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.
$46.90
A brown woven midi dress with a ditsy floral pattern, corset bodice, and high front slit.
$44.90
An enchanting sage floral lace midi dress with ruffled trim, adjustable straps, and a flirty slit.
$20.97 $46.90 55% off
A black floral midi dress with a corset bodice, sweetheart neckline, and flirty front 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.
$59.90
A light blue woven midi dress featuring a corset bodice and lace-up back for a charming look.
$49.90
An ivory mesh midi dress with a dainty floral print, ruched seams, and a draped cowl neckline.
$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.
$59.90
A green satin off-the-shoulder midi dress with a sweetheart neckline and ruched wrap design.
$39.90
A captivating black floral mesh maxi dress with a lace-up back and flared hem.
$46.90
A strapless black satin midi dress featuring figure-flattering pleating and a high side slit.
$54.90
A royal blue glitter velvet midi dress with a V-neckline, padded bust, and pleated wrap bodice.
$36.90
A black knit midi dress with a sleeveless square neckline, ruching, and pleated mermaid silhouette.
$48.90
A pink ruffled mesh midi dress with a V-wired notch and flattering bodycon fit.
$54.90
An elegant white mesh midi dress featuring faux pearl embellishments, off-the-shoulder neckline, and bodycon fit.
$59.90
A chic navy blue midi dress with glitter knit fabric, sweetheart neckline, and lace-up back.
$44.90
A black midi dress with a floral flocked velvet pattern, halter neckline, and high side slit.
$49.90
A white cold shoulder midi dress featuring a bodycon silhouette with ruched seams and padded cups.
$19.97 $28.90 31% off
A breezy black midi dress featuring gauze fabric, a V-neck, adjustable straps, and hidden side pockets.
$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.
$59.90
A white satin wrap midi dress with a sleeveless cowl neckline and high-side slit.
$6.97 $39.90 83% off
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.
$36.90
A green sleeveless midi dress in stretchy knit with a square neckline and flared hem.
$42.90
A sleek green knit midi dress featuring a strapless sweetheart neckline, pleated overlay, and back slit.
$44.90
A light blue lace midi dress featuring a low-cut back, square neckline, and trumpet hem.
$38.90
A pink floral mesh midi dress featuring a strapless neckline and curve-hugging fit for elegant occasions.
$46.90
A sage green knit midi dress featuring a cowl halter neckline, pleated bust, and ruched bodycon silhouette.
$26.97 $59.90 55% off
A taupe floral chiffon midi dress featuring a halter neckline with a stone insert and flowy silhouette.
$52.90
A black knit midi dress featuring lace trim, flirty cutouts, and a high side slit.
$19.97 $59.90 67% off
A sage satin midi dress featuring a lace-trimmed bust, keyhole cutout, and high front slit.
$49.90
A pink knit midi dress featuring a pleated sweetheart neckline, cutout back, and form-hugging silhouette.
$17.97 $42.90 58% off
A chartreuse ribbed knit midi dress featuring a strapless sweetheart neckline, keyhole cutout, and high slit.
$36.90
A burgundy tube midi dress crafted from smooth, stretchy knit fabric with a flattering bodycon silhouette.
$44.90
An elegant burgundy velvet midi dress with a lace-trimmed sweetheart neckline and corset bodice.
$40.90
A strapless denim midi dress featuring a sweetheart neckline, side slit, and curve-hugging knit fabric.
$39.90
A brown tropical floral mesh midi dress featuring a strapless neckline, ruched sides, and a sheer flowy hem.
$59.90
A white satin midi dress featuring a strapless neckline, back bow detail, and flattering bodycon silhouette.
$39.90
A wine-colored knit bodycon midi dress featuring a sweetheart neckline, bust detail, and sleek silhouette.
$59.90
A navy blue satin midi dress with a V-neckline, strappy back, and side slit.
$9.97 $38.90 74% off
A sleek olive knit midi dress with off-the-shoulder sleeves and a high center slit.
