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 black knit midi dress with a cowl neckline, spaghetti straps, and a chic high slit.
$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
A sophisticated white midi dress featuring chiffon sleeves, a square neckline, and a ruched bodycon silhouette.
$39.90
A black mesh off-the-shoulder midi dress featuring ruched details, padded bust, and a flattering side slit.
$39.90
A brown knit midi dress with long sleeves, off-the-shoulder neckline, and ruched bodycon fit.
$46.90
A black floral midi dress with a corset bodice, sweetheart neckline, and flirty front slit.
$38.90
A vibrant orange ribbed knit midi dress featuring a V-neckline, spaghetti straps, and a front slit.
$48.90
An elegant black off-the-shoulder midi dress with ruched sides and a flattering bodycon fit.
$59.90
A light blue woven midi dress featuring a corset bodice and lace-up back for a charming look.
$42.90
A black ribbed knit midi dress featuring a turtleneck, long sleeves, and a high side slit.
$54.90
A sage midi dress with faux pearl embellishments and an off-the-shoulder bodycon silhouette.
$42.90
A navy blue velvet midi dress with a sleeveless sweetheart neckline and pleated bodice.
$49.90
An A-line midi dress in natural woven fabric with a smocked bodice, pleats, and hidden pockets.
$49.90
A black sheer midi dress with off-the-shoulder neckline, plunging v-neck, and high-side slit.
$46.90
A strapless black satin midi dress featuring pleating, a high side slit, and a form-hugging fit.
$32.90
A chic red sleeveless midi dress with ruched seams and a curve-hugging bodycon silhouette.
$36.90
A black knit midi dress with a sleeveless square neckline, ruching, and pleated mermaid silhouette.
$59.90
A green satin off-the-shoulder midi dress featuring a ruched faux wrap design and sweetheart neckline.
$39.90
A captivating black floral mesh maxi dress with a lace-up back and flared hem.
$44.90
A black midi dress with a floral flocked velvet pattern, halter neckline, and high side slit.
$54.90
A royal blue glitter velvet midi dress with a V-neckline, padded bust, and pleated wrap bodice.
$23.97 $52.90 55% off
An elegant black chiffon floral midi dress with a sweetheart neckline and adjustable straps.
$44.90
A grey ribbed knit midi dress with a sweetheart neckline and twist accent, perfect for casual outings.
$19.97 $30.90 35% off
An ivory eyelet midi dress with a dainty floral print and strapless bodycon fit.
$49.90
A white cold shoulder midi dress featuring a bodycon silhouette with ruched seams and padded cups.
$19.97 $39.90 50% off
A khaki woven midi dress with a smocked bodice, square neckline, and ruffled A-line silhouette.
$9.97 $38.90 74% off
A brown knit bodycon midi dress with flare cuff sleeves and a stylish V-neckline.
$39.90
A chic black strapless midi dress with glitter mesh and a bodycon silhouette for elegant occasions.
$34.90
A mocha knit strapless midi dress featuring side ruching, a bodycon silhouette, and a chic side slit.
$39.90
A red striped knit midi dress featuring a strapless neckline, cutout bodice, and bodycon silhouette.
$36.90
A sleek black knit midi dress with a halter neckline and flared mermaid silhouette.
$34.90
A stunning emerald satin-knit midi dress with a strapless neckline and flattering ruched details.
$44.90
A natural ribbed knit midi dress featuring a bold cutout bodice, side slit, and bodycon silhouette.
$44.90
An elegant black knit midi dress featuring an off-the-shoulder neckline, pleated wrap front, and thigh-high slit.
$9.97 $49.90 80% off
An elegant black mesh midi dress with ruched sides, sheer sleeves, and a tiered ruffled hem.
$22.97 $49.90 54% off
A light blue chiffon midi dress with floral print, puff sleeves, and a chic high front slit.
$39.90
A curve-hugging ivory midi dress featuring ribbed knit fabric, a tie-back halter neckline, and open back.
$59.90
A white satin wrap midi dress with a sleeveless cowl neckline and high-side slit.
$59.90
A chic navy blue midi dress with glitter knit fabric, sweetheart neckline, and lace-up back.
$59.90
A white floral eyelet midi dress featuring a ruffled A-line silhouette and whimsical tie-back design.
$36.90
A green sleeveless midi dress in stretchy knit fabric with a square neckline and flared hem.
$48.90
A sage mesh midi dress with a V-wired notch and tiered ruffled hem for elegant occasions.
$42.90
A black glitter knit midi dress with a cowl neckline, cross-back design, and high side slit.
$39.90
A burgundy knit midi dress featuring a one-shoulder neckline, bow trim, and flared hem.
$46.90
A black floral midi dress with a sweetheart halter neckline and flowy A-line silhouette.
$44.90
An elegant burgundy velvet midi dress with a lace-trimmed sweetheart neckline and corset bodice.
