Casual Vacation Dresses
Jet-setting off to a dreamy destination or planning a spontaneous weekend getaway? Our collection of casual vacation dresses has got your back, ready to make every moment feel like a sun-kissed adventure. Think breezy fabrics, vibrant colors, and effortlessly chic styles that scream "vacay mode activated!" Whether you're strolling through cobblestone streets or lounging by the beach, these dresses are your ultimate travel buddies, keeping you stylishly cool and confidently carefree. So go ahead, pack your bags and slip into something fabulous—your next unforgettable escape awaits!
$36.90
An elegant off-the-shoulder natural knit midi dress with a bodycon fit and flared hem.
$46.90
A vibrant yellow skater dress with a ruffled skirt and halter tie-back straps for sunset outings.
$19.97 $32.90 39% off
A strapless yellow mini dress with ruched sides and a playful ruffled hem in knit fabric.
$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 gold metallic knit maxi dress featuring a plunge cowl halter neckline and adjustable strappy open back.
$20.97 $46.90 55% off
An abstract red knit maxi dress featuring a cowl neckline, hoop trims, strappy back, and high side slit.
$59.90
An ivory A-line maxi dress featuring 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.
$19.97 $28.90 31% off
A breezy black midi dress featuring gauze fabric, a V-neck, adjustable straps, and hidden side pockets.
$54.90
A denim woven maxi dress featuring a flowy ruffled silhouette, square neckline, and spaghetti straps.
$9.97 $42.90 77% off
A slate A-line mini dress with a V-neckline and ruffled hem in soft knit fabric.
$34.90
A chic brown strapless maxi dress with a high slit and flattering bodycon silhouette.
$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 stretchy smocked bodice.
$49.90
A brown mesh maxi dress featuring a bold floral print, drapey cowl halter neckline, and curve-hugging fit.
$20.97 $46.90 55% off
An olive green gauze skater dress featuring flowy sleeves, V-necklines, and a chic cutout bodice.
$9.97 $37.90 74% off
An ivory floral bodycon mini dress featuring a strapless neckline and flirty ruffled hem.
$9.97 $46.90 79% off
A blue gauze skater dress featuring a halter neckline, cutout bodice, and ruffled mini hem.
$19.97 $39.90 50% off
A natural paisley-print maxi dress in mesh with a bodycon fit, square neckline, and high side slit.
$9.97 $49.90 80% off
A strapless ivory skater dress with a floral print and flirty ruffled hem.
$26.90
A taupe plaid mini dress with a V-neckline, spaghetti straps, and a bodycon silhouette.
$39.90
A brown tropical floral mesh midi dress featuring a strapless neckline, ruched sides, and flowy sheer hem.
$9.97 $49.90 80% off
A strapless black woven midi dress featuring a color block bodice, flowy hem, and hidden pockets.
$25 $34.90 28% off
A grey plaid strapless mini dress with a pleated hem and form-hugging knit fabric.
$32.90
An ivory striped ribbed knit mini dress with an off-the-shoulder neckline and long fitted sleeves.
$19.97 $35.90 44% off
A white knit mini dress featuring a strapless neckline, side cutout with hardware, and bodycon silhouette.
$36.90
A denim satin mini dress with a ruched wrap silhouette and spaghetti straps for a chic look.
$32.90
A sage satin off-the-shoulder mini dress with a flattering A-line silhouette for special occasions.
$46.90
A brown woven midi dress with a ditsy floral pattern, corset bodice, and high front slit.
$68.90
An ivory satin skater dress with floral jacquard, corset bodice, and lace-up back for chic elegance.
$35.90
A pink sleeveless bodycon midi dress with a square neckline and stretchy knit fabric.
$49.90
A lavender skater dress with glitter mesh, sheer sleeves, and a fit and flare silhouette.
$36.90
A chic black mini dress with a pleated cowl neckline and flowy A-line silhouette.
$21.97 $42.90 49% off
An effortlessly chic brown ribbed knit mini dress with long sleeves and a scoop neckline.
$39.90
A sheer white crochet knit cover-up dress with long sleeves, plunge neckline, and chic hoop insert.
$42.90
An abstract print maxi dress with a ruched bodycon silhouette and sheer off-the-shoulder sleeves.
$38.90
A vibrant pink mini dress featuring a leopard snake print, mesh fabric, side cutout, and ruffled slit.
