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.

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Windsor Exceptional Off-The-Shoulder Flared Midi Dress in Natural

$36.90

An elegant off-the-shoulder natural midi dress with a stretchy knit fabric and flared hem.

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.

Into The Sun V-Neck Maxi Dress in Natural

$45.90

A natural-hued maxi dress featuring a textured knit fabric, V-neckline with metal accent, and body-skimming silhouette.

Vacay Beauty Strappy Back Floral Maxi Dress in Natural

$39.90

A natural floral maxi dress featuring a strappy back, mesh overlay, and curve-hugging fit.

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 Cozy Flair Striped Knit Off-The-Shoulder Mini Dress in Ivory

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Windsor Cozy Flair Striped Knit Off-The-Shoulder Mini Dress in Ivory

$9.97 $32.90 70% off

An ivory off-the-shoulder mini dress in striped ribbed knit offers cozy flair and stretch.

The Essential High-Slit Ribbed Knit Midi Dress in Black

$42.90

A black ribbed knit midi dress featuring a turtleneck, long sleeves, and a high side slit.

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.

Windsor Desert Sun Lace Ruffle Mini Dress in Ivory

$39.90

An ivory lace mini dress with a form-hugging fit and shark bite ruffle hem.

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Mayra Formal Satin Slit Long Dress in Navy Blue-2

$29.97 $59.90
50% off

(184)

Slip into the luxe vibes of Mayra! Designed to highlight your figure, this formal satin dress delivers a chic form-hugging fit and a high slit for effortless movement. Fit & FeaturesSmooth satin-knit fabric, moderate stretch, Sleeveless square neckline, spaghetti straps, Fitted bodice, side hip pleating, Form-fitting silhouette, high-cut front slit, Floor-length hem, Style runs small, Where to Wear:Homecoming, weddings, black-tie parties, galas, military balls, engagement parties, rehearsal dinners, bridal celebrations, birthday events, milestone celebrations Free Shipping on All Orders Over $75. | Windsor Mayra Formal Satin Slit Long Dress in Navy Blue-2 | Size: M | Satin Fabric

Sasha Formal High Slit Wrap Dress in Black

$39.90

(174)

Create a captivating entrance in this formal wrap dress for your next soiree. All eyes are on you in this stylishly chic long formal dress with a plunging V-neckline to perfectly display a sparkling rhinestone lariat or delicate layers of dainty necklaces. Fit & FeaturesCrepe fabric, moderate stretch, Asymmetrical wrap V-neckline, Adjustable spaghetti straps, Ruched detailing, slim-fit bodice, High front slit, floor-length wrap silhouette, Runs true to size, Where to Wear:Prom, black-tie weddings, and formal parties. Free Shipping on All Orders Over $75. | Windsor Sasha Formal High Slit Wrap Dress in Black | Size: M | Rhinestone

Windsor Rowena Sequin Mermaid Dress in Navy Blue

$109.90

(168)

Chic and glamorous, the Rowena sequin mermaid long dress will stylishly elevate your formal night-out look. With a lace-up strap design and fitted mermaid silhouette with a high slit, you'll deliver stunning style. Fit & FeaturesSheer mesh fabric, knit lining, moderate stretch, embroidered sequin scroll design, Sleeveless square neckline, padded bust, Spaghetti straps, open back, lace-up strap design, tie closure, Lower back zipper with hook and eye closure, High waist seam, Fitted floor-length mermaid silhouette, high front slit, Runs true to size, Where to Wear:Prom, black-tie parties and galas, fancy engagement parties Free Shipping on All Orders Over $75. | Windsor Rowena Sequin Mermaid Dress in Navy Blue | Size: M | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric

Windsor Cheyenne Formal One-Shoulder Velvet Dress in Black

$59.90

(130)

Lavish yourself with a luxe formal dress that elevates your special occasion outfit! Cheyenne features a one-shoulder neckline, a wired V-neck bust, a fitted long sleeve, a high side slit on the floor-length hem, and a curve-hugging A-line silhouette. The long dress is composed of a lined velvet fabric that offers a moderate stretch. Complete the look with rhinestone heels and a sphere clutch. Fit & FeaturesOne-shoulder neckline, wired V-neck bust, Fitted long sleeve, High side slit, floor-length hem, A-line silhouette, Lined velvet fabric, Form-hugging fit, moderate stretch, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cheyenne Formal One-Shoulder Velvet Dress in Black | Size: S | Rhinestone/Velvet Fabric

Bethanie Formal Sequin V-Neck Mermaid Dress in Pink-2

$109.90

(93)

