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.
$38.90
A white sleeveless ribbed knit midi dress with a V-neckline and chic high front slit.
$64.90
A white woven skater dress featuring a lace-up back, ruched bust, and tiered A-line silhouette.
$19.97 $29.90 33% off
A strapless black floral maxi dress with a front slit and comfortable stretchy knit fabric.
$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 with adjustable straps and a flowy fit-and-flare silhouette.
$46.90
A sultry brown maxi dress featuring a twist plunge V-neckline, cutout bodice, and ruffled slit.
$48.90
A breezy white eyelet knit mini skater dress with a flirty tie-back and ruffled hem.
$32.90
A strapless red mini dress with ruched sides and a playful ruffled hem in brushed knit fabric.
$35.90
A natural-colored sleeveless wrap mini dress in stretchy knit fabric with a form-hugging fit.
$44.90
A playful ivory knit mini dress with long sleeves, cutout details, and a bodycon fit.
$34.90
A black abstract floral mini dress with a cowl halter neckline and ruffled slit design.
$44.90
A white floral skater dress with a strappy tie-back and ruffled mini-length hem.
$20.97 $46.90 55% off
A white strapless skater dress with a ruched bodice and playful pleated hem.
$59.90
A white woven maxi dress featuring a floral print, open tie back, and ruffled silhouette.
$44.90
A black one-shoulder tropical maxi dress with a ruffled slit and metal-accented strap.
$46.90
An ivory striped midi dress with cutouts, adjustable straps, and dual side slits for casual elegance.
$19.97 $34.90 43% off
A strapless white bodycon mini dress with a bold floral print and sheer mesh overlay.
$36.90
A strapless black mini dress with a floral print and flattering bodycon fit in stretchy knit fabric.
$19.97 $32.90 39% off
A brown knit halter skater dress with ruched waist and flirty double-layered skirt.
$19.97 $42.90 53% off
A slate A-line mini dress with a V-neckline and ruffled hem in soft knit fabric.
$28 $39.90 30% off
A khaki woven midi dress with a smocked bodice, square neckline, and ruffled A-line silhouette.
$44.90
A taupe paisley skater dress featuring a halter V-neck and stretchy smocked bodice.
$49.90 - $52.90
A white linen skater dress featuring a corset lace-up back and sweetheart neckline with bust tie.
$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.
$52.90
A white lace skater dress featuring a scoop neckline, ruffle trim, and adjustable spaghetti straps.
$32.90
A chic red sleeveless midi dress with ruched seams and a curve-hugging bodycon silhouette.
$24.97 $54.90 55% off
A floral ivory skater dress featuring a halter V-neckline and voluminous silhouette in poplin fabric.
$44.90
A yellow skater dress featuring eyelet lace embroidery and a stretchy smocked bodice.
$26.97 $59.90 55% off
A chic black satin maxi dress with a halter neckline and high front slit for bold elegance.
$19.97 $35.90 44% off
A strapless taupe midi dress with a tropical print and flared hem, perfect for vacations.
$59.90
An ivory A-line maxi dress featuring gauze fabric, sheer lace insets, and a faux leather belt.
$34.90
An eyelet knit mini dress in pink with a flirty bust tie and A-line silhouette.
$42.90
A navy blue paisley skater dress with a halter V-neckline and playful tie-back design.
$19.97 $35.90 44% off
A strapless tropical midi dress in dark marsala with a bodycon silhouette and side slit.
$49.90
A black woven mini dress with pleated A-line silhouette and spaghetti strap ties for casual outings.
$46.90
A charming floral babydoll mini dress in natural with a flowy ruffled silhouette and smocked bust.
$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.
$19.97 $44.90 56% off
A pink floral maxi dress with a form-hugging bodice and flowy hem, perfect for special occasions.
$49.90
A natural knit halter mini dress with a bodycon silhouette and unique texture for beach strolls.
$34.90
A strapless white floral mini dress with an A-line silhouette and eyelet fabric.
$22.97 $49.90 54% off
A light blue chiffon skater dress with polka dots, a V-neckline, and adjustable spaghetti straps.
$52.90
A strapless ivory chiffon skater dress with a ruffled silhouette and stretchy smocked bodice.
$49.90
An ivory floral skater dress with a corset bodice and flared hem, perfect for sunny occasions.
$49.90
A strapless ivory skater dress with a floral print and flirty ruffled hem.
$42.90
A brown strapless mini dress with a bodycon silhouette, cargo pockets, and cotton-blend fabric.
