Cute Vacation Dresses
Pack your bags, babe, because the ultimate getaway just got a whole lot cuter with our collection of cute vacation dresses! Whether you're jet-setting to a tropical paradise or planning a chic city escape, these dresses are your passport to turning heads and stealing hearts. Designed for sunshine-filled days and dreamy sunset strolls, each piece is ready to make you feel like the main character in your own travel story. So slip into something fabulous and let those vacay vibes flow—adventure awaits, and you're dressed to impress!
$46.90
A bronze knit maxi dress featuring a trendy lace-up back and flattering bodycon silhouette.
$36.90
A denim satin mini dress with a ruched wrap silhouette and spaghetti straps for a chic look.
$32.90
A strapless pink A-line mini dress with pleated bust, perfect for cocktail or formal occasions.
$32.90
A sultry pink mesh mini dress with adjustable straps and ruched seams for a chic night out.
$36.90
An elegant pink off-the-shoulder midi dress with a stretchy knit fabric and flared hem.
$59.90
A white mini dress with iridescent sequins, sheer velvet fabric, and adjustable spaghetti straps.
$36.90
A pink ribbed knit skater dress with an off-the-shoulder neckline and long fitted sleeves.
$40.90
A black glitter mini dress with a halter cowl neckline and tie-back spaghetti straps.
$37.90
A denim satin strapless mini dress with a pleated bust and flattering bodycon silhouette.
$68.90
A chic mauve skater dress featuring floral jacquard satin, a corset bodice, and lace-up back.
$32.90
A pink mini A-line dress with a V-neck and flirty bust tie, perfect for special occasions.
$64.90
A white woven skater dress featuring a lace-up back, ruched bust, and tiered A-line silhouette.
$52.90
A strapless white mini dress with sequin bows and a satin lace-up back on mesh fabric.
$49.90
An enchanting sage skater dress featuring sheer lace, a V-neckline, and adjustable spaghetti straps.
$38.90
A white eyelet knit skater dress featuring a sleeveless square neckline and adjustable spaghetti straps.
$34.90
A black abstract floral mini dress featuring a cowl halter neckline and ruffled slit design.
$42.90
A sultry pink strapless mesh mini dress with ruffled trim and bodycon silhouette.
$59.90
A light blue woven midi dress featuring a corset bodice and charming lace-up back detail.
$26.97 $59.90 55% off
A natural floral chiffon skater dress with a strapless lace-trimmed sweetheart neckline and charming bow.
$48.90
A breezy white eyelet knit mini skater dress with a flirty tie-back and ruffled hem.
$35.90
A pink sleeveless bodycon midi dress with a square neckline and stretchy knit fabric.
$59.90
A white woven maxi dress featuring a floral print, open tie back, and ruffled silhouette.
$36.90
A lavender ribbed knit mini dress with a scoop neckline and flattering skater silhouette.
$44.90
A white floral skater dress with a strappy tie-back and ruffled mini-length hem.
$42.90
A strapless ivory lace skater dress with ruffled hem, perfect for a night of dancing.
$44.90
A charming ivory pointelle knit skater mini dress with a scoop neckline and wide shoulder straps.
$34.90
A strapless red mini dress with an abstract floral print, side ruching, and asymmetric hem.
$35.90
A chic red-brown bodycon mini dress with a one-shoulder neckline and soft hacci knit fabric.
$36.90
A chic black mini dress with a pleated cowl neckline and flowy A-line 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.
$9.97 $32.90 70% off
A strapless white eyelet lace mini dress perfect for bridal showers or brunch.
$46.90
An ivory striped midi dress with cutouts, adjustable straps, and dual side slits for a chic look.
$59.90
A charming red gingham skater dress featuring an open back, ruffled hem, and sweetheart neckline.
$36.90
A green knit mini dress featuring a halter neckline, pleated bust, and open back cutout.
$39.90
A sheer white crochet knit cover-up dress featuring a plunge neckline, hoop insert, and long flared sleeves.
$49.90
A strapless denim mini dress with a skater silhouette and pleated hem for a flirty vibe.
$34.90
An orange abstract print mini dress featuring sheer mesh, halter neckline, side cutouts, and open back.
$29.90
A strapless brown lace mini dress with a flared hanky hem for standout occasions.
$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.
$49.90
A yellow eyelet skater dress featuring a V-neckline, adjustable spaghetti straps, and a tie-back design.
