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!
$32.90
A chic denim strapless A-line mini dress with pleated bust and stretchy knit fabric.
$36.90
An elegant sage off-the-shoulder midi dress with a flared hem and smooth knit fabric.
$32.90
A pink mini A-line dress with a flirty bust tie and stretchy knit fabric.
$64.90
A white woven skater dress featuring a lace-up back, ruched bust, and tiered A-line silhouette.
$46.90
A bronze knit maxi dress featuring a trendy lace-up back and flattering bodycon silhouette.
$39.90
A brown knit midi dress with long sleeves, off-the-shoulder neckline, and ruched bodycon fit.
$34.90
A black abstract floral mini dress featuring a cowl halter neckline and ruffled slit design.
$32.90
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.
$59.90
A white woven maxi dress featuring a floral print, open tie back, and ruffled silhouette.
$34.90
A strapless red mini dress with an abstract floral print, side ruching, and asymmetric hem.
$46.90
A navy blue strapless mini skater dress in stretchy poplin with a ruched bodice and pleated hem.
$32.90
A chic red sleeveless midi dress with ruched seams and a curve-hugging bodycon silhouette.
$44.90
A black one-shoulder tropical maxi dress with a ruffled slit and metal-accented strap.
$46.90
A pink knit maxi dress featuring a halter neckline, bodycon fit, and an alluring lace-up back.
$46.90
An ivory striped midi dress with cutouts, adjustable straps, and dual side slits for casual elegance.
$32.90
A breezy white eyelet knit skater dress featuring a square neckline and double-layered flared skirt.
$34.90
An orange abstract print mini dress featuring sheer mesh, halter neckline, side cutouts, and open back.
$9.97 $42.90 77% off
A slate A-line mini dress with a V-neckline and ruffled hem in soft knit fabric.
$38.90
A tropical print maxi dress in black with sheer mesh fabric and a high side slit.
$34.90
A chic brown strapless maxi dress with a high slit and flattering bodycon silhouette.
$35.90
An olive green tropical print mini dress featuring a V-neckline, twisted bust, and strappy tie-back.
$19.97 $39.90 50% off
A khaki woven midi dress with a smocked bodice, square neckline, and ruffled A-line silhouette.
$46.90
An olive green gauze skater dress featuring flowy sleeves, V-necklines, and a chic cutout bodice.
$39.90
An ivory satin mini dress featuring a tropical floral print, strapless neckline, and flowy A-line silhouette.
$44.90
A taupe paisley skater dress featuring a halter V-neck and stretchy smocked bodice.
$44.90
A natural ribbed knit midi dress featuring a bold cutout bodice, side slit, and bodycon silhouette.
$42.90
A black tropical floral maxi dress featuring a square halter neckline, criss-cross back, and high side slit.
$44.90
A rust-colored one-shoulder maxi dress with a tropical print, side cutout, and high slit.
$32.90
A natural crochet knit mini dress featuring a strapless neckline, side slit, and bodycon silhouette.
$59.90
An ivory A-line maxi dress with gauze fabric, sheer lace insets, and a faux leather belt.
$22.97 $49.90 54% off
A black woven mini dress with pleated A-line silhouette and spaghetti strap ties for casual outings.
$19.97 $44.90 56% off
A vibrant orange geometric print midi dress in smooth knit fabric with a halter neckline and open back.
$49.90
A brown mesh maxi dress featuring a bold floral print, drapey cowl halter neckline, and curve-hugging fit.
$46.90
A charming floral babydoll mini dress in natural with a flowy ruffled silhouette and smocked bust.
$46.90
An abstract red knit maxi dress featuring a cowl neckline, hoop trims, strappy back, and high side slit.
$42.90
A navy blue paisley skater dress with a halter V-neckline and playful tie-back design.
$44.90
A mint crochet mini dress featuring a beaded halter neckline, cutout front, and bodycon silhouette.
$46.90
A sage green mini dress featuring a halter neckline, ruffled skater silhouette, and airy woven fabric.
$54.90
A breezy natural linen-blend maxi dress featuring a sleek halter neckline, open tie back, and high side slit.
