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!
$35.90
A pink sleeveless bodycon midi dress crafted from stretchy knit fabric with a square neckline.
$32.90
A brown sleeveless midi dress in smooth knit fabric with ruched seams and a bodycon silhouette.
$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.
$59.90
A black satin midi dress with a pleated cowl neckline, midriff cutout, 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.
$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.
$33.90
A light blue strapless bodycon midi dress crafted from rib knit fabric with a side slit detail.
$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.
$39.90
A sultry black bodycon midi dress featuring a floral velvet burnout texture and lace-trimmed neckline.
$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.
$44.90
A black midi dress with a floral flocked velvet pattern, halter neckline, and high side slit.
$42.90
A vibrant orange knit midi dress featuring a halter neckline, side cutouts, and a flattering bodycon fit.
$59.90
A green satin midi dress featuring a cowl neckline, pleated bodice, high side slit, and twist-back detail.
$34.90
A strapless red brown knit midi dress featuring side ruching, bodycon silhouette, and a chic side slit.
$9.97 $49.90 80% off
An elegant black mesh midi dress with ruched sides, sheer sleeves, and a tiered ruffled hem.
$39.90
A burgundy knit midi dress featuring a one-shoulder neckline, bow trim, and flared hem.
$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.
$19.97 $59.90 67% off
A sage satin midi dress featuring a lace-trimmed bust, keyhole cutout, and high front slit.
$49.90
A wine-colored knit midi dress featuring a low open back, statement bow, and ruffled hem.
$36.90
A sleek black knit midi dress with a halter neckline and flared mermaid silhouette.
$52.90
A pink floral mesh midi dress featuring a strapless sweetheart neckline and ruched bodycon silhouette.
$39.90
An ivory ribbed knit midi dress featuring a strapless neckline, side ruching, and a bodycon silhouette.
$42.90
A slinky brown knit midi dress featuring a boat neckline, open tie-back, and form-hugging silhouette.
$42.90
A strapless burgundy midi dress in sleek knit fabric, featuring a pleated bust and sultry back slit.
$49.90
An off-the-shoulder black midi dress featuring mesh-lined fabric, ruched bodycon silhouette, and a bold side slit.
$34.90
A sage mesh midi dress featuring a cowl neckline, ruched sides, and adjustable tie-back straps.
$54.90
An alluring black velvet-patterned midi dress with a flirty bust cutout and ruffled hem.
$36.90
A sultry brown knit midi dress featuring a lace-up back, ruched bodycon fit, and side slit.
$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 ivory satin midi dress with a lace-up back, front wrap slit, and adjustable straps.
$32.90
A romantic rust floral mesh midi dress featuring a strapless tube neckline and curve-hugging bodycon silhouette.
$52.90
A black knit bodycon midi dress featuring lace trim, flirty cutouts, and a high side slit.
$64.90
A brown satin bodycon midi dress featuring a sweetheart neckline, lace-up back, and front slit.
$36.90
A navy blue strapless midi dress in stretch knit with side waist cutouts and a bodycon silhouette.
