Summer Drop Waist Dresses
When it comes to making an entrance, nothing says main character energy quite like summer drop waist dresses. These flirty, flowy fits are your secret weapon for turning sidewalks into runways and brunches into photo ops. Effortlessly cool and made for every spontaneous adventure, summer drop waist dresses are here to give you that carefree confidence—so go ahead, twirl a little longer and let the compliments roll in.
$64.90
A white woven skater dress featuring a lace-up back, ruched bust, and tiered A-line silhouette.
$39.90
A light blue lace mini dress featuring beaded spaghetti straps, sweetheart neckline, and pleated A-line silhouette.
$39.90
A pink strapless skater dress with a glitter knit fabric and tiered ruffled hem.
$42.90
A sleeveless black midi dress featuring a crew neck, drop waist, and mixed knit-poplin fabrics.
$39.90
A navy blue strapless mini dress featuring a tiered A-line silhouette and stretchy knit fabric.
$54.90
An ivory satin skater dress with a halter neckline, drop waist, and bubble hem for semi-formal events.
$29.90
A flirty white skater dress featuring a strapless neckline and tiered eyelet knit design.
$52.90
A pink skater dress with puff sleeves, lace trim, and a playful bubble hem.
$49.90
A playful denim halter skater dress featuring a bust cutout, drop waist, and pleated short silhouette.
$49.90
A white cotton gauze mini dress featuring cherry embroidery, a plunge halter neckline, and a skater silhouette.
$59.90
A black sequin skater dress with an open back and tie-back bow, perfect for parties.
$39.90
An ivory lace skater dress with an off-the-shoulder neckline and sheer long fitted sleeves.
$19.97 $44.90 56% off
A strapless black knit mini dress featuring a drop waist and tiered ruffled asymmetric hem for flirty style.
$59.90
A black eyelet woven skater dress featuring a strapless smocked bodice and tiered ruffled mini skirt.
$42.90
A red gingham skater dress with lace trim and button details for a charming spring look.
$59.90
A chic satin skater dress in yellow featuring a lace-up corset bodice and lace trim neckline.
$20.97 $46.90 55% off
An ivory woven A-line midi dress featuring lace-up details, smocked bust, and hidden side pockets.
$69.90
An ivory skater dress with floral appliques, open back, and plunge V-neckline for whimsical elegance.
$59.90
A pink woven mini dress featuring a tie-front design, pleated hem, and spaghetti strap ties.
$46.90
An adorably chic taupe skater dress featuring a plaid print and strapless sweetheart neckline.
$52.90
A strapless black mini dress featuring sheer lace, a drop waist, and tiered ruffled A-line silhouette.
$49.90
An enchanting sage skater dress featuring sheer lace, a twist-front bust, and adjustable spaghetti straps.
$48.90
A flirty white mini skater dress featuring a breezy eyelet knit and charming tie-back detail.
$49.90
An A-line midi dress in natural woven fabric with a smocked bodice, pleats, and hidden pockets.
$64.90
A luxe black velvet skater dress with an off-the-shoulder neckline and pleated drop-waist design.
$46.90
An adorable white eyelet mini dress with a flirty tie-back and ruffled A-line silhouette.
$44.90
A flowy green gauze midi dress featuring a strapless smocked bodice and tiered A-line silhouette.
$42.90
A rust floral skater dress in breezy rayon with tie-back halter straps and an open back.
$34.90
An off-white sheer lace mini skort featuring a drop waist and tiered ruffled overlay with hidden shorts.
$59.90
An ivory A-line maxi dress with gauze fabric, sheer lace insets, and a faux leather belt.
$46.90
A charming floral babydoll mini dress in natural with a flowy ruffled silhouette and smocked bust.
$49.90
An olive green gauze skater dress featuring a tie-front, ruffled tiers, and adjustable spaghetti straps.
$65.90
A strapless floral skater dress featuring a bustier bodice, sweetheart neckline, and hidden side pockets.
$42.90
A navy blue paisley skater dress with a halter V-neckline and playful tie-back design.
