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.
$9.97 $49.90 80% off
A strapless black woven midi dress featuring a color block bodice, flowy hem, and hidden pockets.
$36.90
An elegant sage off-the-shoulder midi dress in stretchy knit fabric with a flattering bodycon fit.
$44.90
A glamorous blue satin skater dress featuring a lace-up back and adjustable spaghetti straps.
$46.90
A vibrant yellow skater dress with a ruffled design, halter tie-back, and smocked high waist.
$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.
$32.90
A breezy white eyelet knit skater dress featuring a square neckline and double-layered flared skirt.
$46.90
A navy blue strapless mini skater dress in stretchy poplin with a ruched bodice and pleated hem.
$44.90
A strapless pink crepe mini dress with an A-line silhouette perfect for polished occasions.
$54.90
A denim woven maxi dress featuring a flowy ruffled silhouette, square neckline, and spaghetti straps.
$42.90
A navy blue paisley skater dress with a halter V-neckline and playful tie-back design.
$19.97 $28.90 31% off
A breezy black midi dress featuring gauze fabric, a V-neck, adjustable straps, and hidden side pockets.
$19.97 $42.90 53% off
A rust floral skater dress in airy rayon with tie-back halter straps and an open back.
$44.90
A sultry black floral maxi dress with a V-neckline and form-hugging silhouette, perfect for vacations.
$44.90
A taupe paisley skater dress with a halter V-neck and flowy mini-length hem.
$20.97 $46.90 55% off
An olive green gauze skater dress featuring V-neck cutouts, flowy sleeves, and a breezy silhouette.
$9.97 $46.90 79% off
A blue gauze skater dress featuring a halter neckline, cutout bodice, and ruffled mini hem.
$39.90
A brown tropical floral mesh midi dress featuring a strapless neckline, ruched sides, and flowy sheer hem.
$49.90
An airy white eyelet skater dress featuring a lace-up bust, lace trim, and adjustable tank straps.
$26.90
A taupe plaid mini dress with a V-neckline, spaghetti straps, and a side slit.
$52.90
An ivory skater dress with puff sleeves, lace trim, and a playful bubble hem.
$38.90
A denim mini dress with a sleeveless square neckline, pleated bust, and A-line silhouette.
$46.90
A chic black bodycon midi dress with a square neckline and stretchy double-lined knit fabric.
$54.90
An ivory floral satin dress with a lace-up back and flirty A-line silhouette.
$59.90
A white satin wrap midi dress with a sleeveless cowl neckline and high-side slit.
$19.97 $39.90 50% off
A natural paisley-print maxi dress in mesh with a bodycon fit, square neckline, and high side slit.
$36.90
A black nylon mini dress featuring a fitted A-line silhouette, square neckline, and hidden shorts.
$44.90
A green mini dress with a sleeveless square neckline, cap-like sleeves, and ruched detailing.
$89.90
A light blue woven A-line dress featuring a sweetheart neckline, lace trim, and hidden side pockets.
$6.97 $29.90 77% off
A taupe ribbed knit bodycon mini dress with a scoop neckline and spaghetti straps.
$42.90
A black knit midi dress featuring a front-tie bust, underbust cutout, and high front slit.
