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 bronze knit maxi dress featuring a trendy lace-up back and flattering bodycon silhouette.
$49.90
A sage sleeveless skater dress featuring a ruffled lace silhouette and adjustable spaghetti straps.
$38.90
An airy white eyelet knit skater dress with adjustable straps and a flowy fit-and-flare silhouette.
$39.90
A brown knit midi dress with long sleeves, off-the-shoulder neckline, and ruched bodycon fit.
$32.90
A strapless yellow mini dress with ruched sides and a playful ruffled hem in knit fabric.
$34.90
A black abstract floral mini dress featuring a cowl halter neckline and ruffled slit design.
$48.90
A flirty white mini skater dress featuring breezy eyelet knit fabric and a charming tie-back detail.
$36.90
A lavender ribbed knit mini dress with a scoop neckline and flattering skater silhouette.
$54.90
An ivory floral satin dress with a lace-up back and flirty A-line silhouette.
$59.90
A dreamy white floral maxi dress with an open tie back and ruffled silhouette.
$35.90
A bold yellow floral mini dress featuring a strapless neckline and high-stretch knit fabric.
$49.90
An A-line midi dress in natural woven fabric with a smocked bodice, pleats, and hidden pockets.
$34.90
A strapless red mini dress with an abstract floral print, side ruching, and an A-line silhouette.
$39.90
A vibrant yellow mesh mini dress featuring all-over ruching and a strapless bodycon silhouette.
$49.90
A lavender glitter skater dress with sheer peasant sleeves and a fit and flare silhouette.
$49.90
A natural floral skater dress featuring a corset-inspired bodice, pleated trim, and cotton woven fabric.
$32.90
A breezy white eyelet knit skater dress featuring a square neckline and double-layered flared skirt.
$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.
$46.90
An ivory striped midi dress with cutouts, adjustable straps, and dual side slits for casual elegance.
$34.90
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.
$44.90
A yellow crochet knit midi dress featuring a high halter neckline and form-hugging silhouette.
$39.90
A sheer white crochet knit cover up dress featuring a plunge neckline, hoop insert, and long flare sleeves.
$34.90
An orange abstract print mini dress featuring sheer mesh, halter neckline, side cutouts, and open back.
$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.
$19.97 $39.90 50% off
A khaki woven midi dress with a smocked bodice, ruffled hem, and dual spaghetti straps.
$39.90
A mauve floral off-shoulder bodycon dress in stretchy knit fabric with soft ruching and flared hem.
$39.90
An ivory satin mini dress featuring a tropical floral print, strapless neckline, and flowy A-line silhouette.
$42.90
A blue paisley halter mini dress featuring a smocked bust, ruffled hem, and flowy woven fabric.
$39.90
A white eyelet lace mini dress with ruffled straps and a ruched sweetheart neckline.
$42.90
An olive green gauze skater dress featuring a V-neckline, open cross-back, and ruffled hem.
$44.90
A girly green gingham mini dress with smocked cotton fabric, ruffled details, and adjustable straps.
$28.90
A black gauze midi dress featuring a sleeveless V-neck, adjustable straps, low back, and side pockets.
$35.90
An olive green tropical print mini dress featuring a V-neckline, twisted bust, and strappy tie-back.
$36.90
A pink floral mesh mini dress featuring a strapless neckline and asymmetric ruffled bodycon silhouette.
$46.90
An olive green gauze skater dress featuring V-neck cutouts, flowy sleeves, and a breezy silhouette.
$42.90
A black tropical floral maxi dress featuring a square halter neckline, criss-cross back, and high side slit.
$44.90
A rust-colored one-shoulder maxi dress with a tropical print, side cutout, and high slit.
$59.90
An ivory A-line maxi dress with gauze fabric, sheer lace insets, and a faux leather belt.
$39.90
A brown knit maxi dress featuring a halter neckline, shimmering stone hardware, and bold cutout accents.
Now Trending
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: XL | 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
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 Natural | Size: XS | 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
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
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
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
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 Wine | Size: M | 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
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.