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 sage midi dress with a sleeveless cowl neckline, high slit, and stretchy knit fabric.
$36.90
An elegant sage off-the-shoulder midi dress with a flared hem and smooth knit fabric.
$38.90
A black sleeveless ribbed knit midi dress with a V-neckline and chic high front slit.
$44.90
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.
$39.90
A brown knit midi dress with ruched detailing and an off-the-shoulder neckline for casual elegance.
$38.90
A vibrant orange ribbed knit midi dress featuring a V-neckline, spaghetti straps, and a front slit.
$59.90
A light blue woven midi dress featuring a corset bodice and lace-up back for a charming look.
$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 featuring a turtleneck, long sleeves, and a high side slit.
$23.97 $52.90 55% off
A black floral mesh midi dress with a sweetheart neckline, ruching, and a flirty side slit.
$42.90
A navy blue velvet midi dress featuring a sleeveless sweetheart neckline and pleated bodice.
$38.90
A sage palm leaf print midi dress in stretchy knit fabric with a V-neckline and side slit.
$19.97 $38.90 49% off
A black knit midi dress with an off-the-shoulder halter V-neckline and bodycon fit.
$46.90
A pink floral midi dress featuring a corset bodice, lace-up back, and flirty front slit.
$46.90
A black floral midi dress with a corset bodice, sweetheart neckline, and flirty front slit.
$19.97 $42.90 53% off
A wine-colored glitter mesh midi dress with a V-neckline, ruching, and an asymmetrical hem.
$20.97 $46.90 55% off
A strapless sage satin midi dress with pleating and a form-hugging fit for elegant occasions.
$59.90
A green satin off-the-shoulder midi dress featuring a ruched faux wrap design and sweetheart neckline.
$54.90
A royal blue glitter velvet midi dress with a V-neckline, padded bust, and pleated wrap bodice.
$49.90
A black sheer midi dress with off-the-shoulder neckline, plunging v-neck, and high-side slit.
$20.97 $46.90 55% off
A sleek brown midi dress featuring leopard print satin and a sheer lace bust overlay.
$44.90
A grey ribbed knit midi dress with a sweetheart neckline and twist accent, perfect for casual outings.
$59.90
A glamorous red glitter lace midi dress with a corset bodice and high side slit.
$54.90
A black ribbed knit midi dress with a tie-dye pattern, scoop neckline, and back slit.
$35.90
A strapless ribbed knit midi dress in denim with asymmetric seams and a form-hugging silhouette.
$36.90
A black knit midi dress with a sleeveless square neckline, ruching, and pleated mermaid silhouette.
$54.90
An elegant white mesh midi dress featuring faux pearl embellishments, off-the-shoulder neckline, and bodycon fit.
$39.90
A chic black strapless midi dress with glitter mesh and a bodycon silhouette for elegant occasions.
$9.97 $38.90 74% off
A brown knit bodycon midi dress featuring flare cuff sleeves with tie accents and a V-neckline.
$49.90
A white cold shoulder midi dress featuring a bodycon silhouette with ruched seams and padded cups.
$32.90
A chic red sleeveless midi dress with ruched seams and a flattering bodycon silhouette.
$19.97 $29.90 33% off
A mauve knit midi dress with a square neckline and form-hugging fit for versatile styling.
$54.90
A sage midi dress with faux pearl embellishments and an off-the-shoulder bodycon silhouette.
$34.90
A stunning emerald satin-knit midi dress with a strapless neckline and flattering ruched details.
$34.90
A plum paisley mesh midi dress with a bodycon silhouette and flirty front slit.
$28 $39.90 30% off
A khaki woven midi dress featuring a smocked bodice, ruffled hem, and dual spaghetti straps.
$49.90
An ivory mesh midi dress with a dainty floral print, ruched seams, and a draped cowl neckline.
$34.90
A mocha knit strapless midi dress featuring side ruching, a bodycon silhouette, and a chic side slit.
$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.
$22.97 $49.90 54% off
An elegant black mesh midi dress with ruched sides, sheer sleeves, and a tiered ruffled hem.
