Elegant Vacation Dresses
Get ready to turn every tropical escape into your personal runway with our collection of elegant vacation dresses. Whether you're sipping cocktails by the beach or dancing under the stars, these dresses are your ticket to effortless glam. Picture yourself in flowy silhouettes and vibrant hues that capture the essence of sun-kissed days and balmy nights. From breezy maxis to chic minis, each piece is designed to make you feel like the queen of paradise. So pack your bags, grab your sunnies, and let these stunning styles take you from poolside lounging to evening adventures with ease.
$34.90
A black abstract floral mini dress featuring a cowl halter neckline and ruffled slit design.
$42.90
An ivory knit midi dress with a sleeveless cowl neckline and chic high front slit.
$59.90
A white mini dress with iridescent sequins, sheer velvet fabric, and adjustable spaghetti straps.
$54.90
A lavender mesh corset column dress featuring a sweetheart neckline and high-side slit for elegance.
$54.90
A stunning mauve satin gown with a cowl neck, high slit, and sleek spaghetti straps.
$36.90
An elegant sage off-the-shoulder midi dress with a bodycon fit and flared hem.
$19.97 $29.90 33% off
A strapless black floral maxi dress with a front slit and comfortable stretchy knit fabric.
$109.90
A black sequin bodycon dress with a high slit, adjustable straps, and padded bust for formal events.
$46.90
A sultry brown maxi dress featuring a twist plunge V-neckline, cutout bodice, and ruffled slit.
$42.90
A navy blue velvet midi dress with a sleeveless sweetheart neckline and pleated bodice.
$69.90
A blue floral crepe mermaid dress with a sweetheart neckline and high front slit.
$59.90
A white floral maxi dress with a ruffled silhouette and charming open tie back design.
$46.90
An ivory striped midi dress with cutouts, adjustable straps, and dual side slits for casual elegance.
$42 $59.90 30% off
A white crepe formal dress featuring adjustable straps, ruffle trim, and a dramatic high front slit.
$45.90
An elegant white satin midi dress with a strapless cowl neckline and form-hugging fit.
$149.90
A peach column dress with sequin beaded mesh, adjustable straps, and a high side slit.
$44.90
A black one-shoulder tropical maxi dress with a ruffled slit and metal-accented strap.
$64.90
A wine velvet mermaid dress with a chic ruched halter neckline and partially open back.
$99.90
A sage sequin mesh mermaid dress with a sweetheart neckline and adjustable spaghetti straps.
$20.97 $46.90 55% off
An ivory chiffon skater dress featuring a smocked bodice, cutout accent, and breezy long sleeves.
$49.90
An ivory off-the-shoulder pleated maxi dress with a flowy silhouette and drop waist seam.
$28 $39.90 30% off
A khaki woven midi dress with a smocked bodice, ruffled hem, and dual spaghetti straps.
$79.90
An ivory mesh mermaid dress with faux pearls, off-the-shoulder neckline, and high side slit.
$69.90
A green satin midi dress with a lace-up back and faux wrap bodycon silhouette.
$26.97 $59.90 55% off
A chic black V-neck maxi dress with color block panels and trendy spaghetti straps.
$26.97 $59.90 55% off
A chic black satin maxi dress with a halter neckline and high front slit for bold elegance.
$59.90
An ivory A-line maxi dress with gauze fabric, sheer lace insets, and a faux leather belt.
$69.90
A shimmering green glitter knit mermaid dress with an off-the-shoulder neckline and sheer ruched sleeves.
$56.90
A black velvet skater dress with a strapless neckline and pleated mini-length hem for formal occasions.
$9.97 $54.90 82% off
A pink satin one-shoulder midi dress with dual adjustable straps and a slim silhouette.
$59.90
A white satin wrap midi dress with a sleeveless cowl neckline and high-side slit.
$79.90
A burgundy formal dress with faux pearl embroidery, sweetheart neckline, and high slit mermaid silhouette.
$19.97 $35.90 44% off
A strapless tropical midi dress in dark marsala with a bodycon silhouette and side slit.
$69.90
A peach glitter knit mermaid dress with a pleated cowl neck and adjustable spaghetti straps.
$22.97 $49.90 54% off
An elegant black mesh midi dress with ruched details, sheer sleeves, and a ruffled hem.
$19.97 $35.90 44% off
A taupe strapless midi dress in tropical print with a form-hugging bodice and flared hem.
$44.90
A sultry black floral maxi dress with a V-neckline and form-hugging silhouette, perfect for vacations.
$64.90
A black knit mermaid dress with an off-the-shoulder neckline and ruched bodice for formal occasions.
$22.97 $49.90 54% off
A light blue chiffon skater dress with polka dots, a V-neckline, and adjustable spaghetti straps.
$59.90
An effortlessly pretty chiffon midi dress with a floral print, ruffled tiers, and smocked details.
$19.97 $44.90 56% off
A pink floral maxi dress with a form-hugging bodice and flowy hem, perfect for special occasions.
$84.90
An elegant ivory bodycon midi dress featuring beaded embellishments, a strapless neckline, and a front slit.
$109.90
An iridescent red column dress with geometric sequin embroidery and a high side slit.
$49.90
A light blue chiffon midi dress with floral print, puff sleeves, and a chic high front slit.
