Casual Summer Maxi Dresses
Casual summer maxi dresses are your ticket to effortless style and easy-breezy confidence, no matter what’s on your agenda. Whether you’re brunch-bound or beach-dreaming, these flowy faves keep things cool while turning every sidewalk into a runway. Slip into the ultimate laid-back look and let those carefree vibes take over—because with casual summer maxi dresses, you’re always dressed for the best kind of trouble.
$42.90
A taupe strapless maxi dress in stretchy knit fabric featuring a vibrant floral print and side slit.
$19.97 $29.90 33% off
A strapless black floral maxi dress with a front slit and comfortable stretchy knit fabric.
$42.90
A pink tropical floral mesh maxi dress featuring a strapless neckline, high side slit, and form-hugging silhouette.
$22.97 $49.90 54% off
An airy pink mesh maxi dress with a bold floral print and adjustable spaghetti straps.
$39.90
A blue floral mesh maxi dress featuring a strapless neckline, form-hugging fit, and high side slit.
$44.90
A black one-shoulder tropical maxi dress with a ruffled slit and metal-accented strap.
$59.90
A white floral maxi dress with a ruffled silhouette and charming open tie back design.
$22.97 $49.90 54% off
A sage woven maxi dress featuring a flirty bust tie and flowy ruffled silhouette.
$54.90
A natural woven maxi dress featuring a flowy ruffled silhouette, square neckline, and spaghetti straps.
$26.97 $59.90 55% off
A chic black maxi dress with a flowy silhouette, V-neck, and trendy color block panels.
$44.90
A natural floral print maxi dress featuring a form-hugging silhouette and an open lace-up back.
$39.90
A strapless tropical maxi dress with a palm print, mesh fabric, and a high side slit.
$42.90
A natural-colored maxi dress featuring a bold floral print, mesh overlay, and a strapless, form-hugging silhouette.
$59.90
An ivory A-line maxi dress with gauze fabric, sheer lace insets, and a faux leather belt.
$26.97 $59.90 55% off
A chic black satin maxi dress featuring a halter neckline and a high front slit.
$44.90
A rust-colored one-shoulder maxi dress with a tropical print, side cutout, and high slit.
$44.90
A sultry black floral maxi dress with a V-neckline and form-hugging silhouette, perfect for vacations.
$19.97 $44.90 56% off
A pink floral maxi dress with a form-hugging bodice and flowy hem, perfect for special occasions.
$34.90
A light blue floral mesh maxi dress featuring a strapless neckline and curve-hugging, elegant silhouette.
$52.90
An orange floral mesh maxi dress featuring a V-neckline, spaghetti straps, and bold ruffled hem.
$49.90
A pink gauze maxi dress featuring a smocked waist, high front slit, and flowy A-line silhouette.
$56.90
A floral chiffon maxi dress with a flattering A-line silhouette and flowy hem in white.
$49.90
An airy ivory mesh maxi dress featuring a large floral print and an open cross-back strappy design.
$42.90
A taupe tropical print mesh maxi dress featuring a one-shoulder neckline, O-ring accent, and bust cutout.
$32.90
A black textured knit maxi dress featuring a strapless neckline, high side slit, and fitted silhouette.
$44.90
A black tropical print maxi dress featuring a sweetheart neckline, cutout bodice, and high side slit.
$39.90
A chic black crepe wrap dress with a plunging V-neckline and high front slit.
$46.90
A sultry brown maxi dress featuring a twist plunge V-neckline, cutout bodice, and ruffled slit.
$46.90
A bronze knit maxi dress featuring a trendy lace-up back and flattering bodycon silhouette.
$46.90
A black mesh maxi dress with a floral print, cowl neckline, and halter tie-back straps.
$32.90
A breezy white eyelet knit skater dress featuring a square neckline and double-layered flared skirt.
$42.90
A navy blue paisley skater dress with a halter V-neckline and playful tie-back design.
$22.97 $49.90 54% off
A pink floral mesh maxi dress with a mermaid silhouette and adjustable spaghetti straps.