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The Marissa long satin dress brings elegance and sultriness to your formal night. The floor-length gown enhances your curves with a fitted bodice and flattering A-line silhouette while the high front slit provides movement. Fit & FeaturesStretch-satin fabric, non-see-through, double-lined bust, Sleeveless pleated cowl neckline, spaghetti straps, Slim-fit bodice, empire waistline, High front slit, floor-length hem, A-line silhouette, Runs true to size, Where to Wear:Prom, weddings, black-tie soirees, special date nights, and engagement parties. Free Shipping on All Orders Over $75. | Windsor Marissa Formal Satin Cowl Neck Dress in Green | Size: S | Satin Fabric
Shine bright and sparkle up the night in the gorgeous Leila mini dress. The dress boasts an alluring open back with a lace-up strappy design for a customized fit, and a short, curve-hugging silhouette. Shop Long Version: Kailani Formal Sequin Slit Mermaid DressFit & FeaturesSheer mesh fabric, full knit lining, moderate stretch, Sequin embroidery, scroll pattern, Sleeveless square neckline, adjustable spaghetti straps, Open back, lace-up strappy design, tie closure, High waist seam, lower back zipper, hook and eye closure, Mini-length hem, fitted bodycon silhouette, Runs true to size, Where to Wear:Prom, bachelorettes, birthdays, Vegas weekends, date nights Free Shipping on All Orders Over $75. | Windsor Leila Sequin Bodycon Mini Dress in Royal Blue | Size: L | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
Look and feel like a sultry senorita in this mesh mini dress perfect for an chic night on the town! It features a sleeveless cowl neckline, dual adjustable spaghetti straps with a tie-neck closure, and side and back ruched seams designed to flaunt your curves along the bodycon silhouette. Complete the look with hoop earrings. Fit & FeaturesSleeveless cowl neckline, Dual adjustable spaghetti straps, tie-neck closure, Side and back ruched seams, Back zipper and hook-eye closure, Bodycon silhouette, mini-length hem, Mesh fabric, brushed soft knit stretchy lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Senorita Mesh Strappy Mini Dress in Pink | Size: XS | Knit Fabric/Mesh Fabric/Mesh 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: XL | Knit Fabric
Show up and stun this formal season in the gorgeous Brynlee bodycon mini dress! She features a sleeveless square neckline, a built-in padded bust, halter spaghetti straps, an open back with a lace-up design for a customized fit, and a short, curve-hugging silhouette. The lined mesh fabric features all-over sequin embroidery in an intricate scroll pattern. Style the formal mini dress with clear heels for a night to remember. Fit & FeaturesSleeveless, square neckline, Built-in padded bust, no bra required, Halter spaghetti straps, back button closure, Open back, lace-up design, zipper closure, Bodycon silhouette, mini-length hem, Sequin scroll embroidery, mesh fabric, knit lining, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Brynlee Sequin Embroidered Bodycon Dress in Sage | Size: S | Knit Fabric/Mesh Fabric/Mesh Fabric
Every occasion is worth celebrating in this off-the-shoulder midi dress! The smooth and stretchy knit fabric includes a full-length knit lining for additional coverage. The off-the-shoulder neckline and short-sleeve cuffs add a touch of elegance, while the bodycon silhouette and flared midi-length hem accentuate your curves in all the right places. Complete the look with teardrop earrings and heels. Fit & FeaturesSmooth stretchy knit fabric with knit lining, Off-the-shoulder neckline, Short-sleeve cuffs, Bodycon fit, Flare hem, Style runs small, Free Shipping on All Orders Over $75. | Windsor Exceptional Off-The-Shoulder Flared Midi Dress in Black-2 | Size: XL | Knit Fabric
Bring the dazzling glamour to the party in this long sleeve rhinestone mesh mini dress! Designed with a stretchy sheer mesh fabric with a partial knit lining, the mini-length dress is accented with all-over rhinestone embellishments for a gorgeous and chic shine. The square neckline shapes the bodice, and the unlined long sleeves have slit accents and flare out for a trendy look. The bodycon silhouette will hug your gorgeous curves. Style this mini dress with rhinestone heels for all the more sparkle. Fit & FeaturesStretchy sheer mesh fabric, partial knit lining, Rhinestone embellishments, Square neckline, Long bell sleeves with slit detail, Back zipper, hook and eye closure, Bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Dazzling Glam Long Sleeve Rhinestone Mesh Mini Dress in Beige | Size: XL | Knit Fabric/Rhinestone/Mesh Fabric
