi dress in sleek knit fabric, featuring a pleated bust and sultry back slit.
$34.90
A sage mesh midi dress featuring a cowl neckline, ruched sides, and adjustable tie-back straps.
$49.90
An off-the-shoulder black midi dress featuring mesh-lined fabric, ruched bodycon silhouette, and a bold side slit.
$49.90
A pink floral mesh bodycon midi dress featuring off-the-shoulder sleeves, ruching, and a sweetheart neckline.
$54.90
An ivory satin midi dress with a lace-up back, front wrap slit, and adjustable straps.
$39.90
A sleek black knit midi dress featuring a ruched bodycon silhouette, sleeveless V-neckline, and spaghetti straps.
$46.90
A white stretch lace midi dress featuring a low back, sheer hem, and flirty side slit.
$54.90
An alluring black velvet-patterned midi dress with a flirty bust cutout and ruffled hem.
$52.90
A pink floral mesh midi dress featuring a strapless sweetheart neckline and ruched bodycon silhouette.
$39.90
A brown knit tube midi dress featuring a form-hugging silhouette and a dramatic ruffled hem.
$52.90
A black knit bodycon midi dress featuring lace trim, flirty cutouts, and a high side slit.
$49.90
A wine-colored knit midi dress featuring a low open back, statement bow, and ruffled hem.
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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: S | 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
Get all wrapped up in this stylish sleek satin mini dress. Dance the night away at that upcoming wedding or celebrate a girl's night in this statement dress that will have all eyes on you. The dress features a sleeveless square neckline, spaghetti straps, and a ruched wrap silhouette that hugs curves in all the right places. The mini-length dress is composed of a satin-like fabric that offers a moderate stretch. Complete your look with rhinestone earrings and strappy heels. Fit & FeaturesSleeveless square neckline, spaghetti straps, Strapless bra recommended, Ruched wrap-front detail , Mini-length bodycon silhouette , Satin-like fabric, sheen finish, Form-hugging fit, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Wrapped In Stylish Satin Mini Dress in Denim | Size: XS | Rhinestone/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
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
This adorable strapless A-line mini dress is so your vibe! Designed with a stretchy lined knit fabric, it features a strapless straight-across neckline, chic pleated detailing at the bust, and a flirty flowy A-line silhouette on the mini-length hem. Style for a girl's night with statement earrings and strappy mules. Fit & FeaturesStretchy knit fabric with knit lining, Strapless straight neckline, no-slip strip, Pleated bust, A-line fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Your Vibe Strapless A-line Mini Dress in Navy Blue | Size: L | Knit 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
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 Lime Yellow | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
Date Night Midi Dresses
When it comes to leveling up your date night game, nothing says “main character energy” quite like slipping into a date night midi dress that hugs you in all the right places and moves with your every step. There’s something about that midi length—the perfect in-between that lets you show off a little leg while keeping things irresistibly chic. Whether you’re headed out for rooftop cocktails, a candlelit dinner, or a spontaneous late-night adventure, a midi dress for dinner date moments always delivers. From sultry bodycons that turn heads to flowy silhouettes that float with every laugh, these dresses are all about giving you that instant confidence boost and making you feel unstoppable. The Windsor date night collection is a curated playground for every vibe, whether you’re channeling classic romance or ready to flirt with a little edge. And let’s be real: a date night midi dress isn’t just for romantic rendezvous. It’s for girls’ nights out, solo self-love dinners, or those “just because” evenings when you want to remind yourself how good it feels to dress up and show up.
If you’re new to the midi obsession and find yourself wondering what is a midi dress, you’re about to get schooled in the best way possible. Midi dresses typically hit anywhere from just below the knee to mid-calf, striking that sweet spot between flirty and sophisticated. They’re the ultimate go-to for those moments when you want to look effortlessly put-together without even trying. The magic of a midi is its versatility—dress it up with strappy heels and a killer clutch for a night out, or keep it chill with sneakers and a denim jacket for a more laid-back vibe. And if you’re shopping for someone else (hello, bestie birthday or just-because treat), a midi is a total crowd-pleaser. It flatters every body shape, works for every style personality, and transitions from dinner to dancing without missing a beat. Plus, if you’re the type who loves a little extra comfort, there’s nothing better than slipping into a sleep dress midi that feels like a dream but looks like you planned every detail. Think silky fabrics, dreamy fits, and just enough drama to keep things interesting.
No matter your plans, owning a lineup of date night midi dresses is basically a rite of passage for anyone who loves to make an entrance. These dresses are built for those unforgettable nights—when you’re laughing until your cheeks hurt, catching your reflection in a window and thinking, “Damn, I look good,” or twirling under city lights with your favorite person. And if you find yourself craving even more inspo for those after-dark moments, don’t miss out on exploring our Evening Midi Dresses collection for all the glam, glitz, and jaw-dropping styles your heart desires. Whatever the occasion, Windsor’s got your back, ready to hype you up and help you turn every date night into an epic story worth telling.