Embellished with light-catching sequins, the Bethanie formal dress is a clear stunner with a lace-up back and a flattering mermaid silhouette with a floor-length hem. Fit & FeaturesSequin-scroll pattern, mesh fabric, stretch knit lining, Sleeveless V-neckline, padded bust, Lace-up back, zipper and hook-eye closure, Mermaid silhouette, Floor-length hem, Runs true to size, Where to Wear:Formal dances, black-tie events, formal weddings, and upscale parties. Free Shipping on All Orders Over $75. | Windsor Bethanie Formal Sequin V-Neck Mermaid Dress in Pink-2 | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric

Shayla Strapless Corset Lace Formal Dress in Red

$159.90

(75)

Designed to be eyed up and down, the Shayla long formal dress brings the sultry heat to any black-tie occasion! A curved neckline and sheer mesh lace corset bodice create a sophisticated silhouette, while the lace-up back provides a personalized fit. Fit & FeaturesSheer mesh, smooth knit fabric, Lace corset bodice, flexible boning, padded bra cups, Lace-up, back zipper with hook-eye closure, Floor-length fitted silhouette, high front wrap slit, Runs true to size, Where to Wear:Formal dances, black-tie galas, red-carpet occasions, and big birthday events, weddings, bridal showers, engagement parties, rehearsal dinners. Free Shipping on All Orders Over $75. | Windsor Shayla Strapless Corset Lace Formal Dress in Red | Size: S | Knit Fabric/Sheer Mesh Fabric

Windsor Jamie Lace-Up Satin Formal Column Dress in Brown

$89.90

(73)

Dare to stun in the Jamie satin formal dress crafted with silky satin fabric for a gorgeous sheen. The bold plunge halter neckline and open lace-up back will turn heads while the fitted column silhouette flaunts your curves. Fit & FeaturesSilky satin fabric, short knit stretchy lining, Plunge halter V-neckline, shoulder straps, padded bra cups, Lace-up open back, lower zipper with hook-eye closure, High side slit, Fitted column silhouette, Floor-length hem, Runs true to size, Where to Wear:Prom, weddings, galas, and black-tie soirees. Free Shipping on All Orders Over $75. | Windsor Jamie Lace-Up Satin Formal Column Dress in Brown | Size: S | Knit Fabric/Satin Fabric

Amirah Formal Glitter Cowl Neck Column Dress in Green

$59.90

(73)

Look your best for a fancy night in the stunning Amirah formal glitter dress! Fashioned with an eye-catching cross back, this dress will make you feel like the star of the evening with a high slit and floor-length column silhouette. Fit & FeaturesGlitter knit fabric, moderate stretch, Sleeveless cowl neckline, Spaghetti straps, cross back, Side pleated seam, slim silhouette, high front slit, Floor-length column silhouette, Runs true to size, Extra glitter for maximum sparkle - may have some natural fallout, Where to Wear:Prom, black-tie weddings, galas, and upscale birthday events. Free Shipping on All Orders Over $75. | Windsor Amirah Formal Glitter Cowl Neck Column Dress in Green | Size: XS | Knit Fabric

Rose Formal Mesh Corset Column Dress in Brown

$54.90

(72)

The Rose formal long column dress is the perfect combination of elegance and glamour with a sheer corset trim and high-side slit for effortless allure! Fit & FeaturesMesh fabric, partial stretchy knit lining, Sleeveless sweetheart neckline, cowl pleating, Adjustable spaghetti straps, crisscross open back, Padded bust, sheer corset bodice, flexible boning, Side ruched seams, fitted column silhouette, High-side slit, floor-length hem, Style runs small, Where to Wear:Prom, weddings, bridesmaids, rehearsal dinners, cocktail soirees, and dressed-up date nights. Free Shipping on All Orders Over $75. | Windsor Rose Formal Mesh Corset Column Dress in Brown | Size: XS | Knit Fabric/Mesh Fabric

Windsor Savannah Formal Crepe Long Dress in Black

$49.90

(66)

Stunning for brides and celebrations, the Savannah formal crepe dress showcases simplicity and chicness! With a form-hugging silhouette and sultry high front slit, this formal dress is perfect for an evening of elegance. Fit & FeaturesLined crepe fabric, moderate stretch, Sleeveless square neckline, tank-style straps, Back zipper and hook-eye closure, Form-hugging silhouette, Front high-cut slit, Floor-length hem, Runs true to size, Where to Wear:Prom, weddings, bridesmaids, red-carpet events, milestone celebrations Free Shipping on All Orders Over $75. | Windsor Savannah Formal Crepe Long Dress in Black | Size: XS

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.

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Women's Vacation Dresses

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Women's Vacation Dresses

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