Women's Vacation Dresses
Ready to make every getaway a main character moment? Women’s vacation dresses are here to turn your travel daydreams into reality—no passport drama required. From poolside hangs to rooftop dinners, these dresses are all about easy-breezy vibes and unforgettable entrances. Whether you’re jet-setting or just manifesting that next trip, your suitcase (and your Insta feed) deserve a lineup that’s as bold and spontaneous as you are. Get ready to pack the attitude—these women’s vacation dresses are bringing the heat.
$42.90
A green knit midi dress featuring a strapless sweetheart neckline, pleated overlay, and back slit.
$36.90
An elegant sage off-the-shoulder midi dress with a bodycon fit and flared hem.
$38.90
A white sleeveless ribbed knit midi dress featuring a V-neckline and chic high front slit.
$40.90
A black glitter mini dress with a halter cowl neckline and tie-back spaghetti straps.
$37.90
A pink satin strapless mini dress with pleated details and a flattering bodycon silhouette.
$46.90
A brown woven midi dress with a ditsy floral pattern, corset bodice, and high front slit.
$44.90
A red mesh maxi dress with a floral print, sweetheart neckline, and bodycon silhouette.
$54.90
An ivory floral satin dress with a lace-up back and flirty A-line silhouette.
$49.90
An ivory mesh midi dress with a dainty floral print, ruched seams, and a draped cowl neckline.
$44.90
A gold metallic knit maxi dress featuring a plunge cowl halter neckline and adjustable strappy open back.
$49.90
A lavender glitter skater dress with sheer peasant sleeves and a fit and flare silhouette.
$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.
$39.90
A sheer white crochet knit cover-up dress with long sleeves, plunge neckline, and chic hoop insert.
$19.97 $34.90 43% off
A blue strapless bodycon mini dress in smooth knit fabric with a bold large floral print.
$44.90
A black floral maxi dress featuring sheer mesh, a lace-up strappy back, and a form-hugging silhouette.
$39.90
A brown mesh mini dress featuring a strapless neckline, side cutout, and ruffle-trim slit.
$39.90
A mauve floral off-shoulder bodycon dress in stretchy knit fabric with soft ruching and flared hem.
$54.90
A sleeveless denim maxi dress featuring a flowy ruffled silhouette and lightweight woven fabric.
$38.90
A vibrant pink mini dress featuring a leopard snake print, mesh fabric, side cutout, and ruffled slit.
$39.90
A white eyelet lace mini dress with ruffled straps and a ruched sweetheart neckline.
$9.97 $52.90 81% off
A light blue strapless mini dress featuring eyelet woven fabric, a smocked bodice, and ruffled hem.
$36.90
An abstract rust mesh mini dress featuring a cowl halter neckline, cutout bodice, and ruffled slit.
$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.
$38.90
A pink floral mesh midi dress featuring a strapless neckline and curve-hugging fit for elegant occasions.
$19.97 $44.90 56% off
A floral chiffon skater dress in ivory with a strapless smocked bodice and ruffled silhouette.
$49.90
A brown mesh maxi dress featuring a bold floral print, cowl halter neckline, and curve-hugging fit.
$9.97 $37.90 74% off
An ivory floral bodycon mini dress featuring a strapless neckline and flirty ruffled hem.
$20.97 $46.90 55% off
An olive green gauze skater dress featuring V-neck cutouts, flowy sleeves, and a breezy silhouette.
$44.90
A white floral chiffon skater dress featuring charming ruffles, a strapless neckline, and a smocked bodice.
$19.97 $39.90 50% off
A natural paisley maxi dress featuring mesh fabric, a bodycon silhouette, and a high side slit.
$44.90
A girly green gingham mini dress with smocked cotton fabric, ruffled details, and adjustable straps.
$49.90
A brown floral mesh maxi dress featuring a curve-hugging fit and flirty strappy open back.
$39.90
An ivory lace skater dress with an off-the-shoulder neckline and sheer long fitted sleeves.
$19.97 $34.90 43% off
A yellow striped knit mini dress featuring a twisted strapless neckline and flattering bodycon silhouette.
$9.97 $49.90 80% off
A floral ivory mini dress featuring a corset bodice, lace-up back, and adjustable spaghetti straps.
$64.90
A blue floral bodycon mini dress featuring ruffled hem, square neckline, and stretch woven fabric.
$26.90
A taupe plaid mini dress with a V-neckline, spaghetti straps, and a bodycon silhouette.
$32.90
An ivory off-the-shoulder mini dress in striped ribbed knit offers cozy flair and stretch.
$19.97 $34.90 43% off
A light blue strapless maxi dress featuring bold floral mesh, stretchy knit lining, and a curve-hugging fit.
$44.90
A strapless burgundy mesh maxi dress featuring a bold floral print and a high side slit.
$39.90
A strapless brown mini dress featuring an abstract print, cutout back, and ruffled hem.
$59.90
A sage satin formal dress featuring a sleeveless square neckline, high-cut slit, and floor-length hem.
$32.90
A lime yellow mesh mini dress with a cowl neckline and adjustable spaghetti straps for a chic night.
$36.90
A brown abstract print mini dress featuring a cowl halter neckline, hoop accents, and stretchy knit fabric.
$46.90
A chic black bodycon midi dress with a square neckline and stretchy double-lined knit fabric.
$89.90
A black glitter knit bodycon dress with a cutout underbust and adjustable spaghetti straps.