$39.90
An ivory lace skater dress with an off-the-shoulder neckline and sheer long fitted sleeves.
$29.90
A trendy brown striped knit mini dress with a mock neckline and long fitted sleeves.
$44.90
A green mini dress with a sleeveless square neckline, cap-like sleeves, and flattering ruching.
$36.90
A cozy heather grey ribbed knit mini dress with an off-the-shoulder neckline and A-line silhouette.
$9.97 $56.90 82% off
A floral chiffon romper in natural with a strapless neckline and flattering drop waist seam.
$6.97 $29.90 77% off
A taupe ribbed knit bodycon mini dress with a scoop neckline and spaghetti straps.
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This adorable strapless A-line mini dress is so your vibe! Designed with a stretchy lined knit fabric, it features a strapless straight-across neckline, chic pleated detailing at the bust, and a flirty flowy A-line silhouette on the mini-length hem. Style for a girl's night with statement earrings and strappy mules. Fit & FeaturesStretchy knit fabric with knit lining, Strapless straight neckline, no-slip strip, Pleated bust, A-line fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Your Vibe Strapless A-line Mini Dress in Light Blue | Size: L | Knit Fabric
Bring on the cute attitude in this ponte mini skort brings featuring a flattering high-rise waist, and a skirt overlay designed with dual front slits along the form-hugging fit. Fit & FeaturesSmooth ponte knit fabric, minimal stretch, High-rise waist, Skirt overlay, dual front slits, Form-hugging silhouette, Mini-length hem, Shorts lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cute Attitude Ponte Slit Mini Skort in Black | Size: L | Knit Fabric
A fashionista like you will adore this basic mini skirt for creating your day and night looks! Featuring an elasticized high-rise waistband, bodycon silhouette, and a flirty front hem slit on stretchy and smooth knit fabric. Style with a corset top and heels. Fit & FeaturesHigh-rise elasticized waistband, Bodycon silhouette, Front hem slit, Mini-length hem, Stretchy and smooth knit fabric, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Get Down With Basic Slit Mini Skirt in Black | Size: XS | Knit Fabric
This satin mini dress will be your favorite for celebrations, events, and date nights! Sleek and smooth satin shapes this off-the-shoulder dress, which features a flattering A-line silhouette perfect for styling with heels. Fit & FeaturesSmooth and sleek satin fabric, stretchy knit lining, Off-the-shoulder neckline, Short sleeve cuffs, A-line silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Classics Lover Off-The-Shoulder Satin A-Line Mini Dress in Pink | Size: S | Knit Fabric/Satin Fabric
A true showstopper of a mini dress perfect for adding a touch of sparkle to any occasion. The short-length rhinestone dress features a square neckline and adjustable spaghetti straps, while the A-line silhouette flatters your figure down to the uneven-cut hem. Complete the look in platform sandals for a dressy night out! Fit & FeaturesSleeveless square neckline, Adjustable spaghetti straps, Back zipper and hook-eye closure, A-line silhouette, Mini-length hem, uneven cut design, Rhinestone-embellished, mesh fabric, stretchy knit lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sparkling Perfection Rhinestone A-Line Mini Dress in Pink | Size: XS | Knit Fabric/Rhinestone/Mesh Fabric
Capture all the attention with your sultry allure in the Paige rhinestone formal bodycon mini dress! She features a sleeveless cowl neckline, adjustable spaghetti straps for a customized fit, all-over rhinestone embellishments for that total glam girl vibe, a mini-length hem, and a bodycon silhouette to hug your gorgeous curves. The slinky knit fabric offers plenty of stretch. Style this mini dress with metallic heels for your next dressy night out! Fit & FeaturesSleeveless cowl neckline, Adjustable spaghetti straps, All-over rhinestone embellishments, Mini-length hem, bodycon silhouette, Slinky knit fabric, full-length knit lining, plenty of stretch, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Paige Rhinestone Formal Bodycon Mini Dress in Light Blue | Size: M | Knit Fabric/Rhinestone
This chic side slit knit mini skirt will give you a fabulous fit and become a favorite in your closet! The ponte knit fabric offers a structured fit with moderate stretch. The high waist features an elasticized waistband for comfortable wear, while the mini-length hem and side slit accent will give that sultry flair. The bodycon silhouette will hug your gorgeous curves. Style this mini skirt with a basic bodysuit and ankle booties for happy hour. Fit & FeaturesPonte knit fabric, moderate stretch, High-rise elasticized waist, Mini-length hem, Asymmetric seam, side slit, Bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fabulous Fit Side Slit Knit Mini Skirt in Black | Size: L | Knit Fabric
