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.
$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.
$59.90
A white mini dress with iridescent sequins, sheer velvet fabric, and adjustable spaghetti straps.
$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.
$39.90
A brown knit midi dress with long sleeves, off-the-shoulder neckline, and ruched bodycon fit.
$54.90
An ivory floral satin dress with a lace-up back and flirty A-line silhouette.
$48.90
A flirty white mini skater dress featuring breezy eyelet knit fabric and a charming tie-back detail.
$49.90
An ivory mesh midi dress with a dainty floral print, ruched seams, and a draped cowl neckline.
$6.97 $46.90 85% off
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.
$49.90
A lavender glitter skater dress with sheer peasant sleeves and a fit and flare silhouette.
$9.97 $52.90 81% off
A strapless ivory chiffon skater dress with a ruffled silhouette and stretchy smocked bodice.
$19.97 $44.90 56% off
A black one-shoulder tropical maxi dress with a ruffled slit and metal-accented strap.
$59.90
An ivory A-line maxi dress with 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.
$20.97 $46.90 55% off
An abstract red knit maxi dress featuring a cowl neckline, hoop trims, strappy back, and high side slit.
$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.
$9.97 $38.90 74% off
A sultry orange knit midi dress featuring a one-shoulder neckline, front cutouts, and gold O-ring accents.
$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 brown knit maxi dress featuring a halter neckline, shimmering stone detail, and bold cutout accents.
$19.97 $42.90 53% off
A rust floral skater dress in rayon with tie-back halter straps and a breezy fit-and-flare silhouette.
$39.90
A sheer white crochet knit cover up dress featuring a plunge neckline, hoop insert, and long flare sleeves.
$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.
$9.97 $56.90 82% off
An ivory floral skater mini dress with a sweetheart neckline and adjustable spaghetti straps.
$9.97 $42.90 77% off
A blue floral mesh-lined midi dress featuring a twist halter neckline and curve-hugging bodycon silhouette.
$34.90
A chic brown strapless maxi dress with a high slit and flattering bodycon silhouette.
$9.97 $46.90 79% off
A charming floral babydoll mini dress in natural with a flowy ruffled silhouette and smocked bust.
$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.
$44.90
A sultry black floral maxi dress with a V-neckline and form-hugging silhouette, perfect for vacations.
$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.
$44.90
A girly green gingham mini dress with smocked cotton fabric, ruffled details, and adjustable straps.
$36.90
An abstract rust mesh mini dress featuring a cowl halter neckline, cutout bodice, and ruffled slit.
$42.90
A green knit midi dress featuring a strapless sweetheart neckline, pleated overlay, and back slit.
$9.97 $44.90 78% off
A vibrant orange geometric print midi dress in smooth knit fabric with a halter neckline and open back.
$38.90
A vibrant pink mini dress featuring a leopard snake print, mesh fabric, side cutout, and ruffled slit.
$49.90
A brown floral mesh maxi dress featuring a curve-hugging fit and flirty strappy open back.
$19.97 $42.90 53% off
A royal blue tropical print maxi dress featuring a lace-up back, high side slit, and stretchy knit fabric.
$39.90
An ivory lace skater dress with an off-the-shoulder neckline and sheer long fitted sleeves.
$38.90
A pink floral mesh midi dress featuring a strapless neckline and curve-hugging fit for elegant occasions.
$9.97 $52.90 81% off
An ivory chiffon babydoll dress featuring a floral print, ruffled shoulder straps, and a square neckline.
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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: XL | 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
The mini dress features a sleeveless square neckline with a pleated bust, spaghetti straps, and an A-line silhouette. Complete outfit with a sleek rhinestone clutch. Fit & FeaturesSmooth knit fabrication, Sleeveless square neckline, Pleated bust, Spaghetti straps, A-line silhouette, Mini length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Sophistication A-Line Pleated Mini Dress in Denim | 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
Women's Vacation Dresses
When it comes to planning the ultimate getaway, nothing sets the vibe quite like curating the perfect collection of vacation dresses for women. Whether you’re jetting off to a tropical paradise, hopping aboard a cruise, or just plotting a weekend escape with your besties, the right dress is your ticket to feeling fearless, flirty, and totally unbothered. Think breezy silhouettes that catch the ocean breeze, flowy fabrics that keep you cool while you dance under the stars, and vibrant prints that pop against every Insta-worthy backdrop. These are the pieces that turn a simple stroll down the boardwalk into a main character moment, or a sunset dinner into a scene you’ll replay on your camera roll all year. The Windsor vacation collection is all about capturing those carefree vibes—easy to pack, effortless to style, and always ready for a little adventure. If you’re shopping for yourself, it’s your chance to treat yourself to that “I’m on vacation, don’t text” energy. But let’s be real: vacation dresses make the ultimate gift for your ride-or-die girls too. Surprise your sister before her bachelorette weekend, spoil your best friend before her big birthday trip, or just send a little sunshine to someone who deserves a break. These dresses are made for making memories, and every time she wears it, she’ll think of you (and probably send you a fire selfie as a thank you).
Choosing the right Windsor vacation dresses is about more than just looking cute (though, trust, you’ll look *so* cute). It’s about feeling unstoppable, wherever the day—or night—takes you. Look for lightweight, wrinkle-resistant fabrics that can survive even the most chaotic suitcase situations, and details like adjustable straps or smocked waists that keep things comfy from sunrise to last call. If you’re planning to hit up a fancy dinner, opt for a midi with a flirty slit or a bold color that turns heads the second you walk in. Beach day on the agenda? Go for something flowy and easy to slip on over your swimsuit, with a print that matches your mood (and your margarita). And don’t forget about versatility: the best vacation dresses for women can be styled up or down with just a swap of shoes or a quick change of accessories. That’s the secret sauce to packing light and still serving a new look every day. Whether you’re living it up on a Windsor vacation or just dreaming of your next escape, these dresses are your invitation to step out of your comfort zone and into your main character era. Ready to find your next getaway obsession? Explore our handpicked edit of Cute Vacation Dresses and get ready to make every day feel like a holiday.