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.

Show Filters

Sort: Recommended

Size

Color

Price

All Filters

27 results

Sort

Windsor Perfectly Stylish Sleeveless Ribbed Knit Midi Dress in White

$38.90

A white sleeveless ribbed knit midi dress featuring a V-neckline and chic high front slit.

Windsor Pretty Vibes Eyelet Knit Layered Skater Dress in White-2

$32.90

A breezy white eyelet knit skater dress featuring a square neckline and double-layered flared skirt.

Windsor Floral Charm Ruffled Chiffon Tube Skater Dress in White

$44.90

A white floral chiffon skater dress featuring charming ruffles, a strapless neckline, and a smocked bodice.

Windsor Dovie Sequin Beaded Mesh Column Dress in Peach

$149.90

A peach column dress with sequin beaded mesh, adjustable straps, and a high side slit.

Now Trending

Windsor Perfectly Stylish Sleeveless Ribbed Knit Midi Dress in White

$38.90

(46)

Achieve a perfectly stylish everyday look with this sleeveless ribbed knit midi dress! Designed with a comfortable ribbed knit fabric offering plenty of stretch, it features a V-neckline, spaghetti straps, a midi-length hem with a chic high front slit, and a form-hugging silhouette. Pair with a cropped denim jacket and clear mules. Fit & FeaturesStretchy ribbed knit fabric, V-neckline, Spaghetti straps, High front slit, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Perfectly Stylish Sleeveless Ribbed Knit Midi Dress in White | Size: L | Knit Fabric

Windsor Smooth Talker Strapless Bodycon Midi Dress in Brown

$33.90

(17)

Show off your smooth moves in this strapless bodycon midi dress perfect for dressing up or down for any occasion! Fit & FeaturesRib knit fabric, sewn-in knit lining, moderate stretch, Strapless neckline, Side slit, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Smooth Talker Strapless Bodycon Midi Dress in Brown | Size: L | Knit Fabric

Windsor Curve Flow Bodycon Midi Dress in Black

$42.90

(7)

Sleek, soft, and made to flatter. This mock neck midi dress hugs in all the right places with side ruching and a soft modal blend knit fabric that gives casual polish. Perfect for weekday styling and weekend looks! Fit & FeaturesSoft modal-blend knit fabric, knit lining, moderate stretch, Sleeveless mock neck, Side ruched seams, Bodycon fit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Curve Flow Bodycon Midi Dress in Black | Size: XS | Knit Fabric

Sale

Windsor Moonlit Bloom Abstract Floral Maxi Dress in Brown

$35 $49.90
30% off

(6)

Slip into something sleek—this mesh maxi dress flaunts an abstract floral print that gives the illusion of an hourglass figure for an effortless allure at every event you're seen at! Fit & FeaturesAbstract floral print, mesh-lined stretch fabric, Scoop neckline, Spaghetti straps, Curve-hugging silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Moonlit Bloom Abstract Floral Maxi Dress in Brown | Size: XS | Mesh Fabric

Windsor Pretty Vibes Eyelet Knit Layered Skater Dress in White-2

$32.90

(5)

Show off pretty vibes in this adorable layered skater dress made with breezy eyelet knit fabric. Pair with sneakers for a cute casual look or wedges for a dressier style. Fit & FeaturesStretchy sheer eyelet knit fabric, partial knit lining, Square neckline, Spaghetti straps, Double-layered skater skirt, Short fit-and-flare silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Pretty Vibes Eyelet Knit Layered Skater Dress in White-2 | Size: M | Knit Fabric

Total Attraction Cutout Bodycon Midi Dress in White

$42.90

(4)

Look and feel like a babe in this bodycon midi dress with a flirty cutout twist back design and side slit for effortless movement! Pair with cute sandals. Fit & FeaturesTexture knit fabric, stretchy knit lining, Scoop neckline, spaghetti straps, Twist cutout back design, Side slit, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Total Attraction Cutout Bodycon Midi Dress in White | Size: M | Knit Fabric

Windsor Written In Roses Strapless Midi Dress in Red

$34.90

(4)

This one doesn’t rush—it lingers. A strapless silhouette with a fluid floral print and front slit that moves easily, feels confident, and looks unforgettable from every angle. Fit & FeaturesFloral print, mesh-lined stretchy fabric, Strapless neckline, Front slit for movement, Curve-hugging midi-length silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Written In Roses Strapless Midi Dress in Red | Size: M | Stretchy Fabric

Sale

Windsor Chic Paradise Halter Open Back Slit Midi Dress in Red Brown

$32 $45.90
30% off

(4)