$19.97 $39.90 50% off
A khaki woven midi dress with a smocked bodice, square neckline, and ruffled A-line silhouette.
$39.90
An ivory lace ruffle mini dress with a form-hugging fit and shark bite hem.
$39.90
An ivory satin mini dress featuring a tropical floral print, strapless neckline, and flowy A-line silhouette.
$39.90
An eyelet lace mini dress in white with ruffled straps and a ruched sweetheart neckline.
$35.90
An olive green tropical print mini dress featuring a V-neckline, twisted bust, and strappy tie-back.
$39.90
A brown mesh mini dress featuring a strapless neckline, side cutout, and ruffle-trim slit.
Now Trending
Get all wrapped up in this stylish sleek satin mini dress. Dance the night away at that upcoming wedding or celebrate a girl's night in this statement dress that will have all eyes on you. The dress features a sleeveless square neckline, spaghetti straps, and a ruched wrap silhouette that hugs curves in all the right places. The mini-length dress is composed of a satin-like fabric that offers a moderate stretch. Complete your look with rhinestone earrings and strappy heels. Fit & FeaturesSleeveless square neckline, spaghetti straps, Strapless bra recommended, Ruched wrap-front detail , Mini-length bodycon silhouette , Satin-like fabric, sheen finish, Form-hugging fit, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Wrapped In Stylish Satin Mini Dress in Denim | Size: XS | Rhinestone/Satin Fabric
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 Navy Blue | Size: L | Knit Fabric
The Lucy mini party dress is sleek and simple from the front and stunning from the back. Turn heads as you stun from the back with a flirty big bow tie with a dramatic train that glides against the floor! Fit & FeaturesTaffeta structured woven-lined fabric, slight stretch, Strapless, square neckline, non-slip grip, Hidden side zipper, hook and eye closure, Front and back pleating and ruching, Form-hugging, mini-length hem, Detachable back bow with train, Runs true to size, Where to Wear:Homecoming, weddings, brides, bachelorettes, big birthday events, fancy date nights, gorgeous dinner parties, cocktail soirees, rehearsal dinners, engagement photoshoots and parties Free Shipping on All Orders Over $75. | Windsor Lucy Taffeta Bow Mini Party Dress in Black | Size: XL
Shine on in a sequin dress that brings the glitz and glam. Kathy features a plunging sleeveless V-neckline, iridescent sequins embroidered throughout, adjustable spaghetti straps for a customized fit, and a mini-length hem with a bodycon silhouette that will hug your curves. The sheer velvet fabric includes a full knit lining and offers a moderate stretch. Complete your A-list-worthy look with clear heels and rhinestone hoops. Fit & FeaturesSleeveless V-neckline, adjustable spaghetti straps, Back zipper, hook and eye closure, Mini-length hem, bodycon silhouette, Iridescent sequin embroidery, Sheer velvet fabric, full knit lining, moderate stretch, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Kathy Iridescent Sequin Mini Dress in White | Size: S | Knit Fabric/Rhinestone/Velvet 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 Sage | Size: M | Knit Fabric/Satin Fabric
Make yourself known in this satin mini dress as you step into the club or party! The short dress is designed with a strapless neckline with non-slip grip lining, a pleated bust and side seam, a flattering bodycon silhouette, and a mini-length hem. Style the satin dress with rhinestone heels for a charming sparkle! Fit & FeaturesStrapless neckline, non-slip grip lining, Pleated bust and side seam, Bodycon silhouette, Mini-length hem, Silky satin fabric, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Make It Known Satin Strapless Pleat Mini Dress in Denim | Size: S | Rhinestone/Satin Fabric
Dazzle from every angle in the sleek and stunning Marcy glitter mini party dress! Turn heads at weddings, school dances, and formal cocktail parties. She features a strapless, square neckline with non-slip grip lining, a hidden side zipper closure, and front and back pleat and ruching that creates the illusion of an hourglass figure. She stuns from the back with her flirty big bow tie with a dramatic train that glides against the floor. The formal dress is composed of a glitter woven fabric with a sewn-in knit lining and minimal stretch. Complete your dressy look in metallic heels and jewelry! Fit & FeaturesStrapless square neckline, non-slip grip lining, Strapless or sticky bra recommended, Hidden side zipper, hook and eye closure, Front and back pleat/ruching, bodycon fit, mini-length hem, Detachable back bow with train, Glitter woven fabric, sewn-in knit lining, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Marcy Glitter Bow Mini Party Dress in Light Blue | Size: L | Knit Fabric/Woven Fabric