$38.90
A sultry orange knit midi dress featuring a one-shoulder neckline, front cutouts, and gold O-ring accents.
$44.90
A sultry black floral maxi dress with a V-neckline and form-hugging silhouette, perfect for vacations.
$26.90
A taupe plaid mini dress with a V-neckline, spaghetti straps, and a bodycon silhouette.
$46.90
A natural knit maxi dress featuring a bold tropical leaf print, one-shoulder cutout, and gold hardware.
$42.90
A taupe tropical print maxi dress featuring mesh fabric, a one-shoulder neckline, and chic O-ring detail.
$42.90
A light blue gingham skater dress featuring a smocked waist, sweetheart neckline, and adjustable straps.
$44.90
A black tropical print maxi dress featuring a cutout bodice, sweetheart neckline, and high side slit.
$69.90
A natural gauze midi dress featuring a strapless smocked bodice and cascading ruffled silhouette.
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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: XL | 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 Red | Size: M | 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 Natural | Size: XS | 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: 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
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 Light Blue-2 | Size: XS | Knit Fabric/Mesh Fabric/Mesh 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: XL | 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 Wine | Size: S | Knit Fabric/Mesh Fabric/Mesh Fabric
Both sexy and demure, the Kristen party dress wows from every angle! Perfect for bachelorette weekends, themed soirees, and formal birthdays! She features a sleeveless sweetheart neckline with a padded bust, cowl draping, adjustable spaghetti straps, and side ruched seams that hug your curves along her short bodycon silhouette. The formal party dress is composed of a faux pearl embellished mesh fabric with a stretchy knit lining. Complete the look in statement block heels. Fit & FeaturesSleeveless sweetheart neckline, Padded bust, cowl draping, Adjustable spaghetti straps, Side ruched seams, bodycon silhouette, Mini-length hem, Faux pearl embellishments, mesh fabric, stretch knit lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Kristen Faux Pearl Mini Party Dress in White | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
Casual Vacation Dresses
Let’s be real—packing for that getaway shouldn’t feel like a game of Tetris. Whether you’re jetting off to a dreamy beach, plotting a road trip with your ride-or-die crew, or just living your best life at a backyard brunch, casual vacation dresses are your ultimate plus-one. These are the dresses that don’t just sit pretty in your suitcase—they jump out, ready to make memories and rack up compliments. Think flowy silhouettes that let you twirl through cobblestone streets, breezy fabrics that keep you cool when the group chat is blowing up with brunch plans, and details that go from “just checking out the sights” to “dancing all night” without missing a beat. The best part? A windsor casual dress is made for the girl who wants to look effortlessly put-together with zero stress—because who has time to worry about outfit changes when the world is calling?
Choosing the right casual vacation dress is all about knowing your vibe and owning it. If you’re the spontaneous type who loves to say yes to every adventure, opt for styles that are easy to throw on and go—think soft jersey knits, playful ruffles, or a flirty wrap that moves with you. Maybe you’re shopping for yourself, or maybe you’re picking out a gift for your bestie who’s always planning the next group trip (and let’s be honest, she deserves a little extra love for keeping everyone’s flights organized). Either way, these dresses are a game-changer for anyone who wants to pack light but still serve looks. They’re perfect for those Insta-worthy moments—picture yourself sipping iced coffee at a sidewalk café, exploring hidden gems, or just catching golden hour with your crew. And because windsor casual dresses are designed to mix and match, you can easily style them up or down with a quick change of shoes or a statement accessory. That’s the magic: one dress, endless possibilities, and a suitcase that actually zips shut.
No matter where your wanderlust takes you, the right casual vacation dress is all about feeling confident, comfortable, and totally yourself. These aren’t just dresses—they’re your ticket to unforgettable memories, spontaneous adventures, and the kind of carefree fun that only happens when you’re surrounded by your favorite people. Whether you’re shopping for a last-minute getaway or building your dream capsule wardrobe, you’ll find that a windsor casual dress is the hero piece you’ll reach for again and again. Ready to level up your vacay style? Check out our curated collection of Casual Vacation Outfits for even more inspo, and get ready to make every day feel like a getaway.