$39.90
A sage knit maxi dress featuring a sweetheart neckline, buckle accent, cutout bodice, and high side slit.
$42.90
A rust floral skater dress in airy rayon with tie-back halter straps and an open back.
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Create a captivating entrance in this formal wrap dress for your next soiree. All eyes are on you in this stylishly chic long formal dress with a plunging V-neckline to perfectly display a sparkling rhinestone lariat or delicate layers of dainty necklaces. Fit & FeaturesCrepe fabric, moderate stretch, Asymmetrical wrap V-neckline, Adjustable spaghetti straps, Ruched detailing, slim-fit bodice, High front slit, floor-length wrap silhouette, Runs true to size, Where to Wear:Prom, black-tie weddings, and formal parties. Free Shipping on All Orders Over $75. | Windsor Sasha Formal High Slit Wrap Dress in Black | Size: XS | Rhinestone
Sultry and stunning, the Alisha formal dress will keep all eyes on you. With thin rhinestone detailed straps that give effortless sparkle and a curve-hugging silhouette, and an alluring high slit. Fit & FeaturesLightweight, breathable stretchy fabric, Sleeveless cowl neckline, Rhinestone detailed straps, High waist seam, Floor-length hem, form-fitting silhouette, high slit, Runs true to size, Where to Wear:Prom, glamorous evenings, dinner parties, weddings Free Shipping on All Orders Over $75. | Windsor Alisha Rhinestone Strap Formal Dress in Burgundy | Size: S | Stretchy Fabric/Rhinestone
Ella Cowl Neck Satin Dress in Orange
$19.97 $54.90
64% off
Enchant the room instantly in this gorgeous floor-length gown! Ella features a stunning sleeveless cowl neck, flattering high slit, and sleek spaghetti straps. Fit & FeaturesStretch satin lined fabric, Cowl neck, sleek spaghetti straps, Form-fitting silhouette, high-side slit, Floor-length hem, Runs true to size, Where to Wear:Prom, weddings, bridesmaids, fancy date nights, cocktail parties, engagement parties, rehearsal dinners Free Shipping on All Orders Over $75. | Windsor Ella Cowl Neck Satin Dress in Orange | Size: S | Satin Fabric
Charming Presence Strapless Slit Floral Maxi Dress in Black
$19.97 $29.90
33% off
Your presence will always be charming in this ditsy floral maxi dress at wedding showers, brunch, or casual parties! Adorned in a stunning disty floral print, this strapless dress features a ruffle trim neckline and padded bra cups for flattering support. The curve-hugging silhouette, front slit, and maxi-length hem create a captivating look, while the brushed knit stretchy fabric ensures comfort. Pair with earrings and strappy sandals. Fit & FeaturesDitsy floral print, Brushed knit stretchy fabric, Padded bra cups, Front slit, Curve-hugging silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Charming Presence Strapless Slit Floral Maxi Dress in Black | Size: M | Knit Fabric/Stretchy Fabric
Get ready to be on island time in this gorg tropical floral mesh maxi dress perf for vacay. Featuring a strapless neckline and high side slit, style with heels. Fit & FeaturesSheer mesh fabric with full-length knit lining, high stretch, Large tropical floral print, Strapless straight neckline, High-cut side slit, Maxi-length hem, Form-hugging silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Island Time Tropical Floral Mesh Maxi Dress in Pink | Size: L | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
Love Language Floral Print Mesh Maxi Dress in Pink
$22.97 $49.90
54% off
This airy mesh maxi dress speaks your love language designed with a bold floral print and long fitted silhouette. Style with mules for date night. Fit & FeaturesSheer mesh fabric with full-length knit lining, high stretch, Large floral print, V-neckline, Adjustable spaghetti straps, Maxi-length hem, fitted silhouette, Floral print placement may vary, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Love Language Floral Print Mesh Maxi Dress in Pink | Size: L | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
Gorgeous blooms dance across this floral maxi dress making every entrance statement worthy! Perfect for cocktail parties or dressy dinners, this strapless dress boasts a form-hugging fit, a high side slit allowing for movement, and a maxi-length hem. Complete the look with a clutch purse and heels. Fit & FeaturesFloral print, mesh fabric, stretchy knit lining, Strapless neckline, High side slit, Form-hugging fit, Runs true to size, Please note flower placement may vary, Free Shipping on All Orders Over $75. | Windsor Grandeur Blooms Strapless Slit Floral Maxi Dress in Blue | Size: S | Knit Fabric/Mesh Fabric/Mesh Fabric