Radiate major glam princess energy when you show up in this gorgeous sequin mini dress! It features a sleeveless square neckline, spaghetti straps, an alluring open back with a lace-up strappy design for a customized fit, a mini-length hem, and a form-hugging silhouette. The lined mesh fabric features iridescent sequin embroidery in an intricate scroll pattern that will catch the light beautifully. Complete your regal look with a matching rhinestone jewelry set. Fit & FeaturesSleeveless square neckline, spaghetti straps, Open back, lace-up strappy design, tie closure, Lower back zipper, hook and eye closure, Mini-length hem, form-hugging fit, Iridescent sequin embroidery, scroll pattern, Sheer mesh fabric, full knit lining, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Glam Princess Lace-Up Sequin Mini Dress in Pink | Size: XS | Knit Fabric/Rhinestone/Mesh 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
The style win is yours for the taking babe! Show everyone how it's done in this mesh mini dress perfect for dinner and drinks. It features a sleeveless sweetheart neckline, tank shoulder straps, a ruched lightly padded bust, and side ruched seams to accentuate your curves along the bodycon silhouette. The lined mesh fabric has a moderate stretch. Style this mini-length dress with a glitter clutch and heels. Fit & FeaturesSleeveless sweetheart neckline, tank shoulder straps, Lightly padded ruched bust, Back zipper and hook-eye closure, Side ruched seams, bodycon silhouette, Mini-length hem, Lined mesh fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Winning Style Mesh Ruched Mini Dress in Red | Size: XS | Mesh Fabric/Mesh Fabric
Cute Vacation Dresses
When it comes to curating the ultimate travel wardrobe, cute vacation dresses are the secret weapon every Windsor girl needs in her suitcase. Imagine breezing through sun-drenched boardwalks, hopping from dreamy beach brunches to rooftop soirées, or twirling under city lights in a dress that practically screams “main character energy.” Whether you’re planning a spontaneous girls’ getaway, a romantic escape, or just want to look fire for those endless photo ops, the right vacation dress is more than just an outfit—it’s your ticket to feeling unstoppable wherever the adventure takes you. These dresses are all about easy, throw-on-and-go vibes that still serve major style, letting you pack light without ever sacrificing your look. Think flowy silhouettes that catch every breeze, playful prints that pop against golden skin, and details like smocked bodices, open backs, or flirty cutouts that are just begging for a little trouble. And because we know not every Windsor girl is about the frills, you’ll find plenty of not girly vacation dress options—think sleek slip dresses, edgy shirt dresses, or minimalist wrap styles that deliver confidence with a side of sass.
Shopping for dresses for vacation is all about embracing your inner jetsetter and making every day feel like a new adventure. Maybe you’re the friend who plans every itinerary down to the minute, or maybe you’re the spontaneous soul who says “yes” to every last-minute invite—either way, your dress should be as ready for anything as you are. Lightweight fabrics are a must for those days when the sun is relentless and the only thing on your agenda is soaking up good vibes. Look for easy-care materials that resist wrinkles, so you can toss your dress in your bag and still look put together when you land. If you’re gifting, vacation dresses are a killer pick for birthdays, bachelorette parties, or just because your bestie deserves to feel like a goddess on her next trip. They’re the ultimate “I saw this and thought of you” present, perfect for anyone who lives for travel, adventure, and turning every sidewalk into a runway. And let’s be real: there’s nothing like that first twirl in a new dress to set the tone for an unforgettable trip.
No matter your destination or vibe, Windsor vacation dresses are designed to keep up with your wildest plans. From sunrise coffee runs to moonlit dance floors, these styles are made for making memories—and looking flawless while you do it. If you’re all about that effortless, lived-in glam, don’t miss our collection of Casual Vacation Dresses for even more inspo on how to keep things cute and comfy from takeoff to touchdown. Whether you’re hunting for spring vacation dresses to kick off your next escape or just want to refresh your travel lineup with pieces that work just as well at home as they do abroad, Windsor has your back. Pack your bags, cue the playlist, and get ready to make every moment a little more iconic—because with the right dress, you’re not just on vacation, you’re on a Windsor vacation.