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 brown knit midi dress featuring a cowl neckline, spaghetti straps, and a chic high front slit.
$36.90
An elegant black off-the-shoulder midi dress with a stretchy knit fabric and flared hem.
$38.90
A black sleeveless ribbed knit midi dress with a V-neckline and chic high front slit.
$19.97 $44.90 56% off
A sage floral lace midi dress with a bodycon silhouette, ruffled hem, and adjustable straps.
$39.90
A black mesh off-the-shoulder midi dress featuring ruched details, padded bust, and a flattering side slit.
$49.90
An ivory mesh midi dress with a dainty floral print, ruched seams, and a draped cowl neckline.
$19.97 $32.90 39% off
A brown sleeveless midi dress in smooth knit fabric with side ruching and a flattering bodycon fit.
$33.90
A mocha strapless bodycon midi dress crafted from rib knit fabric with a side slit and moderate stretch.
$48.90
An elegant black off-the-shoulder midi dress with ruched sides and a flattering bodycon fit.
$42.90
A black ribbed knit midi dress with a turtleneck, long sleeves, and a high side slit.
$36.90
A black knit midi dress with a sleeveless square neckline, ruching, and pleated mermaid silhouette.
$42.90
A navy blue velvet midi dress featuring a sleeveless sweetheart neckline and pleated bodice.
$44.90
A romantic black mesh midi dress with a ruched bodycon silhouette and sheer floral overlay.
$42.90
A black knit midi dress featuring an off-shoulder neckline, cutout bodice, and front slit accents.
$56.90
An airy navy blue chiffon midi dress with a halter neckline, plunging front, and flowing A-line silhouette.
$45.90
A brown floral velvet mesh-lined midi dress featuring a bodycon fit, adjustable straps, and flared hem.
$39.90
A bold red knit midi dress featuring a strapless sweetheart neckline, twist bust, and sultry cutouts.
$45.90
A black midi dress featuring a ruched bodycon fit, cowl neckline, and adjustable spaghetti straps.
$46.90
A sultry black midi dress featuring flocked velvet roses, a cowl neckline, and a dramatic open back.
$19.97 $59.90 67% off
A white satin wrap midi dress with a sleeveless cowl neckline and high-side slit.
$38.90
A black knit midi dress with a plunging cowl neck, open back, and tie-back halter straps.
$24.97 $54.90 55% off
A soft pink satin midi dress featuring a cowl neckline and delicate strappy open back design.
$45.90
A red brown knit midi dress featuring a halter cowl neckline, open back, and flattering slit accent.
$42.90
A sleek black knit midi dress with side ruching, mock neck, and a flattering bodycon fit.
$52.90
A black burnout velvet floral midi dress featuring a sweetheart cowl neckline and ruffled front slit.
$39.90
An off-shoulder brown mesh midi dress with abstract swirls, twist detail, and a dramatic side slit.
$34.90
A strapless wine knit midi dress featuring side ruching, bodycon silhouette, and a chic side slit.
$44.90
A grey ribbed knit midi dress featuring a sweetheart neckline with a twist accent and long sleeves.
$19.97 $36.90 46% off
A sleek black knit midi dress featuring a cowl halter neckline, open back, and high side slit.
$23.97 $52.90 55% off
A pink floral mesh midi dress featuring a strapless sweetheart neckline and ruched bodycon silhouette.
$49.90
An off-shoulder taupe midi dress featuring a floral print, ruched bodycon fit, and mesh-lined fabric.
$49.90
A black mesh-lined stretch midi dress featuring a mock neck, open back, side slit, and bodycon fit.
$39.90
A brown knit tube midi dress featuring a form-hugging silhouette and a dramatic ruffled hem.
$34.90
A stunning emerald satin-knit midi dress with a strapless neckline and flattering ruched details.
$50.90
A mocha mesh bodycon midi dress featuring ruched detailing, sweetheart neckline, and adjustable spaghetti straps.
$59.90
A navy blue satin midi dress with a cowl neckline, high slit, and twist-back accent.
$19.97 $36.90 46% off
A sleek black knit midi dress with a halter neckline and flared mermaid silhouette.
$19.97 $36.90 46% off
A sultry brown knit midi dress featuring a plunge halter neckline, strappy open back, and side slit.
$44.90
A rose satin halter midi dress featuring a plunging neckline, open tie-back, and curve-hugging silhouette.
$42.90
A black halter midi dress with a plunging neckline and all-over polka dot mesh-lined fabric.
$44.90
A wine ribbed knit midi dress featuring an off-the-shoulder neckline, keyhole cutout, and front slit.
$39.90
A burgundy brushed knit midi dress with a square neckline and a curve-hugging bodycon fit.
$44.90
A sleeveless natural knit midi dress featuring a watercolor floral print, open back, and charming bow detail.
$44.90
A navy blue floral knit midi dress featuring a pleated waist, wrap-front slit, and bodycon silhouette.
$52.90
A green floral strapless midi dress featuring ruffle trim, a high front slit, and airy woven fabric.
$22.97 $49.90 54% off
A navy blue knit midi dress featuring a plunging halter neckline, open back, and bodycon silhouette.
$19.97 $42.90 53% off
A sleek green knit midi dress featuring a strapless sweetheart neckline, pleated overlay, and back slit.
$39.90
A burgundy knit midi dress featuring a one-shoulder neckline with bow trim and a flared hem.
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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
Windsor Chic Fall Vibe Ditsy Floral Corset Midi Dress in Brown
$20.97 $46.90
55% off
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: XS | Woven Fabric
Windsor Dinner Downtown Sleeveless Ruched Midi Dress in Brown
$19.97 $32.90
39% off
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: XS | 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 Mocha | Size: M | Knit 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
Windsor It Girl High Neck Lace Up Maxi Dress in Black
$19.97 $46.90
57% off
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 Black | Size: M | Knit Fabric
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: 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
This midi knows how to move—soft mesh, abstract swirls, and an off-shoulder twist that feels effortlessly seductive. The high side slit adds that perfect hint of drama, making every step a little more intentional. Fit & FeaturesAbstract printed mesh fabric, knit lining, Off-shoulder neckline with twist detail, Bodycon silhouette, High side slit for ease of movement, Runs true to size, Free Shipping on All Orders Over $75. | Windsor In Your Element Off-Shoulder Mesh Twist Midi Dress in Brown | Size: S | Knit Fabric/Mesh Fabric/Mesh Fabric
Strut looking casually sultry in this strapless midi dress that accentuates your curves and can easily be dressed up or down! Fit & FeaturesBrushed knit double-lined stretchy knit fabric, Strapless neckline, Side ruched seams, Bodycon silhouette, Midi-length hem, side slit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Casually Sultry Strapless Bodycon Midi Dress in Wine | Size: S | Knit Fabric