Casual Midi Length Dresses
Casual midi length dresses are your not-so-secret weapon for looking effortlessly put together, no matter what’s on your calendar. Whether you’re brunching with the squad, running errands, or just vibing through the day, these dresses have your back with that perfect blend of laid-back and totally cute. Slip into a midi and let your confidence do the talking—because every Windsor girl knows that comfy can still be seriously chic.
$42.90
A sleek pink knit midi dress featuring a cowl neckline, spaghetti straps, and a high front slit.
$38.90
A white sleeveless ribbed knit midi dress featuring a V-neckline and chic high front slit.
$44.90
An enchanting yellow floral lace midi dress featuring ruffled trim, ruched front, and a flirty front slit.
$49.90
A pink mesh and knit midi dress featuring cold-shoulder details, ruching, and a bodycon silhouette.
$39.90
A sage ribbed knit midi dress featuring a tie-back halter neckline, open back, and curve-hugging silhouette.
$64.90
A vintage-inspired ivory floral midi dress featuring a halter neckline, corset bodice, and lace-up back.
$36.90
A black knit midi dress with a sleeveless square neckline, ruching, and pleated mermaid silhouette.
$42.90
A black hacci rib knit midi dress featuring long sleeves, a sweetheart neckline, and a chic side slit.
$65.90
An ivory cotton midi dress featuring soft florals, a halter neckline, and a lace-up smocked back.
$42.90
A black polka dot halter midi dress with a plunging neckline and curve-hugging, mesh-lined fit.
$39.90
A bold red knit midi dress featuring a strapless sweetheart neckline, twist bust, and sultry cutouts.
$39.90
A yellow rib knit halter midi dress featuring a bodycon silhouette, open back, and side slit.
$39.90
A pink ribbed knit midi dress featuring a twisted sweetheart neckline and flattering bodycon silhouette.
$39.90
A green ribbed knit midi dress featuring a mock neckline and smooth, sculpting bodycon fit.
$50.90
A pink mesh bodycon midi dress featuring ruched detailing, sweetheart neckline, and adjustable spaghetti straps.
$14.97 $59.90 75% off
A green satin wrap midi dress with a sleeveless cowl neckline and high-side slit.
$49.90
An off-shoulder taupe midi dress featuring a floral print, ruched bodycon fit, and mesh-lined fabric.
$32 $45.90 30% off
A red brown knit midi dress featuring a halter cowl neckline, open back, and flattering slit accent.
$34.90
A strapless red midi dress in stretchy knit fabric featuring a fluid floral print and front slit.
$59.90
A navy blue satin midi dress with a cowl neckline, high slit, and twist-back accent.
$19.97 $39.90 50% off
A black ribbed knit midi dress featuring a strapless neckline, side ruching, and a bodycon silhouette.
$19.97 $42.90 53% off
A strapless mesh midi dress featuring a bold leopard and rose floral print with a ruched, bodycon fit.
$52.90
A mauve floral mesh midi dress featuring ruched detailing, off-the-shoulder neckline, and a form-hugging silhouette.
$59.90
A white floral eyelet midi dress featuring a ruffled A-line silhouette and whimsical tie-back design.
$44.90
A black crepe midi dress featuring a square neckline, tank straps, and an open tie-back cutout.
$42.90
A chic ivory ribbed knit midi dress featuring a mock neckline, keyhole detail, and bodycon silhouette.
$42.90
A vibrant orange mesh strapless midi dress featuring an abstract print and flattering bodycon silhouette.
$24.97 $54.90 55% off
A black velvet midi dress featuring a flocked floral pattern, cold-shoulder design, and ruched details.
$37 $52.90 30% off
A green floral strapless midi dress featuring ruffle trim, a high front slit, and airy woven fabric.
$36.90
A white rib knit midi dress featuring a sleeveless crew neckline and dramatic open back with tie detail.
$52.90
A strapless denim midi dress featuring a corset-inspired bodice, sweetheart neckline, and sleek bodycon silhouette.
$35.90
A strapless yellow floral eyelet knit midi dress with a bodycon fit and sleek silhouette.
$44.90
A floral ivory knit midi dress with a V-neckline, slim straps, and a chic front slit.
$42.90
A blue ribbed knit midi dress featuring a notched V-neckline, tank straps, and a bodycon silhouette.
$42.90
A black glitter-knit midi dress featuring a sweetheart neckline, spaghetti straps, and a sleek bodycon silhouette.
$44.90
A denim blue knit bodycon midi dress featuring a sweetheart neckline, pleated draping, and spaghetti straps.
$33 $46.90 30% off
A black mesh midi dress featuring a wired V-neckline, double tank straps, and allover flattering ruching.
$46.90
A sage green gingham midi dress featuring a strapless neckline, smocked back, and A-line silhouette.
$64.90
A white floral midi dress featuring a flowy A-line silhouette, high halter neckline, and open back.
$39.90
A banana yellow ribbed knit midi dress featuring a halter neckline, ruched bust, and keyhole cutout.
