Daytime Casual Dresses
Ready to slay the day in effortless style? Our collection of daytime casual dresses is here to keep your vibe fresh and fabulous from brunch dates to impromptu shopping sprees. These dresses are all about that easy-breezy flair, perfect for strolling through the city or lounging at your favorite café. With a mix of playful prints and chic silhouettes, you'll find the perfect piece to match your mood and keep you looking effortlessly on point. Whether you're channeling boho vibes or minimalist chic, these daytime casual dresses have got you covered for every sunlit adventure.
$46.90
A vibrant yellow skater dress with a ruffled design, halter tie-back, and smocked high waist.
$20.97 $46.90 55% off
A white strapless skater dress with a ruched bodice and playful pleated hem.
$46.90
An ivory striped midi dress with cutouts, adjustable straps, and dual side slits for casual elegance.
$52.90
A white eyelet lace skater dress featuring a scoop neckline and ruffled mini-length hem.
$44.90
A taupe paisley skater dress with a halter V-neck and flowy mini-length hem.
$49.90
An ivory floral skater dress with a corset bodice and flared hem, perfect for sunny occasions.
$34.90
A strapless white floral mini dress with an A-line silhouette and eyelet fabric for casual occasions.
$44.90
A glamorous blue satin skater dress featuring a lace-up back and adjustable spaghetti straps.
$36.90
An elegant sage off-the-shoulder midi dress in stretchy knit fabric with a flattering bodycon fit.
$64.90
A sage woven skater dress with a lace-up back and asymmetric drop-waist for a sweet summer look.
$39.90
A brown knit midi dress with ruched detailing and an off-the-shoulder neckline for casual elegance.
$38.90
A white eyelet knit skater dress featuring a sleeveless square neckline and adjustable spaghetti straps.
$48.90
A breezy white eyelet knit mini skater dress with a flirty tie-back and ruffled hem.
$35.90
A natural-colored sleeveless mini dress in stretchy knit with a faux wrap-front and tie detail.
$44.90
A white floral skater dress with a strappy tie-back and ruffled mini-length hem.
$59.90
A white woven maxi dress featuring a floral print, open tie back, and ruffled silhouette.
$19.97 $44.90 56% off
A white eyelet lace mini dress with puff sleeves and a ruffled hem for flirty occasions.
$22.97 $49.90 54% off
A sage woven maxi dress featuring a flirty bust tie and flowy ruffled silhouette.
$19.97 $32.90 39% off
A brown knit halter skater dress with ruched waist and a flirty double-layered skirt.
$44.90
A black floral skater dress featuring a corset bodice and bubble hem for a flattering silhouette.
$19.97 $30.90 35% off
A chic black A-line mini dress with a tie-back design and cap sleeves, perfect for casual outings.
$9.97 $38.90 74% off
A brown knit bodycon midi dress with flare cuff sleeves and a V-neckline for chic occasions.
$46.90
A charming floral babydoll mini dress in natural with a flowy ruffled silhouette and smocked bust.
$28 $39.90 30% off
A khaki woven midi dress featuring a smocked bodice, ruffled hem, and dual spaghetti straps.
$19.97 $34.90 43% off
A charcoal skater dress with a ribbed knit top, V-shaped drop waist, and tiered chiffon ruffles.
$24.97 $54.90 55% off
A floral ivory skater dress with a halter V-neckline and voluminous silhouette for sunny days.
$19.97 $35.90 44% off
A strapless taupe midi dress with a tropical print and flared hem, perfect for vacations.
$44.90
A strapless pink crepe mini dress with an A-line silhouette perfect for polished occasions.
$42.90
A navy blue paisley skater dress with a halter V-neckline and playful tie-back design.
$19.97 $42.90 53% off
A charming ivory midi dress with a ditsy floral print and lace-trimmed sweetheart neckline.
$19.97 $24.90 20% off
An olive bodycon midi dress with cap sleeves, a cutout back, and stretchy rib knit fabric.