$30.90
An ivory eyelet midi dress with a dainty floral print and strapless bodycon fit.
$19.97 $35.90 44% off
A strapless taupe midi dress with a tropical print and flared hem, perfect for vacations.
$36.90
A sleek black knit midi dress with a halter neckline and flared mermaid silhouette.
$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.
$19.97 $35.90 44% off
A strapless tropical midi dress in dark marsala with a bodycon silhouette and side 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 fitted, A-line silhouette, and a chic high front slit to showcase some leg. Style with embellished statement earrings for a cocktail party. Fit & FeaturesSleeveless cowl neckline, Spaghetti straps, High waist seam, Fitted A-line silhouette, High front slit, Knit fabric, plenty of stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek And Smooth High Slit Midi Dress in Navy Blue | Size: L | 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 Navy Blue | 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 Red | Size: XL | 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
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 Navy Blue | Size: S | 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: S | Woven Fabric
Nadine Formal Ruched Satin Midi Dress in Red
$9.97 $49.90
80% off
Make a stunning impression in this satin midi dress. Elevate your night out look in this luxe stretch satin midi cocktail dress with a flattering cowl neckline for a post-worthy look. Fit & FeaturesStretch satin fabric, minimal stretch, Cowl neckline, spaghetti straps, Form-hugging fit, Ruched high side slit, Midi-length hem, Runs true to size, Where to Wear:Weddings, cocktail parties, date night, Vegas, girl's night out, rooftop bars, celebrations Free Shipping on All Orders Over $75. | Windsor Nadine Formal Ruched Satin Midi Dress in Red | Size: S | Satin 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
Make a casual-chic impression in this long sleeve ruched midi dress showcasing a folded off-the-shoulder neckline and a bodycon silhouette. Pair with heels. Fit & FeaturesSmooth knit fabrication, moderate stretch , Off-the-shoulder neckline, foldover accent, Fitted long sleeves, Ruching, Midi length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Casual Affair Long Sleeve Ruched Midi Dress in Brown | Size: S | Knit 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: XL | Woven Fabric
Casual Midi Length Dresses
You know that thrill when you find a dress that just *gets* you? That’s the magic of a casual midi dress—she’s your go-to for every plan, every mood, every “let’s see where the day takes us” moment. Midi length is the ultimate sweet spot: flirty enough to show off those killer shoes, but chill enough to keep things effortless. Whether you’re hitting up brunch with your besties, running errands with a coffee in hand, or just vibing through your daily routine, a casual midi dress is the kind of ride-or-die piece that works overtime without breaking a sweat. The beauty is in the versatility: dress it up with layered jewelry and a bold lip for that surprise dinner invite, or keep it totally laid-back with sneakers and a denim jacket. Midi dresses are the definition of “throw on and go”—no overthinking, no drama, just instant cute. If you’re gifting, trust that a midi dress is the move for birthdays, graduations, or just because. It’s that one-size-fits-most vibe (with a little help from stretchy fabrics or adjustable ties), and the kind of gift that says, “I know your style, and I know you love looking amazing without trying too hard.”
Let’s talk details, because that’s where the love story really happens. When you’re picking out your next casual midi, think about what makes you feel unstoppable. Maybe it’s a soft ribbed knit that hugs you in all the right places, or a flowy silhouette that catches the breeze and turns every sidewalk into a runway. Pockets? Yes, please. Adjustable straps? We stan. Prints and colors? Go wild—florals, stripes, tie-dye, or classic solids, the world is your closet. If you’re all about comfort, look for stretchy waistbands and breathable fabrics that move with you (because who has time for stiff, scratchy dresses?). And don’t sleep on the power of a midi for travel—she packs easy, resists wrinkles, and always looks put-together, even after a day of adventures. For those group photos or spontaneous selfies, a midi dress is your secret weapon for looking cute with zero effort. No matter your vibe—girly, sporty, edgy, or glam—there’s a midi out there ready to be your new favorite. And if you’re craving even more inspo, check out our curated collection of Beautiful Midi Dresses for styles that’ll have you living your best life, one twirl at a time.