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
A denim satin mini dress with a ruched wrap silhouette and spaghetti straps for a chic look.
$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.
$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.
$32.90
A breezy white eyelet knit skater dress featuring a square neckline and double-layered flared skirt.
$49.90
A lavender glitter skater dress with sheer peasant sleeves and a fit and flare silhouette.
$59.90
An ivory A-line maxi dress featuring gauze fabric, sheer lace insets, and a faux leather belt.
$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.
$20.97 $46.90 55% off
An abstract red knit maxi dress featuring a cowl neckline, hoop trims, strappy back, and high side slit.
$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.
$39.90
A sheer white crochet knit cover-up dress with long sleeves, plunge neckline, and chic hoop insert.
$39.90
A white eyelet lace mini dress with ruffled straps and a ruched sweetheart neckline.
$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 vibrant pink mini dress featuring a leopard snake print, mesh fabric, side cutout, and ruffled slit.
$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.
$20.97 $46.90 55% off
An olive green gauze skater dress featuring V-neck cutouts, flowy sleeves, and a breezy silhouette.
$9.97 $37.90 74% off
An ivory floral bodycon mini dress featuring a strapless neckline and flirty ruffled hem.
$36.90
An abstract rust mesh mini dress featuring a cowl halter neckline, cutout bodice, and ruffled 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.
$38.90
A pink floral mesh midi dress featuring a strapless neckline and curve-hugging fit for elegant occasions.
$44.90
A white floral chiffon skater dress featuring charming ruffles, a strapless neckline, and a smocked bodice.
$64.90
A blue floral bodycon mini dress featuring ruffled hem, square neckline, and stretch woven fabric.
$19.97 $39.90 50% off
A natural paisley maxi dress featuring mesh fabric, a bodycon silhouette, and a high side slit.
$26.90
A taupe plaid mini dress with a V-neckline, spaghetti straps, and a bodycon silhouette.
$9.97 $52.90 81% off
A light blue strapless mini dress featuring eyelet woven fabric, a smocked bodice, and ruffled hem.
$9.97 $49.90 80% off
A floral ivory mini dress featuring a corset bodice, lace-up back, and adjustable spaghetti straps.
$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.
$39.90
A sultry black formal dress with rhinestone straps, cowl neckline, and a high slit.
$46.90
A chic black bodycon midi dress with a square neckline and stretchy double-lined knit fabric.
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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 Light Blue | Size: L | 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: L | Knit 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
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 Pink | Size: S | Knit Fabric/Satin 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
Capture all the attention with your sultry allure in the Paige rhinestone formal bodycon mini dress! She features a sleeveless cowl neckline, adjustable spaghetti straps for a customized fit, all-over rhinestone embellishments for that total glam girl vibe, a mini-length hem, and a bodycon silhouette to hug your gorgeous curves. The slinky knit fabric offers plenty of stretch. Style this mini dress with metallic heels for your next dressy night out! Fit & FeaturesSleeveless cowl neckline, Adjustable spaghetti straps, All-over rhinestone embellishments, Mini-length hem, bodycon silhouette, Slinky knit fabric, full-length knit lining, plenty of stretch, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Paige Rhinestone Formal Bodycon Mini Dress in Red | Size: XS | Knit Fabric/Rhinestone
This chic side slit knit mini skirt will give you a fabulous fit and become a favorite in your closet! The ponte knit fabric offers a structured fit with moderate stretch. The high waist features an elasticized waistband for comfortable wear, while the mini-length hem and side slit accent will give that sultry flair. The bodycon silhouette will hug your gorgeous curves. Style this mini skirt with a basic bodysuit and ankle booties for happy hour. Fit & FeaturesPonte knit fabric, moderate stretch, High-rise elasticized waist, Mini-length hem, Asymmetric seam, side slit, Bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fabulous Fit Side Slit Knit Mini Skirt in Black | Size: L | Knit Fabric
Windsor Brenda Low Back Bow Taffeta Skater Dress in Black
$19.97 $64.90
69% off
Chat, dance, and twirl the night away in the Brenda taffeta skater dress! The short dress is ready to party with a voluminous silhouette and a stunning low-cut back with a statement bow. Fit & FeaturesTaffeta fabric lined with tulle, stretchy knit fabric, Tank shoulder straps, Low back with bow, Skater silhouette, Short-length hem, Runs true to size, Where to Wear:Prom, brides, weddings, bridesmaids, fancy date nights, dinner parties, cocktail events Free Shipping on All Orders Over $75. | Windsor Brenda Low Back Bow Taffeta Skater Dress in Black | Size: XS | Knit Fabric
A sassy mini dress to slip on when the sun goes down and the beat is calling you to the dancefloor! This dress is featured in a sultry bodycon silhouette with a halter neckline accented with hoop inserts. Fit & FeaturesAbstract print, stretchy knit fabric, Cowl halter neckline, hoop accents, Bodycon silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sun Goes Down Halter Abstract Bodycon Mini Dress in Brown | Size: S | Knit Fabric
Here comes the sun and you radiating trendy vibes in this strapless mini dress perf for casual plans! The ruched sides and ruffled hem add a playful touch to the bodycon silhouette. Fit & FeaturesDouble-lined brushed knit fabric, moderate stretch, Strapless straight neckline, Ruched side seams, Bodycon silhouette, Mini-length tiered ruffled hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Here Comes The Sun Strapless Ruffled Mini Dress in Brown | Size: S | Knit 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.