A mini dress that brings the luxe sensation! The Keira faux pearl short dress is a stunning style with a strappy tie-back design and a bodycon silhouette that highlights your figure. Fit & FeaturesLightweight mesh fabric, stretchy knit lining, Faux pearl and bead embellishments, Sleeveless cowl neckline, Spaghetti straps, strappy tie-back design, open-back, Bodycon silhouette, mini-length hem, Runs true to size, Where to Wear:Prom, birthday parties, bachelorettes, Vegas weekends, rooftop cocktails Free Shipping on All Orders Over $75. | Windsor Keira Faux Pearl Strappy Open-Back Mini Dress in Pink | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
The first step is picking the right dress. You're going to be working it in this figure-hugging mini! Put your hair in a half-up-do and slip into some heels for a bomb AF look! The dress features a sleeveless cowl neckline, spaghetti straps that cross at the back, and an asymmetrical hem. Complete the outfit with sleek hoop earrings. Fit & FeaturesSleeveless drapey cowl neckline, Spaghetti straps, cross at back, Mini length, asymmetric hemline , Smooth knit fabric, metallic sheen , Form-hugging fit , Plenty of stretch , Runs true to size, Free Shipping on All Orders Over $75. | Windsor All The Right Moves Cowl Neck Mini Dress in Green | Size: S | Knit Fabric
Everyone will see you shining at the club in this glitter mini dress! It features an off-the-shoulder sweetheart neckline, sheer fitted ruched long sleeves, adjustable spaghetti straps, a ruched seam along the padded bust, a sheer bodice with trim, and side ruched seams that hug your curves on the bodycon silhouette. Complete the look with a clutch and heels. Fit & FeaturesOff-the-shoulder sweetheart neckline, Adjustable spaghetti straps, Sheer fitted ruched long sleeves, Ruched and padded bust, sheer bodice, trim, Side ruched seams, bodycon silhouette, mini-length hem, Glitter mesh fabric, sewn-in knit lining, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor See Me Shining Glitter Off-The-Shoulder Mini Dress in Navy Blue | Size: L | Knit Fabric/Mesh Fabric/Mesh Fabric
Casual Vacation Dresses
When it comes to planning a getaway, packing the right casual vacation dresses is basically the golden ticket to stress-free style. Whether you’re jet-setting to a tropical paradise, road-tripping with your ride-or-die crew, or just living for that “out of office” energy, these dresses are your go-to for effortless vibes. Think easy, breezy silhouettes that let you move, groove, and snap those Insta-worthy pics without a second thought. The Windsor girl knows that comfort doesn’t mean sacrificing style—she wants to look put-together while feeling like she could dance barefoot on the sand or twirl through a local market. That’s why casual vacation dresses are all about flowy fabrics, playful details, and those little touches (like a flirty tie-back or a cheeky cutout) that turn a simple dress into a full-on main character moment. If you’re gifting, trust that these dresses are a foolproof pick for the friend who’s always planning the next adventure or the sister who loves a good “pack light, look cute” challenge. And if you’re treating yourself, you already know you deserve to be the best-dressed wherever you land.
Choosing the perfect casual vacation dress is all about matching your mood and your itinerary. Maybe you’re after a laid-back look for exploring hidden gems and sipping iced lattes, or you want something a little extra for sunset dinners and spontaneous nights out. Windsor casual dresses have your back with options that nail that sweet spot between chill and chic. Picture yourself in an exceptional off-the-shoulder flared midi dress, catching the breeze as you stroll along the boardwalk, or slipping into something soft and strappy for a rooftop brunch with your besties. The best part? These dresses play well with your whole wardrobe—throw on a denim jacket, layer up the jewelry, or go barefoot and carefree. With Windsor vacation dresses, versatility is the name of the game, making them a no-brainer for travel, gifting, or just upgrading your everyday rotation.
For the girls who live for a little spontaneity, casual vacation dresses are the ultimate style hack. They’re the answer to “What should I wear?” when you’re running late for a ferry, hopping on a scooter, or saying yes to last-minute plans. And let’s be real: nothing feels more iconic than tossing on a cute dress that makes you feel unstoppable, whether you’re headed to a poolside hang or a dreamy dinner under the stars. These dresses are designed for real life—wrinkle-friendly, suitcase-approved, and ready for whatever adventure you throw their way. If you’re looking to expand your vacation wardrobe or just want to browse more effortlessly chic options, check out our curated collection of Cute Vacation Dresses for even more inspo. No matter where you’re headed or who you’re gifting, Windsor’s casual vacation dresses are your ticket to looking and feeling like the main event—every single day of your getaway.