Flowy Summer Midi Dresses
Flowy summer midi dresses are your ticket to effortless style and main character energy. Whether you’re twirling through brunch plans or making an entrance at that rooftop soirée, these dreamy picks are all about movement, confidence, and a touch of flirt. Get ready to serve looks that turn heads and keep the good vibes going—because every day deserves a little drama (the fun kind, obviously).
$59.90
An ivory cotton floral midi dress featuring puff sleeves, a V-neckline, and a flattering A-line silhouette.
$30 $42.90 30% off
A natural woven fabric midi dress featuring a halter neckline, open back, and beaded tie waist.
$20.97 $46.90 55% off
An ivory woven A-line midi dress featuring lace-up details, smocked bust, and hidden side pockets.
$34.90
A plum floral knit midi dress featuring a strapless neckline and stylish front slit.
$42.90
A sleek sage midi dress with a cowl neckline, spaghetti straps, and a chic high front slit.
$44.90
An enchanting sage floral lace midi dress with ruffled trim, adjustable straps, and a flirty slit.
$46.90
A black floral midi dress with a corset bodice, sweetheart neckline, and flirty front slit.
$59.90
A light blue woven midi dress featuring a corset bodice and charming lace-up back detail.
$64.90
A natural cotton midi dress featuring a watercolor floral print, corset bodice, and voluminous A-line silhouette.
$49.90
An A-line midi dress in natural woven fabric featuring a smocked bodice, pleats, and hidden pockets.
$46.90
An ivory striped knit midi dress with cutouts, adjustable straps, and dual side slits.
$39.90
A curve-flaunting black floral mesh maxi dress with a lace-up strappy back and flared hem.
$59.90
A navy blue satin midi dress with a high slit and elegant cowl neckline.
$23.97 $52.90 55% off
An elegant black chiffon floral midi dress with a sweetheart neckline and adjustable straps.
$59.90
An effortlessly pretty chiffon midi dress with a floral print, ruffled tiers, and smocked details.
$19.97 $39.90 50% off
A khaki woven midi dress with a smocked bodice, square neckline, and ruffled A-line silhouette.
$42.90
A light blue woven midi dress featuring dainty florals, adjustable straps, and a front slit.
$59.90
A white floral eyelet midi dress featuring a ruffled A-line silhouette and whimsical tie-back design.
$22.97 $49.90 54% off
A light blue chiffon midi dress with puff sleeves, floral print, and a chic high front slit.
$59.90
A green satin wrap midi dress featuring a sleeveless cowl neckline and high-side slit.
$36.90
A green sleeveless midi dress in stretchy knit with a square neckline and flared hem.
$46.90
A black floral midi dress with a sweetheart halter neckline and flowy A-line silhouette.
$69.90
A strapless natural gauze midi dress featuring a smocked bodice and cascading ruffled silhouette.
$38.90
A pink floral mesh midi dress featuring a strapless neckline and curve-hugging, lined silhouette.
$52.90
A white floral A-line midi dress featuring puff short sleeves, a square neckline, and a flirty front slit.
$46.90
A romantic natural floral mesh midi dress featuring a halter V-neck, open back, and ruffled trim.
$59.90
A taupe floral chiffon midi dress featuring a halter neckline with a stone insert and flowy silhouette.
$49.90
A strapless black woven midi dress featuring a color block bodice, flowy hem, and hidden pockets.
$39.90
A brown tropical floral mesh midi dress featuring a strapless neckline, ruched sides, and a sheer flowy hem.
$52.90
An ivory woven A-line midi dress featuring a sweetheart neckline, underbust cutout, and adjustable straps.
$28.90
A black gauze midi dress featuring a flowy silhouette, V-neckline, adjustable straps, and hidden side pockets.
$35.90
A strapless white floral midi dress with a form-hugging fit and chic flared hem.
$44.90
A flowy green gauze midi dress featuring a strapless smocked bodice and tiered A-line silhouette.
$44.90
A natural striped knit midi dress featuring a halter neckline, cutout bodice, and lace-up open back.
$52.90
A beige cotton midi dress featuring a smocked geometric bodice, pleated A-line silhouette, and side pockets.
$59.90
A glamorous black satin wrap midi dress with a cowl neckline and adjustable spaghetti straps.
$59.90
A green satin midi dress with a pleated cowl neckline, midriff cutout, and high side slit.
$38.90
A white sleeveless ribbed knit midi dress featuring 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.
$54.90
A wine-colored satin midi dress with a corset seam bodice and pleated faux wrap hem.
$9.97 $49.90 80% off
A red satin midi dress with a cowl neckline and side ruching for an elegant silhouette.
$59.90
A dreamy white floral maxi dress with an open tie back and ruffled silhouette.
$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 figure-flattering pleating and a high side slit.
$32.90
A breezy white eyelet knit skater dress featuring a square neckline and double-layered flared skirt.
$36.90
A mauve knit midi dress with a sleeveless square neckline and pleated mermaid silhouette.
$42.90
A rust floral skater dress in airy rayon with tie-back halter straps and an open back.
$42.90
An elegant blue floral midi dress with a strappy back, cowl neckline, and mesh fabric.
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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
Flowy Summer Midi Dresses
When the days get longer and the sun practically begs you to stay out past curfew, flowy summer midi dresses become the ride-or-die wardrobe staple you never knew you needed—until now. These dresses are made for the girls who want to look like they just stepped out of a music video, whether they’re heading to a rooftop brunch, a spontaneous road trip, or a backyard bash that turns into an all-nighter. With their twirl-worthy silhouettes, these midis are the ultimate confidence boosters, letting you move through every moment with that effortless, main character energy. The beauty of a midi? It’s just the right amount of drama—long enough to make you feel a little mysterious, but short enough to keep things fun and flirty. And let’s be honest: nothing says “I’m here to make memories” quite like a dress that catches the breeze and turns every sidewalk into your personal runway.
Choosing the perfect flowy summer midi dress is all about embracing your vibe and letting your personality shine. Some Windsor girls go for soft, romantic florals that look like they belong in a field of wildflowers (or at least on your Insta feed), while others turn up the heat with bold colors and playful prints that demand a double-take. Fabric matters, too—think lightweight, breathable materials that keep you cool when the temperature goes up and you’re dancing under the stars. Adjustable straps, smocked bodices, and tiered skirts are your best friends for that custom-fit feel, and pockets? Don’t even get us started—total game changer. These dresses are the ultimate plus-one for everything from birthday dinners to last-minute getaways, and they make the sweetest gifts for your besties, sisters, or anyone who deserves a little extra sparkle in their closet. Styling is a breeze—just add your favorite sandals, a stack of bracelets, and a killer attitude, and you’re ready for whatever adventure comes your way.
Whether you’re curating your own collection of flowy summer dresses midi or searching for that one show-stopping look, there’s no wrong way to rock a midi. If you’re feeling extra, layer on a denim jacket or a lightweight cardigan for those breezy nights, or keep it simple and let your dress do all the talking. And if you’re craving something a little more elevated, don’t miss our curated picks of Elegant Summer Midi Dresses—perfect for those moments when you want to dial up the drama and leave a lasting impression. No matter how you style it, a flowy midi is your ticket to feeling fearless, fabulous, and totally unstoppable, all season long.