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.
$19.97 $44.90 56% off
A light blue skater dress with tie shoulder straps and a flattering drop waist seam.
$68.90
An ivory satin skater dress with floral jacquard, corset bodice, and lace-up back design.
$64.90
A white woven skater dress with lace trim, sweetheart neckline, and lace-up back for summer charm.
$39.90
A light blue lace mini dress featuring beaded spaghetti straps, sweetheart neckline, and pleated A-line silhouette.
$69.90
A floral ivory skater dress with a lace-up corset bodice and V-shaped drop waist.
$39.90
A pink strapless skater dress with a glitter knit fabric and tiered ruffled hem.
$19.97 $34.90 43% off
A charcoal skater dress with a ribbed knit top and tiered ruffled chiffon A-line silhouette.
$19.97 $42.90 53% off
A romantic white floral mini dress with lace trim and a lace-up back in cotton fabric.
$59.90
A chic yellow satin skater dress featuring a lace-up corset bodice and lace trim neckline.
$29.90
A flirty white skater dress featuring a strapless neckline and tiered eyelet knit design.
$19.97 $39.90 50% off
A chic black mini dress with a drop waist and pleated bubble hem for a flirty vibe.
$42.90
A white skater dress with tie-back halter straps and a flattering V-shaped drop waist.
$54.90
An ivory satin skater dress with a halter neckline, drop waist, and bubble hem for semi-formal events.
$49.90
An ivory floral skater dress with a corset bodice and flared hem, perfect for sunny occasions.
$69.90
A pink satin skater dress featuring a lace-up back, corset bodice, and bow tie shoulder straps.
$39.90
An ivory lace skater dress with an off-the-shoulder neckline and sheer long fitted sleeves.
$59.90
A black sequin skater dress with an open back and tie-back bow, perfect for parties.
$42.90
A red gingham skater dress with lace trim and button details for a charming spring look.
$46.90
An ivory woven A-line midi dress featuring lace-up details, smocked bust, and hidden side pockets.
$59.90
A pink woven mini dress featuring a tie-front design, pleated hem, and spaghetti strap ties.
$52.90
An ivory skater dress with puff sleeves, lace trim, and a playful bubble hem.
$46.90
An adorably chic taupe skater dress featuring a plaid print and strapless sweetheart neckline.
$39.90
A navy blue strapless mini dress featuring a tiered A-line silhouette and stretchy knit fabric.
$46.90
A blue floral eyelet skater dress with flutter sleeves, tiered A-line silhouette, and tie-back detail.
$69.90
An ivory skater dress with floral appliques, open back, and plunge V-neckline for whimsical elegance.
$49.90
A light blue striped woven skater dress featuring a square neckline, mini bow, and pleated drop waist.
$52.90
A strapless black mini dress featuring sheer lace, a drop waist, and tiered ruffled A-line silhouette.
$49.90
A strapless denim mini dress featuring ruffled trim, vertical seams, and a playful A-line silhouette.
$44.90
A strapless black knit mini dress featuring a drop waist and tiered ruffled asymmetric hem for flirty style.
$46.90
A vibrant yellow skater dress with a ruffled skirt, halter tie-back, and smocked high waist.
$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 breezy eyelet knit fabric and a charming tie-back detail.
$19.97 $44.90 56% off
A strapless black lace and chiffon skater dress with a corset bodice and ruffle trim neckline.
$64.90
An elegant black velvet skater dress with an off-the-shoulder neckline and pleated silhouette.
$46.90
An adorable white eyelet mini dress with a flirty tie-back and ruffled A-line silhouette.
$20.97 $46.90 55% off
A white floral skater dress featuring crisscross tie-back straps and a ruffled mini-length hem.
$52.90
A white lace skater dress featuring a scoop neckline, ruffle trim, and adjustable spaghetti straps.
$49.90
A yellow eyelet skater dress featuring a V-neckline, adjustable spaghetti straps, and a tie-back design.
$24.97 $54.90 55% off
A floral ivory skater dress with a halter V-neckline and voluminous silhouette for sunny days.
$59.90
An ivory A-line maxi dress with gauze fabric, sheer lace insets, and a faux leather belt.
$42.90
A navy blue paisley skater dress with a halter V-neckline and playful tie-back design.
$49.90
An A-line midi dress in natural woven fabric with a smocked bodice, pleats, and hidden pockets.