Windsor Brenda Low Back Bow Taffeta Skater Dress in Black
$19.97 $64.90
69% off
Chat, dance, and twirl the night away in the Brenda taffeta skater dress! The short dress is ready to party with a voluminous silhouette and a stunning low-cut back with a statement bow. Fit & FeaturesTaffeta fabric lined with tulle, stretchy knit fabric, Tank shoulder straps, Low back with bow, Skater silhouette, Short-length hem, Runs true to size, Where to Wear:Prom, brides, weddings, bridesmaids, fancy date nights, dinner parties, cocktail events Free Shipping on All Orders Over $75. | Windsor Brenda Low Back Bow Taffeta Skater Dress in Black | Size: XS | Knit Fabric
A sassy mini dress to slip on when the sun goes down and the beat is calling you to the dancefloor! This dress is featured in a sultry bodycon silhouette with a halter neckline accented with hoop inserts. Fit & FeaturesAbstract print, stretchy knit fabric, Cowl halter neckline, hoop accents, Bodycon silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sun Goes Down Halter Abstract Bodycon Mini Dress in Brown | Size: S | Knit Fabric
Windsor Here Comes The Sun Strapless Ruffled Mini Dress in Yellow
$19.97 $32.90
39% off
Here comes the sun and you radiating trendy vibes in this strapless mini dress perf for casual plans! The ruched sides and ruffled hem add a playful touch to the bodycon silhouette. Fit & FeaturesDouble-lined brushed knit fabric, moderate stretch, Strapless straight neckline, Ruched side seams, Bodycon silhouette, Mini-length tiered ruffled hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Here Comes The Sun Strapless Ruffled Mini Dress in Yellow | Size: L | Knit Fabric
Casual Vacation Dresses
Ready to live your best life, suitcase in one hand and iced coffee in the other? Let’s talk about the magic of casual vacation dresses—the ultimate sidekick for every getaway, from spontaneous road trips to that long-awaited island escape. Picture this: you, stepping off the plane or out of the car, feeling fresh, flirty, and totally unbothered by wrinkly, fussy outfits. That’s the energy a windsor casual dress brings to your vacay wardrobe. These dresses are all about effortless style and comfort, letting you slay the day from sunrise mimosas to late-night beach strolls. They’re the kind of pieces you can toss in your bag and forget about until you’re ready to throw one on and instantly look put together—no steamer, no stress, just pure confidence. Whether you’re snapping pics for the ‘gram, exploring cute local spots, or just vibing poolside with your crew, a casual vacation dress is your golden ticket to looking and feeling like the main character, every single day.
Gifting a casual vacation dress? Major bestie points incoming. These dresses are the ultimate “thinking of you” present for your ride-or-die, your sister, or that friend who’s always booking her next adventure. They’re the answer for birthdays, bachelorette trips, or just because—you know she’ll wear it on repeat. And let’s be real: nothing says “I love you” like giving someone the power to pack light and still look fire. When you’re choosing the perfect windsor casual dress, think about what makes her feel unstoppable. Flowy silhouettes that catch the breeze, playful prints that match her energy, and soft, breathable fabrics that keep her cool while she’s out chasing sunsets. Dresses with adjustable straps, smocked bodices, or tie waists are always a win—they flex with her style, whether she’s craving a laid-back look or ready to spice things up for dinner in a new city.
If you’re all about collecting memories (and compliments), these dresses are a must. They’re made for mixing and matching with everything from sneakers and sandals to statement jewelry and oversized sunnies. And when you’ve got a closet full of casual vacation dresses, outfit planning is basically a non-issue. Just grab your favorite, slip it on, and you’re ready for whatever adventure comes your way. No more overthinking, no more “I have nothing to wear” panic—just pure, carefree vibes. If you’re feeling inspired to level up your getaway wardrobe, or searching for the perfect gift that’ll leave her speechless, check out our curated collection of Women's Vacation Dresses. Your next iconic look is waiting, and trust us, you’re about to make every moment unforgettable.