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.
$36.90
An elegant black off-the-shoulder midi dress with a stretchy knit fabric and flared hem.
$38.90
A white sleeveless ribbed knit midi dress featuring a V-neckline and chic high front slit.
$19.97 $33.90 41% off
A mocha strapless bodycon midi dress crafted from rib knit fabric with a side slit and moderate stretch.
$39.90
A black mesh off-the-shoulder midi dress featuring ruched details, padded bust, and a flattering side slit.
$48.90
An elegant black off-the-shoulder midi dress with ruched sides and a flattering bodycon fit.
$36.90
A black knit midi dress with a sleeveless square neckline, ruching, and pleated mermaid silhouette.
$42.90
A black ribbed knit midi dress with a turtleneck, long sleeves, and a high side slit.
$42.90
A navy blue velvet midi dress with a sleeveless sweetheart neckline and pleated bodice.
$44.90
A romantic black mesh midi dress with a ruched bodycon silhouette and sheer floral overlay.
$45.90
A romantic brown floral velvet mesh midi dress with a bodycon fit, adjustable straps, and flared hem.
$42.90
A sleek black knit midi dress with side ruching, mock neck, and a flattering bodycon fit.
$39.90
A bold red knit midi dress featuring a strapless sweetheart neckline, twist bust, and sultry cutouts.
$19.97 $59.90 67% off
A white satin wrap midi dress with a sleeveless cowl neckline and high-side slit.
$44.90
A rose satin halter midi dress featuring a plunging neckline, open tie-back, and curve-hugging silhouette.
$19.97 $34.90 43% off
A stunning emerald satin-knit midi dress with a strapless neckline and flattering ruched details.
$32 $45.90 30% off
A red brown knit midi dress featuring a halter cowl neckline, open back, and flattering slit accent.
$44.90
A grey ribbed knit midi dress with a sweetheart neckline and twist accent, perfect for casual outings.
$49.90
An off-shoulder taupe midi dress featuring a floral print, ruched bodycon fit, and mesh-lined fabric.
$59.90
A navy blue satin midi dress with a cowl neckline, high slit, and twist-back accent.
$42.90
A strapless burgundy midi dress in stretchy knit fabric with ruching and a ruffled side slit.
$44.90
A wine ribbed knit midi dress featuring an off-the-shoulder neckline, keyhole cutout, and front slit.
$42.90
A black halter midi dress with a plunging neckline and all-over polka dot mesh-lined fabric.
$39.90
A burgundy knit midi dress featuring a one-shoulder neckline, bow trim, and flared hem.
$37 $52.90 30% off
A green floral strapless midi dress featuring ruffle trim, a high front slit, and airy woven fabric.
$27 $38.90 31% off
A black strapless midi dress in stretch knit with a twist-front bodice and underbust cutout.
$19.97 $39.90 50% off
A blue mesh midi dress featuring a cowl neckline, curve-hugging fit, and bold floral print.
$52.90
A moody raisin knit midi dress featuring a plunge halter neckline, ruched fit, and front sash detail.
$37 $52.90 30% off
A black knit midi dress featuring lace trim, flirty cutouts, and a high side slit.
$52.90
An ivory floral knit midi dress featuring a pleated halter neckline and strappy lace-up back detail.
$20.97 $45.90 54% off
A dark marsala floral mesh midi dress featuring a curve-hugging silhouette and sultry open back.
$29.90
An olive green cable knit midi dress with a mock neck, form-hugging fit, and side slit.
$27 $38.90 31% off
A sleek black knit bodycon midi dress featuring a halter sweetheart neckline and tie closure.
$42.90
A chic ivory ribbed knit midi dress featuring a mock neckline, keyhole detail, and bodycon silhouette.
$52.90
A sultry plum halter midi dress with floral satin soutache, open back, and a side slit.
$39.90
A green ribbed knit midi dress featuring a mock neckline and smooth, sculpting bodycon fit.
$54.90
A gold satin midi dress featuring a fluid cowl neckline, adjustable straps, and a mermaid silhouette.
$42.90
A wine mesh midi dress featuring a ruched bodycon silhouette, cowl neckline, and adjustable straps.
$44.90
A black rib knit midi dress featuring an off-shoulder foldover neckline with gold hardware accent.
$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 green floral knit midi dress featuring an off-shoulder neckline, ruched body, and front slit.
$42.90
A brown satin midi dress featuring a cowl neckline, adjustable straps, and a curve-hugging silhouette.
$19.97 $54.90 64% off
A white satin midi dress featuring a deep cowl neckline, halter straps, open back, and side slit.
$44.90
A sage knit midi dress featuring a draped neckline, lace-up back, ruching, and a front slit.
$46.90
A burgundy jacquard midi dress featuring a floral pattern, pleated square neckline, and bodycon silhouette.
$44.90
A black ribbed knit midi dress featuring an off-shoulder foldover neckline and a chic side slit.
$27 $38.90 31% off
A sultry red midi dress featuring metallic chain straps, a cowl neckline, and a curve-hugging knit fabric.
$39.90
A striking red mesh midi dress featuring an abstract print, halter neckline, and figure-hugging silhouette.
$42.90
A strapless mesh midi dress featuring a bold leopard and rose floral print with a ruched, bodycon fit.
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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
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 Brown | Size: XS | 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
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: M | Mesh Fabric
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
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: L | Knit Fabric
Giving flirty fairytale but make it chic. This lace-trimmed maxi dress hugs like a dream and serves up soft-girl glam with a sultry high side slit. Perfect for garden parties, shower celebrations, and dressy dates. Fit & FeaturesFloral print, mesh-lined fabric, Lace sweetheart neckline and shoulder straps, Back zipper closure, High side slit, Form-hugging silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Garden Party Chic Lace Floral Maxi Dress in Natural | Size: XS
Chic Paradise Halter Open Back Slit Midi Dress in Red Brown
$32 $45.90
30% off
Own the spotlight on vacation in this midi dress! Featuring a bold halter neckline and an sexy open back, this dress exudes allure, while the bodycon silhouette and slit add a flattering look. Fit & FeaturesSlinky knit fabric, smooth stretchy knit lining, Halter cowl neckline, beaded spaghetti strap tie, Open back with spaghetti strap tie, Bodycon silhouette, Slit accent, midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Paradise Halter Open Back Slit Midi Dress in Red Brown | Size: M | 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
This curve-hugging maxi brings the heat with sultry lace, sheer mesh, and sky-high slits—made for nights when playing it safe isn't on the mood board! Fit & FeaturesLeopard print, mesh fabric, stretchy knit lining, Lace sweetheart neckline, lace bust, lace shoulder straps, High side slits, Form-hugging fit, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Born to Be Bold Lace Leopard Maxi Dress in Brown | Size: M | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric