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 bodycon fit and flared hem in stretchy knit.
$38.90
A black sleeveless ribbed knit midi dress with a V-neckline and chic high front slit.
$44.90
An enchanting sage floral lace midi dress with ruffled trim, adjustable straps, and a flirty slit.
$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.
$39.90
A brown knit midi dress with ruched detailing and an off-the-shoulder neckline for casual elegance.
$49.90
An ivory mesh midi dress with a dainty floral print, ruched seams, and a draped cowl neckline.
$42.90
A black ribbed knit midi dress featuring 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.
$54.90
A sage midi dress with faux pearl embellishments and an off-the-shoulder bodycon silhouette.
$36.90
A black knit midi dress with a sleeveless square neckline, ruching, and pleated mermaid silhouette.
$39.90
A curve-hugging ivory midi dress featuring ribbed knit fabric, a tie-back halter neckline, and open back.
$44.90
A black midi dress with a floral flocked velvet pattern, halter neckline, and high side slit.
$54.90
A black ribbed knit midi dress featuring a tie-dye pattern, scoop neckline, and back slit.
$29.97 $59.90 50% off
A white satin wrap midi dress with a sleeveless cowl neckline and high-side slit.
$36.90
A green sleeveless midi dress in stretchy knit fabric with a square neckline and flared hem.
$59.90
A chic navy blue midi dress with glitter knit fabric, sweetheart neckline, and lace-up back.
$49.90
A white cold shoulder midi dress featuring a bodycon silhouette with ruched seams and padded cups.
$109.90
A light blue satin midi dress featuring a sweetheart neckline, lace trim, and hidden side pockets.
$44.90
A chic black knit midi dress featuring an off-the-shoulder neckline, faux wrap front, and thigh-high slit.
$44.90
A grey ribbed knit midi dress with a sweetheart neckline and twist accent, perfect for casual outings.
$44.90
A light blue lace midi dress featuring a low-cut back, square neckline, and trumpet hem.
$59.90
A navy blue satin midi dress with a cowl neckline, high slit, and twist-back accent.
$46.90
A black knit midi sweater dress with an abstract striped pattern and a flattering bodycon silhouette.
$39.90
A burgundy knit midi dress featuring a one-shoulder neckline, bow trim, and flared hem.
$36.90
A sleek black knit midi dress with a halter neckline and flared mermaid silhouette.
$49.90
A pink knit midi dress featuring a pleated sweetheart neckline, cutout back, and form-hugging silhouette.
$34.90
A stunning emerald satin-knit midi dress with a strapless neckline and flattering ruched details.
$42.90
A sleek green knit midi dress featuring a strapless sweetheart neckline, pleated overlay, and back slit.
$29.97 $59.90 50% off
A navy blue satin midi dress with a V-neckline, strappy back, and side slit.
$52.90
A black knit midi dress featuring lace trim, flirty cutouts, and a high side slit.
$59.90
A white satin midi dress featuring a strapless neckline, back bow detail, and flattering bodycon silhouette.
$46.90
A sage green knit midi dress featuring a cowl halter neckline, pleated bust, and ruched bodycon silhouette.
$39.90
A wine-colored knit bodycon midi dress featuring a sweetheart neckline, bust detail, and sleek silhouette.
$45.90
A strapless bodycon midi dress in natural floral mesh with a back slit and no-slip grip lining.
$40.90
A strapless denim knit midi dress featuring a sweetheart neckline, side slit, and curve-hugging silhouette.
$42.90
A black knit midi dress featuring a front-tie bust, underbust cutout, and high front slit.
$54.90
An ivory satin midi dress with a corset seam bodice and pleated faux wrap hem.
$39.90
A sultry brown one-shoulder midi dress in smooth, double-lined knit fabric with a flattering bodycon fit.
$39.90
An olive ribbed knit bodycon midi dress with a halter V-neckline and center back slit.
$35.90
A pink sleeveless bodycon midi dress crafted from stretchy knit fabric with a square neckline.
$38.90
A sage green knit midi dress featuring a sleeveless square neckline, ruching, and a flared hanky hem.
$19.97 $33.90 41% off
A light blue strapless bodycon midi dress crafted from rib knit fabric with a side slit detail.
$64.90
An ivory satin midi dress featuring a pleated cowl neckline, underbust cutout, and high side slit.
$35.90
A white knit bodycon midi dress featuring a square neckline, spaghetti straps, and side ruched seams.
$46.90
A maroon satin strapless midi dress featuring a pleated neckline, form-hugging fit, and side slit.
$35.90
A black knit halter midi dress featuring a crisscross back, ruched sides, and a bodycon silhouette.
$46.90
A burgundy bodycon midi dress featuring floral lace texture, a square neckline, and a daring front slit.
Now Trending
Wrap yourself in a glam formal dress that captivates from the moment you enter the room! Margaret features a sleeveless cowl neckline, adjustable spaghetti straps, corset seams with flexible boning, and a ruched wrap midi silhouette. The dress is composed of a satin fabric that offers a form-hugging fit with minimal stretch. Complete look with heels and rhinestone earrings. Fit & FeaturesSleeveless cowl neckline, adjustable spaghetti straps, Built-in padded bust, Corset seams, flexible boning, Ruching, wrap midi skirt, Buttery soft silk fabric, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Margaret Formal Satin Wrap Midi Dress in Navy Blue | Size: M | Rhinestone/Satin Fabric
Radiate elegance in a formal dress that showcases your timeless style! Seona features a pleated cowl neckline, spaghetti straps, a cutout at the midriff, and a midi-length silhouette accented with a high side slit. The dress is composed of a silky-satin fabric that offers a form-hugging fit with a moderate stretch. Complete the look with rhinestone heels and a clutch. Fit & FeaturesSleeveless cowl neckline, pleating, Spaghetti straps, Cutout at the midriff, Midi-length silhouette, high side slit, Satin fabric, Form-hugging fit, moderate stretch, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Seona Formal Satin Midi Dress in Black | Size: XL | Rhinestone
Shine like a vision in the silky satin Samantha formal dress in a striking bodycon silhouette with a corset bodice that enhances your natural curves! Fit & FeaturesLined satin knit fabric, moderate stretch, Sleeveless square neckline, tank-style straps, Corset seam bodice, pleated side seam, Form-hugging silhouette, Faux wrap midi-length hem, Runs true to size, Where to Wear:Weddings, bridesmaids, cocktail parties, date nights, engagement parties, rehearsal dinner, graduations Free Shipping on All Orders Over $75. | Windsor Samantha Formal Satin Midi Dress in Green | Size: XS | Knit Fabric/Satin Fabric
Flirt up the room at your next dressy affair in this adorable skater dress designed with a floral jacquard satin fabric for a chic look. It features a sleeveless sweetheart neckline with ruching at the bust and a tie-front detail, a corset bodice with vertical seam detailing, a lace-up back design to create that snatched fit, a V-shaped drop waist, and a short skater skirt with an iconic fit-and-flare silhouette. Fit & FeaturesFloral jacquard satin fabric with lace-trim lining, Sweetheart neckline, ruched underwire bust, tie-front detail, Thin adjustable shoulder straps, lace-up back, Corset bodice with vertical seam detailing, flexible boning, V-shaped drop waist, Short skater skirt, fit-and-flare silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flirt It Up Floral Jacquard Satin Corset Skater Dress in Ivory | Size: M | Satin Fabric
Trend right and look timeless in the body-skimming Kristen formal satin midi dress at cocktail parties, graduations, and dressy birthdays! She features a sleeveless cowl neckline, spaghetti straps, a front ruched seam that accentuates your curves, a bodycon silhouette, and a sultry slit along her hem. The formal dress is composed of a luxurious silky satin-lined fabric with minimal stretch. Complete the look in rhinestone strappy heels. Fit & FeaturesSleeveless cowl neckline, spaghetti straps, Front ruched seam, slit accent, Bodycon silhouette, Midi-length hem, Lined silky satin fabric, minimal stretch, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Kristen Formal Satin Cowl Neck Midi Dress in Black | Size: L | Rhinestone/Satin Fabric
Wrap yourself up in this stylish satin mini dress for your next GNO! The dress features a sleeveless surplice V-neckline, spaghetti straps, a pleated side seam, a flattering bodycon silhouette, and a wrap hem. Complete the look in strappy block heels. Fit & FeaturesSleeveless surplice V-neckline, Spaghetti straps, Pleated side seam, Back zipper with hook-eye closure, Bodycon silhouette, wrap mini-length hem, Smooth satin fabric, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Wrapped Up In Style Satin Mini Dress in Green | Size: S | Satin Fabric
Windsor Harriet Formal Satin Corset Midi Dress in Red
$19.97 $49.90
60% off
Be radiant in the fiery Harriet formal satin midi dress perfect for bridesmaids, rehearsal dinners, or banquets! She features a figure-snatching corset-designed bodice with a square neckline, adjustable spaghetti straps, and flexible boning inserts. A side pleated seam leads to the bodycon silhouette showcasing a high front wrap slit along the midi-length hem. The formal dress is crafted from a glossy and sleek satin fabric that exudes sophistication! Complete the look with earrings and block heels. Fit & FeaturesSleeveless square neckline, adjustable spaghetti straps, Corset-designed bodice, flexible boning, Bodycon silhouette, high front wrap slit, midi-length hem, Satin knit fabric, moderate stretch, Pasties or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Harriet Formal Satin Corset Midi Dress in Red | Size: S | Knit Fabric/Satin Fabric
Chic and curve-hugging, the Lilith satin formal dress brings sleek confidence with its bodycon silhouette and sculptural details. A softly draped cowl neckline pairs with a striking cutout waist and wrap-front slit—because blending in was never the plan. Fit & FeaturesStretch satin fabric, sewn-in knit lining, Pleated cowl neckline, padded bra cups, Spaghetti straps, back zipper closure, Underbust cutout, Pleated faux wrap-front design, high side slit, Midi-length bodycon silhouette, Runs true to size, Where to Wear:School dances, weddings, bridal showers, engagement parties, rehearsal dinners, date nights, birthdays, dinner parties, galas, black tie events, milestone celebrations Free Shipping on All Orders Over $75. | Windsor Lilith Satin Cutout Wrap-Front Midi Dress in White | Size: XS | Knit Fabric/Satin Fabric
Get dressed to impress in this bodycon midi dress perfect for brides-to-be or a dressy date night! Fit & FeaturesSmooth knit fabric lined with stretchy knit, Square neckline, spaghetti straps, Side ruched seams, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Impressive Beauty Bodycon Midi Dress in White | Size: M | Knit Fabric
When timeless meets trendy—you get this sleek strapless satin midi. With a smooth curve-hugging fit and luxe shine, it’s your go-to for cocktail nights or any event that calls for instant glam. Fit & FeaturesCrepe and satin fabric lined with stretch knit, Strapless neckline, non-slip grip lining, Back zipper and hook-eye closure, Curve-hugging, midi-length silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Forever Icon Strapless Satin Midi Dress in Black | Size: XS | Satin Fabric