Drop Waist Casual Dresses
Get ready to turn heads and drop jaws with our fabulous collection of drop waist casual dresses! These effortlessly chic pieces are perfect for those days when you want to strut your stuff with a little extra flair. Imagine twirling through your day with the carefree vibe of a fashionista who knows how to keep it cool and stylish. Whether you're brunching with the squad or catching rays at a park picnic, these dresses have your back, making sure you look fabulous while keeping it casual. So go ahead, embrace that laid-back glam and let your inner fashion icon shine!
$52.90
An ivory skater dress with puff sleeves, lace trim, and a playful bubble hem.
$38 $46.90 19% off
A chic black and white pinstripe romper with floral lace straps and a pleated skater skirt.
$64.90
A sage skater dress with a lace-trimmed sweetheart neckline and adjustable lace-up back.
$69.90
A charming ivory floral skater dress featuring a lace-up corset bodice and sheer lace trims.
$39.90
A pink strapless skater dress with a glitter knit fabric and tiered ruffled hem.
$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.
$20.97 $46.90 55% off
An ivory chiffon skater dress featuring a smocked bodice, cutout accent, and breezy long sleeves.
$19.97 $34.90 43% off
A charcoal skater dress with a ribbed knit top and tiered ruffled chiffon A-line silhouette.
$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.
$46.90
A chic black chiffon skater dress featuring a lace halter neckline and mesh corset bodice.
$54.90
An ivory satin skater dress with a halter neckline, drop waist, and bubble hem for semi-formal events.
$19.97 $44.90 56% off
A light blue skater dress with tie shoulder straps, lace-up back, and flattering drop waist seam.
$49.90
An ivory floral skater dress with a corset bodice and flared hem, perfect for sunny occasions.
$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 adorably chic taupe skater dress with a plaid print and strapless sweetheart neckline.
$39.90
An ivory lace skater dress with an off-the-shoulder neckline and sheer long fitted sleeves.
$19.97 $59.90 67% off
A strapless black taffeta skater dress with a sweetheart neckline and chic drop waist seam.
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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
Drop Waist Casual Dresses
When it comes to bringing that effortless, “I woke up like this” energy to your everyday style, nothing hits quite like a drop waist casual dress. There’s just something about that relaxed fit and flirty silhouette that makes you want to twirl through your to-do list, grab a latte with your girls, and maybe even say yes to a spontaneous road trip—just because you’re feeling yourself. Whether you’re running errands, brunching at your favorite spot, or plotting your next adventure, the casual drop waist dress is your ride-or-die. The loose, lower waistline means you’ll never have to sacrifice comfort for style (or vice versa), and the way it skims your curves? Chef’s kiss. It’s the ultimate confidence booster, perfect for those days when you want to look put-together without trying too hard. Think of it as your wardrobe’s secret weapon: throw it on, add some chunky sneakers or strappy sandals, and you’re instantly serving main character energy.
Gifting a drop waist dress casual look is pretty much the definition of “best friend energy.” It’s the kind of piece that works for everyone—your sister who’s always on the go, your BFF who lives for cute coffee shop dates, or even your mom who deserves to feel fabulous on her day off. Because the drop waist silhouette is so universally flattering, it’s an easy win for birthdays, graduations, or just-because surprises. And let’s be real: nothing says “I love you and your style” like helping someone feel like the best version of themselves. When you’re picking out a windsor drop waist dress, think about the little details that make it pop—like playful ruffles, breezy fabrics, or a bold print that matches her vibe. You’ll want to consider how she’ll wear it, too. Is she all about layering with a denim jacket and boots, or does she keep it simple with a delicate necklace and a swipe of lip gloss? Whatever her mood, a drop waist casual dress fits right in, ready to be dressed up or down for anything on her calendar.
The beauty of a drop waist dress is that it’s not just a trend—it’s a lifestyle. It’s for the girl who’s always on the move, the one who dances in her kitchen, laughs a little too loud, and knows that comfort and confidence are non-negotiable. You can slip into a windsor drop waist dress for a laid-back lunch date, a sunset walk, or a last-minute invite that pops up in your group chat. And if you’re feeling a little extra (because why not?), you can always take your love for this silhouette to the next level with something more glam—check out our Drop Waist Gowns for those moments that call for a little drama. The drop waist dress is your go-to for making memories, turning heads, and living your best life—no matter where the day takes you. So go ahead, give your closet the upgrade it deserves and let your style do the talking. You’ve got this, babe.