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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
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: L | Lace Fabric/Knit Fabric
No one can deny your sultriness in this one-shoulder midi dress perfect for cocktail parties or receptions! The dress is crafted from a smooth double-lined knit fabric with plenty of stretch. It features a one-shoulder neckline, a figure-flaunting bodycon fit, and an asymmetrical midi-length hem. Fit & FeaturesSmooth double-lined knit fabric, moderate stretch, One-shoulder neckline, Bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Can't Deny It One-Shoulder Bodycon Midi Dress in Brown | Size: L | Knit Fabric
A girl like you can't help but show up in this midi dress and slay! The midi-length dress features a sultry off-the-shoulder sweetheart neckline, short-sleeve cuffs, a ruched and padded bust, a flattering side slit, and side ruched seams that accentuate your curves along the bodycon silhouette. Complete the look in strappy heels for a dinner party or wedding! Fit & FeaturesOff-the-shoulder sweetheart neckline, Short-sleeve cuffs, Ruched and padded bust, Side slit, ruched seams, Bodycon silhouette, midi-length hem, Mesh fabric, stretchy knit lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Can't Help It Mesh Off-The-Shoulder Midi Dress in Black | Size: S | Knit Fabric/Mesh Fabric
Step out looking like a dream in this sleeveless midi dress in a flattering bodycon fit perfect for dressing up. Fit & FeaturesStretchy knit fabric, knit lining, Square neckline, Spaghetti straps, Bodycon fit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Dreamy Energy Sleeveless Bodycon Midi Dress in Pink | Size: XS | Knit Fabric
Show off a chic and sleek look at a rooftop bar in this bodycon midi dress! Designed with a stretchy double-lined knit fabric, this curve-hugging dress will flaunt your stunning figure with its bodycon silhouette. The mid-length dress features a sleeveless square neckline for a flattering look, tank shoulder straps, a closed-back design, and a back slit for added allure. Style with strappy stiletto heels. Fit & FeaturesStretchy double-lined knit fabric, Square neckline, Tank shoulder straps, Closed back, Back slit, Bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Look Square Neck Bodycon Knit Midi Dress in Black | Size: XS | Knit Fabric
You'll be lookin' oh-so-fab in this ruched bodycon midi dress designed to hug your stunning curves. The cold-shoulder neckline adds a sweet touch to the alluring silhouette. Fit & FeaturesSheer mesh fabric with full-length knit lining, high stretch, Sweetheart neckline, bust seam outline, padded bra cups, Cold-shoulder design, thin tank shoulder straps, off-the-shoulder straps, Back zipper hook-eye closure, Ruching, Midi-length bodycon silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Looking Fab Cold-Shoulder Ruched Bodycon Midi Dress in Pink | Size: S | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
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: M | Knit Fabric
Create a dreamy vibe for your next garden party in this mesh midi dress featuring a dainty floral print pattern. The ruched seams will accentuate your curves along the bodycon silhouette. Fit & FeaturesSheer mesh fabric with full-length knit lining, high stretch, Floral print, padded bra cups, Sleeveless sweetheart neckline, lace bust insert, draped cowl neck overlay, Adjustable spaghetti straps, back zipper with hook-eye closure, Ruched side and back seams, Midi-length bodycon silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Garden Stroll Floral Mesh Midi Dress in Ivory | Size: S | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
The velvet dress features a sleeveless sweetheart neckline, a pleated bodice, and a midi-length hem. Complete the look with rhinestone earrings for the perfect wedding guest outfit. Fit & FeaturesVelvet fabrication, Sleeveless sweetheart neckline, Pleated bodice, Midi length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sophisticated Enchantment Velvet Midi Dress in Navy Blue | Size: S | Rhinestone/Velvet Fabric
Casual Midi Length Dresses
When it comes to building a wardrobe that’s as versatile as your social calendar, nothing hits the sweet spot quite like a casual midi dress. This is the piece you reach for when you want to look put together without trying too hard—whether you’re meeting your crew for a spontaneous brunch, running errands that somehow turn into a coffee date, or heading out for a low-key dinner that might just turn into an all-night adventure. The midi length is the ultimate power move: it’s flirty without being fussy, offering just the right amount of coverage while letting your favorite sneakers, boots, or strappy sandals steal a little of the spotlight. Think of it as your secret weapon for those days when you want to feel like the main character, even if you’re just making a Target run. And if you’re shopping for a friend (or, let’s be real, dropping hints for your next birthday), a casual midi dress is the kind of gift that says, “I know you, I see your vibe, and I get your need for comfort with a side of cute.”
Choosing a casual midi dress is all about embracing what makes you feel unstoppable. Maybe you’re all about soft knits that hug your curves and keep things cozy, or perhaps you gravitate toward breezy fabrics that move with you—perfect for those impromptu dance parties in your living room. Don’t sleep on those details, either: a little ruching here, a side slit there, or a playful tie at the waist can take your look from “just threw this on” to “runway ready” in two seconds flat. The beauty of the midi is in its adaptability; it’s the canvas for your personal style, ready to be layered with a denim jacket, dressed up with bold jewelry, or kept simple with your go-to crossbody bag. If you’re the kind of girl who likes to stand out, there’s a whole world of Unique Midi Dresses waiting to be discovered, with unexpected prints, textures, and silhouettes that are anything but basic.
Midi dresses aren’t just for the days when you want to keep it chill—they’re also the low-key heroes of your closet for those moments when plans pop up out of nowhere. They’re the answer to the “what do I wear?” panic before a family get-together, a casual office day, or a last-minute invite to a rooftop hang. And let’s not forget, they’re universally flattering, making them a go-to for gifting (because who doesn’t want a dress that just gets them?). Whether you’re dressing for your mood, your to-do list, or your next Insta pic, a casual midi dress is the piece that keeps you looking fresh, feeling fearless, and ready for whatever comes your way. So go ahead—find your new favorite, make it your own, and let your style do the talking.