$38.90
A white striped mini dress featuring a strapless neckline, flirty cutout, and stretchy rib knit fabric.
$49.90
An ivory floral skater dress featuring a corset bodice, lace-up back, and tie shoulder straps.
$44.90
An ivory satin skater dress featuring a square neckline, ruched bust, and adjustable shoulder straps.
$14.97 $59.90 75% off
A chic black taffeta skater dress with a strapless sweetheart neckline and drop waist seam.
$69.90
A yellow satin skater dress featuring a lace-up back, corset bodice, and bow tie shoulder straps.
$34.90
A flirty pink floral mini dress with a strappy open back and A-line silhouette.
$36.90
A red eyelet knit romper featuring a strapless neckline, drop waist, and tiered ruffled overlay.
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Have a twirl-worthy moment in this gorgeous and glam satin skater dress. It features a sleeveless square neckline, adjustable spaghetti straps that lead to a cross-back and lace-up back design, a fitted bodice with a high waist, and a flirty skater silhouette. Style this dress with rhinestone earrings and new heels. Fit & FeaturesSleeveless, square neck, adjustable spaghetti straps, Built-in padded bust, Lace-up back design, Fitted bodice, high waist seam, Skater pleated silhouette, Satin fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor A Moment In Satin Skater Dress in Blue | Size: L | Rhinestone/Satin Fabric
Lustrous silk for your fancy needs. Show up to the celebration in this satin skater dress designed to fit and flatter every figure in a sleeveless cowl neckline, spaghetti straps, and a form-fitting bodice that leads to a short-length hem. Complete the look in fab block heels. Fit & FeaturesSleeveless cowl neckline, spaghetti straps, Form-fitting bodice, Skater style skirt, Short-length hem, Silky smooth satin fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Silky Chic Satin Skater Dress in Blue | Size: L | Satin Fabric
A chic staple skater dress featuring a flirty off-the-shoulder folded neckline and a short-length perfect for styling with boots or heels. Fit & FeaturesRibbed knit fabric with plenty of stretch, Off-the-shoulder neckline, fold-over accent, Long fitted sleeves, Short-length hem, Skater silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Staple Ribbed Knit Skater Dress in Pink | Size: S | Knit 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 Black | Size: S | Satin Fabric
Bling Fling Satin Rhinestone Skater Dress in Royal Blue
$9.97 $45.90
78% off
Show off a hint of bling in this satin skater dress for your next dressy soiree! Adorned with detachable rhinestone-embellished straps for a stunning sparkle, this dress will be the night's hit. The smooth satin-knit fabric offers plenty of stretch for comfortable wear. The short dress features a sleeveless square neckline, ruched side seams at the bodice, and a flattering fit-and-flare skater silhouette. Complete your look with rhinestone bow heels. Fit & FeaturesStretchy smooth satin-knit fabric, knit lining at the bust, Sleeveless square neckline, Detachable rhinestone-embellished thin straps, Side ruched seams at the bodice, High waist seam, Fit-and-flare skater silhouette, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Bling Fling Satin Rhinestone Skater Dress in Royal Blue | Size: XS | Knit Fabric/Rhinestone/Satin Fabric
Create a sweet summer look that is oh-so-darling with this drop-waist skater dress. Designed with a lightweight woven fabric, the bodice is accented with a dainty lace trim for a pretty vibe. The short dress features a sleeveless sweetheart neckline, a ruched bust with a small tie-front adjustable detail, and thin tank straps leading to an alluring lace-up back for a customized fit. The asymmetric drop-waist is detailed with pleated side panels, flowing down to a tiered A-line silhouette for a flirtatious look. Style with hoop earrings and a charm necklace. Fit & FeaturesWoven fabric with lace trim woven lining, Sweetheart neckline, ruched bust, adjustable tie-front, Tank straps, lace-up back design, Back zipper and hook-eye closure, Asymmetric drop-waist, pleated side panels, Tiered A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Darling Woven Drop-Waist Skater Dress in White | Size: XS | Woven Fabric