A floral print adds to the dreamy charm of this flowy maxi dress boasting an open tie back design and ruffled silhouette perfect for beachside strolls or day parties. Fit & FeaturesFloral print, woven fabric, short woven lining, Sweetheart neckline with bust tie, Spaghetti straps, Open tie back design, Ruffled flowy silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sunshine Dream Open Tie Back Floral Maxi Dress in White | Size: L | Woven Fabric
Impress in this floral maxi dress showcasing a sleek strapless neckline and a column silhouette that flatters your figure. Style the dress with a choker. Fit & FeaturesStatement floral print, Mesh fabric lined with soft, stretch knit, Column silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Impressive Blossom Strapless Floral Maxi Dress in Black | Size: L | Mesh Fabric
Perfect for your vacay in Tulum, this one-shoulder tropical maxi dress was made for sunset dinners and dancing! Fit & FeaturesTropical print, smooth knit fabric with short stretchy lining, One-shoulder neckline, One shoulder strap with metal accents, Front ruffled slit, Bodycon silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor In Tulum One-Shoulder Tropical Maxi Dress in Black | Size: S | Knit Fabric
Casual Summer Maxi Dresses
Let’s be real—casual summer maxi dresses are the ride-or-die wardrobe staple every Windsor girl needs in her closet, ready for any adventure that pops up on the group chat. Whether you’re getting the crew together for a last-minute brunch, crashing an outdoor concert, or just living your best life on a spontaneous road trip, nothing says “I woke up like this” quite like the effortless flow and easygoing vibe of a maxi. These dresses are the ultimate confidence boosters, letting you sashay through your day with comfort, style, and a little bit of main character energy. Picture this: you, gliding through a sun-drenched farmer’s market, iced coffee in hand, catching every breeze in a maxi that moves with you. Or maybe you’re lounging on a rooftop, laughing with your girls, looking put together but feeling like you’re still in pajamas—because the right maxi dress does both. The magic is in the details: adjustable straps, breezy fabrics, and silhouettes that flatter every body, hugging where you want and skipping the rest. Maxi dresses are your secret weapon when you want to look like you tried (even if you didn’t).
Picking out the perfect casual summer maxi dress is all about embracing your mood and your plans. Feeling flirty? Go for a dress with a flouncy hem and a bold print that’s made for twirling on the dance floor or catching the sunset at your favorite hangout spot. Need something that goes from daytime errands to late-night tacos? A classic solid or subtle floral in a soft, stretchy fabric has you covered, literally and figuratively. These dresses are the ultimate blank canvas for your personal style—you can throw on sneakers and a denim jacket for a chill vibe, or dress things up with strappy sandals and layered jewelry when you’re feeling extra. And let’s talk gifting: if you’re searching for something that’ll have your bestie screaming with excitement or make your sister’s day, a casual maxi dress is the move. It’s thoughtful, versatile, and always the right size for making memories. Plus, with so many options out there, you can find a style that’s as unique as the person you’re shopping for.
If you’re craving more inspo or want to branch out from the classics, don’t sleep on the world of Sundress Maxi Dresses—it’s a whole vibe. Think sun-soaked days, spontaneous adventures, and dresses that make you feel like you’re on vacation, even if you’re just running errands. Maxi dresses are the ultimate go-anywhere, do-anything pieces, perfect for throwing in your weekender bag or slipping on after a dip in the pool. They’re made for the Windsor girl who’s always on the move, always ready for the next group selfie, and never afraid to stand out. So go ahead—let your style do the talking, dance through those golden hour plans, and know your maxi dress has your back every step of the way.