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!
$42.90
A strapless ivory lace skater dress with ruffled hem, perfect for a night of dancing.
$46.90
A brown woven midi dress with a ditsy floral pattern, corset bodice, and high front slit.
$36.90
A denim satin mini dress with a ruched wrap silhouette and spaghetti straps for a chic look.
$32.90
A sultry pink mesh mini dress with adjustable straps and ruched seams for a chic night out.
$32.90
A strapless pink A-line mini dress with pleated bust, perfect for cocktail or formal occasions.
$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.
$19.97 $34.90 43% off
A sultry fuchsia mini dress with ruched detailing and a curve-hugging, stretchy knit silhouette.
$37.90
A denim satin strapless mini dress with a pleated bust and flattering bodycon silhouette.
$46.90
A vibrant yellow skater dress with a ruffled design, halter tie-back, and smocked high waist.
$44.90
A red floral print mesh maxi dress with a sleeveless sweetheart neckline and bodycon silhouette.
$52.90
A strapless white mini dress with sequin bows and a satin lace-up back on mesh fabric.
$64.90
A white woven skater dress featuring a lace-up back, ruched bust, and tiered A-line silhouette.
$46.90
A denim skater mini dress with a sweetheart neckline and chiffon lace trim for festival flair.
$32.90
A pink mini A-line dress with a V-neck and flirty bust tie, perfect for special occasions.
$49.90
A sleeveless black 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.
$42.90
A chic ivory mesh bodycon dress with floral print, adjustable straps, and a stylish side slit.
$59.90
A light blue woven midi dress featuring a corset bodice and charming lace-up back detail.
$48.90
A breezy white eyelet knit mini skater dress with a flirty tie-back and ruffled hem.
$42.90
A vibrant yellow halter bodycon mini dress in stretchy knit fabric, perfect for any occasion.
$46.90
A sultry brown maxi dress featuring a twist plunge V-neckline, cutout bodice, and ruffled slit.
$39.90
A dainty white mini dress featuring sheer floral lace, ruffled puff sleeves, and a flattering empire waist.
$19.97 $42.90 53% off
A mauve floral mesh midi dress with a bodycon silhouette and asymmetrical ruffled hem.
$23.97 $52.90 55% off
A black floral mesh midi dress with a sweetheart neckline, ruching, and a flirty side slit.
$44.90
A pink floral mesh corset mini dress with a sweetheart neckline and adjustable spaghetti straps.
$34.90
A black abstract floral mini dress featuring 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.
$69.90
A charming ivory floral skater dress featuring a lace-up corset bodice and sheer lace trims.
$22.97 $49.90 54% off
A pink floral print mesh maxi dress with a fitted silhouette and adjustable spaghetti straps.
$35.90
A natural-colored sleeveless wrap mini dress in stretchy knit fabric with a form-hugging fit.
$35.90
A pink sleeveless bodycon midi dress with a square neckline and stretchy knit fabric.
$35.90
A red-brown bodycon mini dress with a one-shoulder neckline and soft hacci knit fabric.
$35.90
An ivory floral eyelet mini dress with a V-neckline and adjustable spaghetti straps.
$52.90
A pink lace mini dress with butterfly embroidery, tie-back design, and ruffled adjustable straps.
$20.97 $46.90 55% off
A white strapless skater dress with a ruched bodice and playful pleated hem.
$42.90
A sultry pink strapless mesh mini dress with ruffled trim and bodycon silhouette.
$36.90
A chic black mini dress with a pleated cowl neckline and flowy A-line silhouette.
$59.90
A white woven maxi dress featuring a floral print, open tie back, and ruffled silhouette.
$19.97 $42.90 53% off
A pink sleeveless skater dress with a ruffled silhouette and square neckline, perfect for brunch.
$19.97 $32.90 39% 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 casual elegance.
$36.90
A green knit mini dress featuring a halter neckline, pleated bust, and open back cutout.
$44.90
A black one-shoulder tropical maxi dress with a ruffled slit and metal-accented strap.
$19.97 $34.90 43% off
A taupe mesh mini dress with abstract print, O-ring accents, and an asymmetric waist cutout.
$59.90
A charming red gingham skater dress featuring an open back, ruffled hem, and sweetheart neckline.
$19.97 $42.90 53% off
A sultry red mini dress with a plunge-wired halter neckline and ruched side seams.
$36.90
A lavender ribbed knit mini dress with a scoop neckline and flattering skater 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: 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 Red | Size: M | 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
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
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
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
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
Cute Vacation Dresses
Let’s be real, a getaway is basically just an excuse to show off your cutest looks—and cute vacation dresses are the ultimate main character move. Whether you’re jetting off to a tropical paradise, city-hopping with your ride-or-die crew, or just living your best life on a spontaneous road trip, the right dress is your ticket to feeling unstoppable. Think of packing as curating your own highlight reel: you want pieces that work from sunrise mimosa runs to late-night dance floors, with zero outfit changes required. That’s where breezy, flirty styles like cute sundresses for vacation come in clutch. Picture yourself twirling through a cobblestone street, the hem of your dress catching the golden hour light, or lounging poolside in a lace vacation dress that’s equal parts dreamy and daring. These aren’t just clothes—they’re confidence boosters, icebreakers, and the kind of instant outfit magic that turns a regular day into a core memory.
Choosing the right Windsor vacation dresses is all about balancing vibe and versatility. Go for lightweight fabrics that keep you cool when things heat up (and let’s be honest, you’re always bringing the heat), and silhouettes that let you move, groove, and pose for those impromptu photo ops. Flowy maxis, playful minis, and anything with a pop of color or a cheeky cut-out are all fair game. If you’re shopping for your BFF, your sister, or that friend who’s always planning the next adventure, these styles make the perfect gift—because who wouldn’t want to unwrap a little slice of vacation energy? And don’t sleep on the power of spring vacation dresses for those last-minute getaways or destination celebrations. They’re the kind of pieces you’ll reach for again and again, whether you’re brunching with the squad or making your own fun wherever you land. The best part? You don’t have to break the bank to look like a million bucks—affordable, on-trend, and ready for anything, Windsor dresses have your back.
Let’s be honest, every trip deserves its own fashion moment. That’s why it’s smart to build your suitcase around a few show-stopping, easy-to-style pieces. Think dresses that can go from beach cover-up to rooftop cocktails with just a switch of shoes, or a lace vacation dress that doubles as the ultimate date night ‘fit. Don’t forget to check out Casual Vacation Dresses for even more inspo—because your dream vacay wardrobe is just a click away. Whether you’re packing for a bucket-list destination or just want to channel those carefree getaway vibes at home, these dresses are your passport to feeling fearless, fabulous, and totally unforgettable. So go ahead, make every destination your runway and every moment your best one yet.