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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
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: S | Woven Fabric
Windsor Thriving Blooms Corset Floral Slit Midi Dress in Black
$20.97 $46.90
55% off
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: S | 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: M | Knit Fabric
Create a cute picturesque 'fit in this corset A-line midi dress! The corset bodice and lace-up back add a touch of allure to the sweet silhouette. Fit & FeaturesWoven fabric lined with stretchy knit, Sweetheart neckline, tie-front detail, Thin adjustable straps, Corset bodice, lace-up back, High waist seam, Midi-length A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Picturesque Cutie Corset Lace-Up A-Line Midi Dress in Light Blue | Size: L | Woven Fabric
Show off your smooth moves in this strapless bodycon midi dress perfect for dressing up or down for any occasion! Fit & FeaturesRib knit fabric, sewn-in knit lining, moderate stretch, Strapless neckline, Side slit, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Smooth Talker Strapless Bodycon Midi Dress in Light Blue | Size: L | Knit Fabric
This sleeveless ribbed knit midi dress features a striking V-neckline and bodycon fit with a front slit detail for movement. Perfect for layering with a jacket and heels. Fit & FeaturesStretchy ribbed knit fabric, V-neckline, Spaghetti straps, Front slit, Midi-length bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Toasty Sweetheart V-Neck Bodycon Knit Midi Dress in Chartreuse | Size: L | Knit Fabric
The perfect chic sleeveless midi dress for grabbing dinner downtown! Crafted from smooth knit fabric, this crew neck dress boasts curve-accentuating ruched seams along the bodycon silhouette and a sleek midi-length hem. Pair with kitten heels and a clutch. Fit & FeaturesSmooth knit fabric, stretchy knit lining, Sleeveless crew neck, Side ruched seams, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Dinner Downtown Sleeveless Ruched Midi Dress in Brown | Size: S | Knit Fabric
Show off pretty vibes in this adorable layered skater dress made with breezy eyelet knit fabric. Pair with sneakers for a cute casual look or wedges for a dressier style. Fit & FeaturesStretchy sheer eyelet knit fabric, partial knit lining, Square neckline, Spaghetti straps, Double-layered skater skirt, Short fit-and-flare silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Pretty Vibes Eyelet Knit Layered Skater Dress in White-2 | Size: L | Knit Fabric
Windsor Petit Blooms Floral Eyelet Midi Dress in Ivory
$9.97 $30.90
68% off
Dainty floral makes this eyelet midi dress the cutest spring-to-summer style! Fit & FeaturesDainty floral print, eyelet fabric, sewn-in knit lining, Strapless neckline, Bodycon fit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Petit Blooms Floral Eyelet Midi Dress in Ivory | Size: XS | Knit Fabric
Daytime Casual Dresses
When it comes to curating your closet with looks that totally get your vibe, nothing beats the effortless energy of casual dresses for daytime. These are the pieces you reach for when you want to look cute but feel comfy, whether you’re running to grab an iced latte before class, hitting up a last-minute lunch with your besties, or just living your main character life on a spontaneous road trip. Windsor casual dresses are all about that perfect blend of laid-back and put-together—think breezy cottons and linens that let your skin breathe, soft jersey knits that move with you, and playful prints that basically scream “good mood, incoming.” You’ll find styles with smocking that hugs in all the right places, flutter sleeves that flirt with the breeze, and tiered skirts that twirl like a dream. These dresses are made for real life: easy to throw on, easy to dress up or down, and always ready for whatever your day throws at you.
Picking out a daytime dress is kind of like choosing your own adventure. Maybe you’re in the mood for a daytime mini dress that keeps things flirty and fun—perfect for that rooftop brunch or a day of window shopping. Or maybe you want something a little more polished, like a midi dress that gives you that just-right balance of coverage and freedom to move. Midi and maxi lengths are especially clutch when you want a touch more drama or need to transition from a chill morning to an afternoon meet-up without missing a beat. The magic of daytime dressy casual is that you can style these looks with literally anything: sneakers for a sporty twist, sandals for a beachy feel, or wedges if you’re feeling a little extra. Add a tote bag big enough for your essentials (and maybe a snack), some oversized sunnies, and a swipe of lip gloss—suddenly, you’re the girl everyone wants to know. And if you’re shopping for someone else, trust: a cute, comfy dress is basically the universal love language. They make the sweetest gifts for birthdays, graduations, or just because your bestie deserves to feel like a ten.
Let’s be real, the right casual dress can take you from running errands to catching golden hour with zero outfit changes needed. Look for those little details that make a dress feel like you—maybe it’s a shirtdress with a cinched waist that gives you that “borrowed from the boys but made it chic” vibe, or a smocked bodice that makes every body type look fire. If you’re all about options, check out our Daytime Midi Dresses for that sweet spot between casual and elevated. And don’t sleep on the power of a fresh floral print or a pop of color to instantly boost your mood (and your Insta feed). Whether you’re gifting a daytime dress to your ride-or-die or treating yourself to a wardrobe refresh, these pieces are designed to keep up with your wildest plans and your chillest days. So go ahead, live in the moment—your closet’s got your back.