Short and sweet, this adorable floral skater dress will perfect your spring vibe. The lace-up corset bodice and V-shaped drop waist snatches your waist, while the flared A-line silhouette gives that flirty flair. Fit & FeaturesSmooth woven fabric with woven lining, sheer lace trims, no stretch, Sleeveless sweetheart neckline, underwire, ruched bust, tie-front detail, Thin adjustable shoulder straps, Corset bodice, structured boning, pleating, lace-up back, hidden zipper with hook-eye closure, V-shaped drop waist, Short skater silhouette, floral print, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Babe Corset Drop Waist Floral Skater Dress in Ivory | Size: XL | Sheer Lace Fabric/Woven Fabric
Capture hearts with your sweet look in this airy eyelet knit skater dress. You'll adore the flowy feel of the fit-and-flare silhouette. Fit & FeaturesEyelet knit fabric with knit lining, Sleeveless square neckline, underbust seam, Adjustable spaghetti straps, Skater silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Look Eyelet Knit Skater Dress in White | Size: S | Knit Fabric
Be your own adorable muse in this sleeveless skater dress boasting a V-neckline and a ruffled skater silhouette. Complete the look with heels. Fit & FeaturesSheer lace fabric with knit lining, plenty of stretch, V-neckline with twist-front bust design, Adjustable spaghetti straps, V-shaped drop waist, Mini-length tiered ruffled skater silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Adorable Muse Ruffled Lace Skater Dress in Sage | Size: XS | Lace Fabric/Knit Fabric/Sheer Lace Fabric
Flirty And Adorable Strapless Lace Bow Floral Skater Dress in Natural
$26.97 $59.90
55% off
Flirty and adorable, this floral skater dress makes the sweetest impression at showers or birthdays! Featuring a sweetheart neckline with delicate lace trim and a charming bow, this dress is sure to turn heads. The padded bra cups provide a perfect fit, while the skater silhouette and mini-length hem add a touch of playfulness. Complete the look with earrings and strappy heels. Fit & FeaturesFloral print, chiffon fabric lined with woven, Strapless sweetheart neckline, Lace trim and bow, Padded bra cups, Back zipper and hook-eye closure, Skater silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flirty And Adorable Strapless Lace Bow Floral Skater Dress in Natural | Size: M | Chiffon
Summer Drop Waist Dresses
When the sun is high and the days are long, nothing says carefree confidence like a drop waist summer dress. This isn’t just a silhouette—it’s an attitude. With a fit that skims the body and flares out at just the right spot, a drop waist dress is your secret weapon for every sun-drenched adventure. Whether you’re heading out for brunch with your girls, dancing at a rooftop party, or just living your best life on a spontaneous road trip, this style keeps you feeling light, breezy, and totally unstoppable. The magic of a Windsor drop waist dress is in the way it moves with you—effortlessly, playfully, and with a hint of that signature flirty edge. It’s the kind of dress you slip into when you want to look put-together but still feel like you could break into a happy dance at any moment. And let’s be real: with its relaxed fit and playful vibe, it’s the ultimate choice for those days when you want to look like you tried (but didn’t have to try too hard).
Drop waist summer dresses also make for the sweetest gifts—think birthdays, graduations, or just-because moments when you want to make your bestie’s day. They’re the kind of piece that works for every vibe, from beachside hangs to city strolls, and they suit just about every body type. Gifting one is like handing over a little ticket to confidence, comfort, and endless compliments. And if you’re curating your own closet, don’t sleep on the versatility here. Style your drop waist number with sneakers and a crossbody for daytime errands, or swap in strappy heels and bold hoops for a night out that’s bound to turn heads. The best part? The breezy fit means you can move, groove, and soak up every second of sunshine without a care in the world. It’s a style that lets you live in the moment, laugh a little louder, and dance a little longer—because that’s what summer (and being a Windsor girl) is all about.
For those who crave a little extra inspo or want to see even more ways to rock this iconic silhouette, there’s a whole world of options waiting for you. From flirty ruffles and playful prints to sleek solids and subtle details, you’ll find a drop waist summer dress for every mood and every adventure. Ready to explore? Check out the collection of Drop Waist Casual Dresses and find your next ride-or-die look.