$39.90
A vibrant orange knit midi dress featuring a bodycon fit, scoop neckline, spaghetti straps, and side slit.
$9.97 $29.90 67% off
An olive green cable knit midi dress with a mock neck, form-hugging fit, and side slit.
$20.97 $46.90 55% off
A burgundy jacquard midi dress featuring a floral pattern, pleated square neckline, and bodycon silhouette.
$28.90
A form-hugging ivory midi dress in soft rib knit with a twist cutout back and side slit.
$9.97 $38.90 74% off
A sleek black knit bodycon midi dress featuring a halter sweetheart neckline and tie closure.
$19.97 $39.90 50% off
A striking red mesh midi dress featuring an abstract print, halter neckline, and figure-hugging silhouette.
$54.90
A gold satin midi dress featuring a fluid cowl neckline, adjustable straps, and a mermaid silhouette.
$39.90
A strapless white floral midi dress in textured knit eyelet fabric with a bodycon fit and back slit.
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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 White | Size: L | Knit Fabric
Sleek, soft, and made to flatter. This mock neck midi dress hugs in all the right places with side ruching and a soft modal blend knit fabric that gives casual polish. Perfect for weekday styling and weekend looks! Fit & FeaturesSoft modal-blend knit fabric, knit lining, moderate stretch, Sleeveless mock neck, Side ruched seams, Bodycon fit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Curve Flow Bodycon Midi Dress in Black | Size: XS | Knit Fabric
Flirty, fitted, and effortlessly classic. This halter midi dress features a plunging neckline and all-over polka dot print for that perfect mix of vintage charm and modern polish. Perfect for brunch, celebrations, or date night! Fit & FeaturesPolka dot print, mesh-lined fabric, moderate stretch, Halter V-neckline, Curve-hugging fit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Retro Romance Halter Midi Dress in Black | Size: S
Soft curves, no effort. This ribbed knit midi dress hugs just right with a bodycon fit that moves from dinner plans to late-night photos without missing a beat. Fit & FeaturesSoft rib knit fabric, sewn-in stretch lining, Sweetheart neckline with twisted bust detail, Spaghetti straps, Fitted bodice through the waist, Bodycon silhouette through the hips, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Soft Focus Moment Ribbed Knit Midi Dress in Pink | Size: M | Knit Fabric
Sun goddess maxi dress boasting a V-neckline with a unique metal accent and a body-skimming silhouette. Style with strappy sandals for a sunset dinner. Fit & FeaturesTextured knit fabric, soft knit stretchy lining, V-neckline with metal accent, Spaghetti straps, Body-skimming silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Into The Sun V-Neck Maxi Dress in Natural | Size: M | Knit Fabric
Moonlit Bloom Abstract Floral Maxi Dress in Brown
$35 $49.90
30% off
Slip into something sleek—this mesh maxi dress flaunts an abstract floral print that gives the illusion of an hourglass figure for an effortless allure at every event you're seen at! Fit & FeaturesAbstract floral print, mesh-lined stretch fabric, Scoop neckline, Spaghetti straps, Curve-hugging silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Moonlit Bloom Abstract Floral Maxi Dress in Brown | Size: L | Mesh Fabric
This midi is your secret weapon—clean, sculpting, and quietly commanding. The ribbed knit dress smooths and contours while the mock neck adds that cool, editorial structure that never tries too hard. Fit & FeaturesRib knit fabric, Mock neckline, Smooth bodycon fit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Effortless Impact Mock Neck Midi Dress in Green | Size: S | Knit Fabric
Soft florals, a cinched corset, and a skirt made to twirl—this one’s pure heart-eyes. The structured bodice keeps everything snatched while the skater silhouette brings effortless movement for brunch dates, parties, and photo-ready plans. Fit & FeaturesPoplin cotton fabric with a structured feel, floral print, tulle and woven linings, Square neckline with dainty ruffled trim, thin tank shoulder straps, Corset-inspired bodice with lace-up front detail, boning inserts, Back zipper closure, Drop waist silhouette, Flared skater silhouette, pleated detailing, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Picture Perfect Floral Corset Skater Dress in Pink | Size: L | Cotton
Show off pretty vibes in this adorable layered skater dress made with breezy eyelet knit fabric. Pair with sneakers for a cute casual look or wedges for a dressier style. Fit & FeaturesStretchy sheer eyelet knit fabric, partial knit lining, Square neckline, Spaghetti straps, Double-layered skater skirt, Short fit-and-flare silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Pretty Vibes Eyelet Knit Layered Skater Dress in White-2 | Size: L | Knit Fabric
That “did she just walk in?” kind of dress. The bodycon knit dress hugs in all the right places with a lace-up back that does the flirting for you. Fit & FeaturesTexture knit fabric, knit lining, High neckline, Spaghetti straps, Lace-up back, Bodycon fit, maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor It Girl High Neck Lace Up Maxi Dress in Mustard | Size: M | Knit Fabric