$44.90
A yellow skater dress featuring eyelet lace embroidery and a stretchy smocked bodice.
$59.90
An effortlessly pretty chiffon midi dress with a floral print, ruffled tiers, and smocked details.
$44.90
A sultry black floral maxi dress with a V-neckline and form-hugging silhouette, perfect for vacations.
$46.90
A black floral halter midi dress with a flowy A-line silhouette and tie-back design.
$49.90
A light blue chiffon midi dress with floral print, puff sleeves, and a chic high front slit.
$52.90
A strapless ivory chiffon skater dress featuring a ruffled silhouette and stretchy smocked bodice.
$26.90
A taupe plaid mini dress with a V-neckline, spaghetti straps, and a side slit.
$49.90
A black rib knit mini dress with a halter neckline and playful skater silhouette.
$52.90
An ivory skater dress with puff sleeves, lace trim, and a playful bubble hem.
$36.90
A black ribbed knit halter mini dress with a skater silhouette, perfect for festivals or casual outings.
$47.90
A lustrous blue satin skater dress with a sleeveless cowl neckline and spaghetti straps.
$38.90
An elegant natural lace dress with a sleeveless square neckline and flattering A-line silhouette.
$38.90
A denim mini dress with a sleeveless square neckline, pleated bust, and A-line silhouette.
$46.90
A denim skater mini dress with a sweetheart neckline and chiffon lace trim for festival flair.
$35.90
A pink sleeveless bodycon midi dress with stretchy knit fabric and a flattering square neckline.
$69.90
A charming ivory floral skater dress featuring a lace-up corset bodice and sheer lace trims.
$54.90
An ivory floral satin dress with a lace-up back and flirty A-line silhouette.
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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
Daytime Casual Dresses
Ready to hit refresh on your closet? Daytime casual dresses are basically the MVPs of your wardrobe—those effortless pieces you toss on when you want to look cute but keep it low-key. Think of that moment when your bestie texts, “Brunch in 30?” and you’re still in your pajamas—yeah, that’s when these dresses save the day. Windsor casual dresses are made for girls who want to look put-together without the drama, whether you’re running errands, meeting up for an impromptu coffee date, or just living your best life out and about. Picture yourself gliding through a sun-drenched afternoon, iced latte in hand, feeling breezy and unstoppable in a perfectly-fitted day dress. These are the looks that work for every vibe—laid-back, flirty, or somewhere in between. And honestly, there’s nothing like a dress that does the heavy lifting for you, making you feel confident and comfy from sunrise to sunset.
Daytime dresses are also the secret weapon for those “I have nothing to wear” days. You know the drill: you open your closet, stare into the abyss, and somehow, a cute day dress is always the answer. They’re easy to style—add sneakers for a stroll in the park, slip on sandals for a rooftop lunch, or layer with a denim jacket when you want a touch of edge. They make the best gifts, too—think birthdays, graduations, or just because your BFF deserves a little treat. Daytime casual dresses are perfect for anyone who wants their style to keep up with their plans, whether you’re the friend who’s always organizing the group hang or the one who loves a spontaneous adventure. And if you’re into twirling through your day with confidence, check out styles that flatter every figure, from flowy A-lines to curve-hugging fits. There’s something undeniably empowering about finding that dress that feels like it was made just for you.
If you’re ready to level up your daytime casual game, don’t sleep on the power of a midi length—trust us, the versatility is next-level. For those who crave a little extra coverage or want a look that transitions seamlessly from day to night, explore our curated selection of Daytime Midi Dresses. Whether you’re gifting yourself or someone you love, these dresses are the ultimate confidence boost, perfect for making every day feel like a main character moment. So go ahead, embrace the bold prints, soft pastels, and playful details that make Windsor casual dresses a must-have. With the right daytime dress, you’re always ready for whatever the day throws your way—coffee runs, market strolls, spontaneous selfies, and all the little adventures in between.