$36.90
A burgundy tube midi dress crafted from smooth, stretchy knit fabric with a flattering bodycon silhouette.
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Simple and sleek, this smooth knit midi dress is a perfect choice. It features a sleeveless cowl neckline, spaghetti straps, a high waist seam, a form-hugging silhouette, and a chic high front slit to showcase some leg. Fit & FeaturesSleek knit fabric, stretchy knit lining, Cowl neckline, Spaghetti straps, High waist seam, Form-hugging silhouette, High front slit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek And Smooth High Slit Midi Dress in Navy Blue | Size: M | Knit Fabric
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 Black | Size: S | 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 Green | Size: S | Rhinestone
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
Sophistication meets sultry on the Marjorie formal dress perfect for cocktail parties and dressy family get-togethers. She features sheer chiffon peasant long sleeves, a square neckline, a bodycon silhouette, and a front ruched seam leading to the skin-flaunting slit along her midi-length hem. The formal dress is composed of a lined crepe fabric with a moderate stretch. Style with a chic clutch and heels to complete the look! Fit & FeaturesSheer chiffon peasant long sleeves, square neckline, Front ruched seam, slit detail, Bodycon silhouette, Midi-length hem, Lined crepe fabric, moderate stretch, Bra-friendly design, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Marjorie Formal Chiffon Sleeve Midi Dress in White | Size: XL | Chiffon/Crepe Fabric
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
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
Look enchanting in this floral ruffled lace midi dress showcasing a bodycon silhouette and flirty slit for movement. Pair with heels. Fit & FeaturesSheer floral lace fabric with knit lining, moderate stretch, Square neckline, Adjustable spaghetti straps, Ruched front, Asymmetric midi-length hem with ruffled trim, front slit, Bodycon silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Enchanted Moment Floral Ruffled Lace Midi Dress in Sage | Size: XL | Lace Fabric/Knit Fabric
Set the tone for spring dressing in this halter floral midi dress. The voluminous fit and flare silhouette embodies vintage charm with pretty modern details like a corset bodice and lace-up back design. Fit & FeaturesDelicate floral print, Poplin woven fabric, tulle and woven linings, Halter V-neckline with tie straps, wired underbust, Side zipper and hook-eye closure, Corset bodice, flexible boning, lace-up back, Fit and flare silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Set For Spring Halter Corset Floral Midi Dress in Natural | Size: XS | Woven Fabric
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: L | Woven Fabric
Casual Midi Length Dresses
When it comes to building your dream wardrobe, nothing hits that sweet spot between comfort and confidence quite like a casual midi dress. This is the piece you reach for when you want to look effortlessly put-together without trying too hard—think throw-on-and-go energy, but with a major style payoff. Midi length is that magic middle ground: long enough to keep things chic and breezy, but short enough to show off a killer pair of kicks or that ankle bracelet you picked up on a whim. Whether you’re running errands, heading to brunch with your girls, or just need something that’ll take you from coffee runs to late-night hangs, the casual midi dress is your ride-or-die. It’s the go-to for those days when you want to be comfy but still turn heads, the piece you can dress up with a belt and some chunky jewelry or keep low-key with sneakers and a messy bun. If you’re the queen of last-minute plans (or gifting to one), a midi dress is the ultimate “I’ve got you” present—versatile, easy to fit, and basically guaranteed to become a closet MVP.
What makes the casual midi dress such an icon isn’t just the way it looks—it’s how it makes you feel. Picture this: you’re running out the door, iced coffee in hand, and you toss on a midi that moves with you, never against you. The fabric skims your curves just right, the hem hits at that oh-so-flattering spot, and suddenly you’re strutting like the sidewalk is your personal runway. That’s the power of a midi. It’s the dress that says you’re here to have fun, but you’re not here to mess around. Shopping for one? Think about what makes you feel like your best self. Maybe it’s a soft ribbed knit that hugs your body, or a flowy woven style that twirls when you do. Look for thoughtful details—adjustable straps, pockets (yes, please!), or a side slit for a little extra sass. And don’t sleep on color and print: go bold if you’re feeling fearless, or keep it classic with neutrals that play nice with everything in your closet. Midi dresses are also a total crowd-pleaser for gifts—ideal for birthdays, graduations, or just because your bestie deserves a “you’re the main character” moment.
Ready to find your new favorite? The best part about midi dresses is how they fit into literally any vibe you’ve got going. Style it with a denim jacket and sneakers for a laidback look that still feels intentional, or add a statement belt and heeled sandals when you want to dial up the drama. Take it to the office with a blazer, or wear it solo for a day at the park—no matter where you’re headed, a midi has your back. And if you want to see even more ways to rock this iconic silhouette, check out our curated collection of Beautiful Midi Dresses for endless inspo. Whether you’re shopping for yourself or looking for the perfect gift, a casual midi dress is always a good idea—because life’s too short not to dress like the main character.