Own the spotlight on vacation in this midi dress! Featuring a bold halter neckline and an sexy open back, this dress exudes allure, while the bodycon silhouette and slit add a flattering look. Fit & FeaturesSlinky knit fabric, smooth stretchy knit lining, Halter cowl neckline, beaded spaghetti strap tie, Open back with spaghetti strap tie, Bodycon silhouette, Slit accent, midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Paradise Halter Open Back Slit Midi Dress in Red Brown | Size: XS | Knit Fabric

Windsor Majorly Chic Ribbed Knit Mock Neck Midi Dress in Ivory

$42.90

(3)

Meet the midi dress that makes minimal feel major. The mock neck and keyhole detail bring a chic vibe, while the ribbed knit stretch keeps it comfy enough from brunch meet-ups to dinner dates. Fit & FeaturesRibbed hacci knit fabric with knit lining, high stretch, Sleeveless mock neckline, Keyhole cutout at the bust, Angled seams under the bust, Midi-length bodycon silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Majorly Chic Ribbed Knit Mock Neck Midi Dress in Ivory | Size: L | Knit Fabric

So Loved Tube Bodycon Midi Dress in Black

$39.90

(3)

Love at first wear...this tube midi dress elevates your everyday look with curve-accentuating side ruched seams, a bodycon fit, and a side slit for movement. Fit & FeaturesStretchy rib knit fabric, knit lining, Strapless tube neckline, Side ruched seams, Bodycon silhouette, Side slit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Loved Tube Bodycon Midi Dress in Black | Size: XL | Knit Fabric

Women's Vacation Dresses

Vacation dresses aren’t just something you pack—they’re your ticket to feeling a little lighter, a little brighter, and a whole lot more yourself, no matter where your out-of-office reply takes you. Whether you’re jetting off to chase the sun in the middle of January or plotting a weekend staycation that feels like a total reset, the right dress can turn every moment into a memory (and every photo into a favorite). Think breezy fabrics that catch the ocean breeze, silhouettes that let you move from café to coastline without missing a beat, and details that make you feel instantly pulled together—even when you’re living out of a suitcase. Windsor vacation dresses are designed for the girl who wants to look effortless but never forgets about comfort. Imagine slipping into a flowy maxi after a day of sightseeing, or throwing on a flirty mini for spontaneous plans that turn into late-night adventures. These dresses aren’t just about looking good for the ‘gram—they’re about feeling easy, unbothered, and ready for whatever the day (or night) brings.

Shopping for vacation dresses is as much about anticipation as it is about practicality. You’re picturing yourself at golden hour, drink in hand, or wandering through a local market with a tote full of treasures. Maybe you’re searching for something versatile enough to double as a cover-up by day and a dinner look by night, or you want a dress that packs down to nothing but still makes you feel like your best self. Lightweight materials, wrinkle-resistant finishes, and adjustable fits are your best friends for travel—because who has time for high-maintenance when the world is calling? These dresses also make the perfect gift for anyone with wanderlust on their mind: your best friend prepping for her first solo trip, your sister who’s always planning the next girls’ getaway, or even yourself, because sometimes you need to celebrate booking the flight (or surviving another week at work). The beauty of a vacation dress is in its flexibility—dress it up with a statement earring and strappy sandals, or keep it casual with sneakers and a denim jacket. And if you’re headed somewhere warm while everyone else is bundled up, there’s something undeniably satisfying about stepping out in something bold and breezy while the rest of your feed is still in sweater mode. For more laid-back options that still deliver on style, check out our curated collection of Casual Vacation Dresses—because sometimes the best memories start with the simplest outfits.

At the end of the day, vacation style is all about embracing the unexpected—last-minute plans, weather that doesn’t check the forecast, and those moments when you realize the best nights are the ones you didn’t overthink. That’s why Windsor vacation dresses are built for spontaneity and self-expression, letting you lean into whatever vibe you’re chasing. Maybe you’re drawn to bold prints that pop against a tropical backdrop, or you prefer soft, romantic hues for sunset dinners and slow mornings. The right dress lets you switch up your mood as easily as you swap out accessories, and it’s always ready for a change of scenery. These are the pieces you reach for when you want to feel a little more alive, a little more adventurous, and a lot more like the main character in your own story (without ever having to say it out loud). Whether you’re gifting one to a friend or treating yourself to a pre-trip wardrobe refresh, a vacation dress is more than just a packing list essential—it’s a reminder that every day can feel like an escape, even if you’re just exploring your own city. So go ahead—lean into the carefree spirit, embrace the ease, and let your dress do the talking while you soak up every moment.

Reset Your Password

Email Sent

Order Status

Women's Vacation Dresses

Home Women's Vacation Dresses

Now Trending

Women's Vacation Dresses

Related Collections