$46.90
A charming floral babydoll mini dress in natural with a flowy ruffled silhouette and smocked bust.
$38.90
A white striped mini dress featuring a strapless neckline, flirty cutout, and stretchy rib knit fabric.
$49.90
An olive green gauze skater dress featuring a tie-front, ruffled tiers, and adjustable spaghetti straps.
$44.90
A yellow skater dress featuring eyelet lace embroidery and a stretchy smocked bodice.
$34.90
An off-white sheer lace mini skort featuring a drop waist and tiered ruffled overlay with hidden shorts.
$42.90
A rust floral skater dress in breezy rayon with tie-back halter straps and an open back.
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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: M | 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: XS | 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 Ivory | Size: S | Satin Fabric
This skater dress was made for sunset happy hours this season! It features a sleeveless V-neckline, halter tie-back straps, an open back, a stretchy smocked high waist, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The lightweight twill fabric includes a woven lining. Style this short dress with espadrille sandals and a mini handbag. Fit & FeaturesSleeveless V-neckline, Halter tie-back straps, open back, Stretchy smocked high waist, Short skater skirt, tiered ruffled design, Fit and flare silhouette, Twill fabric, woven lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sunset Happy Hour Ruffled Skater Dress in Yellow | Size: M
Windsor Bling Fling Satin Rhinestone Skater Dress in Royal Blue
$20.97 $45.90
54% 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: L | 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
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 White | Size: L | Lace Fabric/Knit Fabric/Sheer Lace 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
Spring forward in the cutest skater dress showcasing a head-turning strappy tie-back and a flattering ruffled mini-length hem that'll swoon everyone! Fit & FeaturesWoven fabric with woven lining, Square neckline with bust tie, Spaghetti straps, Strappy tie-back design, Skater silhouette, Ruffled mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Spring Forward Strappy Back Skater Dress in Yellow | Size: L | Woven Fabric
Summer Drop Waist Dresses
When it comes to nailing that effortlessly chic vibe, nothing does it quite like a drop waist dress. There’s just something about that relaxed fit and playful silhouette that feels like a breath of fresh air—easy, breezy, and ready for whatever mischief you and your girls have planned. Whether you’re headed to a rooftop brunch, a downtown art crawl, or just want to turn the sidewalk into your personal runway, a windsor drop waist dress is your secret weapon for serving main character energy all day (and night) long. The beauty of this style is how it flatters every figure, skimming over curves and letting you move with total freedom. If you love a look that’s flirty without trying too hard, this is your new go-to. And let’s be real—when the temps are up and the sun is shining, the last thing you want is anything clingy. Drop waist dresses let you breathe, twirl, and dance without a care, making them a dreamy pick for everything from spontaneous road trips to laid-back backyard hangs.
Gifting a drop waist dress is basically giving someone the ultimate pass to fun and freedom. It’s the kind of gift that says, “I know you, I see you, and you deserve to feel amazing.” Perfect for birthdays, graduations, or just-because surprises, these dresses are a hit with besties, sisters, and anyone who loves a little flair in their wardrobe. The best part? They’re a blank canvas for personal style. Layer on bold jewelry, toss on a denim jacket, or slip into strappy sandals—the options are endless and the mood is always right. Shopping for yourself? You already know you’re about to make every mirror selfie next-level. And if you’re a planner (or a last-minute legend), drop waist dresses are clutch for those “what do I wear?!” moments, working for casual hangs and dressed-up nights alike. If you want to see even more ways to style this iconic silhouette, check out our Drop Waist Casual Dresses collection for inspo that’ll have you adding to cart before you can say “group chat outfit check.”
When you’re picking out your next windsor drop waist dress, think about what makes you feel unstoppable. Maybe it’s a lightweight fabric that moves with you, a color that pops against your skin, or a detail like a ruffled hem or a daring neckline. The drop waist shape is all about mixing comfort with a hint of drama—just enough to keep things interesting. If you’re planning to travel, these dresses are a dream to pack, rolling up small and coming out ready to slay. They’re also a lifesaver for those days when you need to go from coffee dates to late-night adventures without missing a beat. And because we know you’re not afraid to stand out, don’t be shy about picking bold prints or unexpected textures. Drop waist dresses are made for girls who love to play by their own rules, and every time you slip one on, you’re making a statement: confident, carefree, and always up for a little fun.