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Achieve a perfectly stylish everyday look with this sleeveless ribbed knit midi dress! Designed with a comfortable ribbed knit fabric offering plenty of stretch, it features a V-neckline, spaghetti straps, a midi-length hem with a chic high front slit, and a form-hugging silhouette. Pair with a cropped denim jacket and clear mules. Fit & FeaturesStretchy ribbed knit fabric, V-neckline, Spaghetti straps, High front slit, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Perfectly Stylish Sleeveless Ribbed Knit Midi Dress in Black | Size: M | Knit Fabric
Channel the chic fall vibe in this ditsy floral woven midi dress featuring a sleeveless sweetheart neckline with a ruched bust and tie-front detail, thin tank shoulder straps, and a corset-style bodice. The high waist leads to a flowy A-line silhouette accented with a high-cut front slit. Fit & FeaturesDitsy floral-printed woven fabric, Sweetheart neckline, ruched bust, tie-front detail, underwire bust, Thin tank shoulder straps, Corset-style bodice with piping, high waist seam, Hidden side zipper and hook-eye closure, High front slit, Midi-length A-line fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Fall Vibe Ditsy Floral Corset Midi Dress in Brown | Size: S | Woven Fabric
Windsor Thriving Blooms Corset Floral Slit Midi Dress in Black
$20.97 $46.90
55% off
Thrive with sweet energy in this floral midi dress perfect for brunches or dates! With a corset bodice that snatches your waist and a flirty front slit, this a-line dress will captive everyone. Pair with a necklace. Fit & FeaturesDitsy floral print, woven fabric, Wide shoulder straps, sweetheart neckline, Corset bodice, Side pockets, A-line silhouette, front slit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Thriving Blooms Corset Floral Slit Midi Dress in Black | Size: S | Woven Fabric
Capture hearts with your sweet look in this airy eyelet knit skater dress. You'll adore the flowy feel of the fit-and-flare silhouette. Fit & FeaturesEyelet knit fabric with knit lining, Sleeveless square neckline, underbust seam, Adjustable spaghetti straps, Skater silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Look Eyelet Knit Skater Dress in White | Size: M | Knit Fabric
Create a cute picturesque 'fit in this corset A-line midi dress! The corset bodice and lace-up back add a touch of allure to the sweet silhouette. Fit & FeaturesWoven fabric lined with stretchy knit, Sweetheart neckline, tie-front detail, Thin adjustable straps, Corset bodice, lace-up back, High waist seam, Midi-length A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Picturesque Cutie Corset Lace-Up A-Line Midi Dress in Light Blue | Size: L | Woven Fabric
Show off your smooth moves in this strapless bodycon midi dress perfect for dressing up or down for any occasion! Fit & FeaturesRib knit fabric, sewn-in knit lining, moderate stretch, Strapless neckline, Side slit, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Smooth Talker Strapless Bodycon Midi Dress in Light Blue | Size: L | Knit Fabric
This sleeveless ribbed knit midi dress features a striking V-neckline and bodycon fit with a front slit detail for movement. Perfect for layering with a jacket and heels. Fit & FeaturesStretchy ribbed knit fabric, V-neckline, Spaghetti straps, Front slit, Midi-length bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Toasty Sweetheart V-Neck Bodycon Knit Midi Dress in Chartreuse | Size: L | Knit Fabric
The perfect chic sleeveless midi dress for grabbing dinner downtown! Crafted from smooth knit fabric, this crew neck dress boasts curve-accentuating ruched seams along the bodycon silhouette and a sleek midi-length hem. Pair with kitten heels and a clutch. Fit & FeaturesSmooth knit fabric, stretchy knit lining, Sleeveless crew neck, Side ruched seams, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Dinner Downtown Sleeveless Ruched Midi Dress in Brown | Size: M | Knit Fabric
On A Vacay Strapless Tropical Slit Maxi Dress
$19.97 $39.90
50% off
From sunny vacations to island getaways, this tropical maxi dress is destined to go with you on your next trip! Fit & FeaturesTropical palm print, mesh fabric lined with stretchy knit, Strapless neckline, Form-hugging silhouette, High side slit, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor On A Vacay Strapless Tropical Slit Maxi Dress | Size: XS | Mesh Fabric/Mesh Fabric
Windsor Blissful Cutie Halter Cutout Skater Dress in Yellow
$9.97 $46.90
79% off
Get swept off your feet in this cute skater dress for any casual occasion! With its halter neckline and cutout bodice, this dress is designed to show off your figure, while the ruffled mini-length hem adds a flirty touch. Fit & FeaturesGauze woven fabric, woven lining, Halter neckline with spaghetti strap ties, Stretchy smocked bust, Cutout bodice, Ruffled skater silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Blissful Cutie Halter Cutout Skater Dress in Yellow | Size: L | Gauze/Woven 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.