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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: L | Knit Fabric/Mesh Fabric/Mesh 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 White | Size: XS
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
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 White | Size: L | Knit Fabric/Satin Fabric
Express your devotion to romance in the Lena mesh mini dress perfect for modern brides, birthday girls, or graduates! The strapless cowl neckline adds a touch of elegance, while the bodycon fit accentuates your figure. Fit & FeaturesBeaded mesh fabric, stretchy knit lining, Strapless cowl neckline, Back zipper and hook-eye closure, Bodycon fit, mini-length hem, Runs true to size, Where to Wear:Prom, date nights, bachelorettes, girl's night out, birthdays Free Shipping on All Orders Over $75. | Windsor Lena Strapless Bodycon Beaded Mesh Mini Dress in White | Size: M | 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: M | Knit Fabric
Bling on the sultry glamour with the sparkling details of the stunning Catalina formal mini dress with a bodycon silhouette that will flaunt your gorgeous figure! Fit & FeaturesSheer mesh fabric, full-length knit lining, plenty of stretch, Mini iridescent rhinestones, faux pearl embellishments, Sleeveless cowl neckline, Adjustable spaghetti straps, Mini-length hem, bodycon silhouette, Runs true to size, Where to Wear:Prom, bachelorettes, birthdays, girl's night out, date nights Free Shipping on All Orders Over $75. | Windsor Catalina Rhinestone And Pearl Formal Mini Dress in White | Size: M | Knit Fabric/Rhinestone/Mesh Fabric
Show off a flawless allure in this figure-flaunting mini dress! Designed with a sleek knit fabric with a fab sheen, this mini-length dress offers plenty of stretch so you can dance all night. The sleeveless bodice is shaped with a pleated cowl neckline for a chic draped effect and spaghetti straps. The pleating across the bodycon silhouette will accentuate your stunning curves. Style with metallic heels for a club night out.Fit & FeaturesStretchy sleek knit fabric, Sleeveless pleated cowl neckline, Spaghetti straps, Pleating, Bodycon fit, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flawless Allure Cowl Neck Bodycon Mini Dress in Pink | Size: L | Knit Fabric
Keep it sophisticated with a satin mini dress that radiates luxe. The dress features a sleeveless square neckline, detachable rhinestone embellished spaghetti straps, ruched side and back seams, and a form-hugging silhouette and mini-length hem. Complete look with rhinestone heels and a satin clutch. Fit & FeaturesSleeveless square neckline, Detachable rhinestone spaghetti straps, Ruched side and back seams, Form-hugging silhouette, Mini-length hem, Lined sleek satin fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Stunning Sophistication Rhinestone Mini Dress in Wine | Size: M | Rhinestone/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 Pink | Size: L | Rhinestone/Satin Fabric
Women's Vacation Dresses
When it comes to planning your next getaway, there’s one thing you can’t leave off your packing list: the perfect vacation dress. Picture this—you, sun-kissed and glowing, sipping something sweet as the breeze plays with your hem, all eyes on you and your effortlessly flawless style. That’s the magic of vacation dresses for women. These aren’t just outfits; they’re your ticket to main character energy, whether you’re wandering cobblestone streets, dancing under neon lights, or catching golden hour on a rooftop. The right dress is more than a piece of fabric—it’s your confidence boost, your “let’s make some memories” mood, and your passport to turning every moment into a photo op. Windsor vacation dresses are made for the girl who wants to live boldly and look unforgettable doing it. Think flowy silhouettes that catch the wind just right, playful cutouts that keep things spicy, and luxe touches like lace, ruching, or shimmer that make you feel like you’re on your own runway. These dresses are designed to travel with you, wrinkle-resistant and easy to style up or down, so you can pack light and play hard. And if you’re shopping for a gift? Trust, vacation dresses are the ultimate “you deserve this” surprise for your bestie, your sister, or any queen who’s overdue for a little escape.
Choosing women’s Windsor dresses for your next adventure is all about matching your vibe to your destination—and your mood. Maybe you’re a beach babe who lives for breezy maxis, or a city explorer who loves a flirty mini that moves with you from brunch to nightlife. Or perhaps you’re the friend who’s always snapping candids, in which case, you know a bold print or a pop of color is non-negotiable. Windsor vacation is about options, so you can switch it up as often as your itinerary changes. Don’t forget the details: smocked waists for comfort on those long travel days, adjustable straps for the perfect fit, and pockets (because who has time for a purse when you’re living your best life?). And let’s be real—these dresses aren’t just for tropical escapes. They’re made for staycations, spontaneous road trips, or even just making an ordinary day feel like a getaway. If you’re looking to level up your wardrobe with pieces that work just as hard as you play, check out our Cute Vacation Dresses for inspo that’s as fresh as your passport stamp collection.
Every Windsor girl knows that the right vacation dress doesn’t just fit your body—it fits your story. Whether you’re gifting a little wanderlust to your ride-or-die or treating yourself to something special “just because,” Windsor vacation dresses are your go-to for turning every destination into a celebration. They’re made for the girl who wants to stand out, who’s not afraid to twirl on the dance floor or take the scenic route home. With the perfect dress, you’re ready for anything: rooftop dinners, barefoot beach walks, spontaneous detours, and all those little moments that make a trip unforgettable. So, pack your bags, grab your girls, and get ready to take on the world—one iconic outfit at a time.