$59.90
A navy blue satin midi dress with a V-neckline, strappy back, and side slit.
$79.90
A glamorous black glitter knit mermaid dress with a ruched wrap-front and high slit.
$46.90
A black velvet midi dress with a metallic floral pattern, mock neckline, and thigh-high side slit.
$39.90
A captivating black crepe wrap dress with a plunging V-neckline and high front slit.
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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: XS | Rhinestone
Sultry and stunning, the Alisha formal dress will keep all eyes on you. With thin rhinestone detailed straps that give effortless sparkle and a curve-hugging silhouette, and an alluring high slit. Fit & FeaturesLightweight, breathable stretchy fabric, Sleeveless cowl neckline, Rhinestone detailed straps, High waist seam, Floor-length hem, form-fitting silhouette, high slit, Runs true to size, Where to Wear:Prom, glamorous evenings, dinner parties, weddings Free Shipping on All Orders Over $75. | Windsor Alisha Rhinestone Strap Formal Dress in Burgundy | Size: S | Stretchy Fabric/Rhinestone
Ella Cowl Neck Satin Dress in Orange
$19.97 $54.90
64% off
Enchant the room instantly in this gorgeous floor-length gown! Ella features a stunning sleeveless cowl neck, flattering high slit, and sleek spaghetti straps. Fit & FeaturesStretch satin lined fabric, Cowl neck, sleek spaghetti straps, Form-fitting silhouette, high-side slit, Floor-length hem, Runs true to size, Where to Wear:Prom, weddings, bridesmaids, fancy date nights, cocktail parties, engagement parties, rehearsal dinners Free Shipping on All Orders Over $75. | Windsor Ella Cowl Neck Satin Dress in Orange | Size: S | Satin Fabric
Charming Presence Strapless Slit Floral Maxi Dress in Black
$19.97 $29.90
33% off
Your presence will always be charming in this ditsy floral maxi dress at wedding showers, brunch, or casual parties! Adorned in a stunning disty floral print, this strapless dress features a ruffle trim neckline and padded bra cups for flattering support. The curve-hugging silhouette, front slit, and maxi-length hem create a captivating look, while the brushed knit stretchy fabric ensures comfort. Pair with earrings and strappy sandals. Fit & FeaturesDitsy floral print, Brushed knit stretchy fabric, Padded bra cups, Front slit, Curve-hugging silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Charming Presence Strapless Slit Floral Maxi Dress in Black | Size: M | Knit Fabric/Stretchy Fabric
Get ready to be on island time in this gorg tropical floral mesh maxi dress perf for vacay. Featuring a strapless neckline and high side slit, style with heels. Fit & FeaturesSheer mesh fabric with full-length knit lining, high stretch, Large tropical floral print, Strapless straight neckline, High-cut side slit, Maxi-length hem, Form-hugging silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Island Time Tropical Floral Mesh Maxi Dress in Pink | Size: L | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
Love Language Floral Print Mesh Maxi Dress in Pink
$22.97 $49.90
54% off
This airy mesh maxi dress speaks your love language designed with a bold floral print and long fitted silhouette. Style with mules for date night. Fit & FeaturesSheer mesh fabric with full-length knit lining, high stretch, Large floral print, V-neckline, Adjustable spaghetti straps, Maxi-length hem, fitted silhouette, Floral print placement may vary, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Love Language Floral Print Mesh Maxi Dress in Pink | Size: L | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
Gorgeous blooms dance across this floral maxi dress making every entrance statement worthy! Perfect for cocktail parties or dressy dinners, this strapless dress boasts a form-hugging fit, a high side slit allowing for movement, and a maxi-length hem. Complete the look with a clutch purse and heels. Fit & FeaturesFloral print, mesh fabric, stretchy knit lining, Strapless neckline, High side slit, Form-hugging fit, Runs true to size, Please note flower placement may vary, Free Shipping on All Orders Over $75. | Windsor Grandeur Blooms Strapless Slit Floral Maxi Dress in Blue | Size: S | Knit Fabric/Mesh Fabric/Mesh Fabric
A floral print adds to the dreamy charm of this flowy maxi dress boasting an open tie back design and ruffled silhouette perfect for beachside strolls or day parties. Fit & FeaturesFloral print, woven fabric, short woven lining, Sweetheart neckline with bust tie, Spaghetti straps, Open tie back design, Ruffled flowy silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sunshine Dream Open Tie Back Floral Maxi Dress in White | Size: L | Woven Fabric
Impress in this floral maxi dress showcasing a sleek strapless neckline and a column silhouette that flatters your figure. Style the dress with a choker. Fit & FeaturesStatement floral print, Mesh fabric lined with soft, stretch knit, Column silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Impressive Blossom Strapless Floral Maxi Dress in Black | Size: L | Mesh Fabric
Perfect for your vacay in Tulum, this one-shoulder tropical maxi dress was made for sunset dinners and dancing! Fit & FeaturesTropical print, smooth knit fabric with short stretchy lining, One-shoulder neckline, One shoulder strap with metal accents, Front ruffled slit, Bodycon silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor In Tulum One-Shoulder Tropical Maxi Dress in Black | Size: S | Knit Fabric
Elegant Vacation Dresses
When it comes to turning every trip into a main character moment, nothing sets the vibe quite like elegant vacation dresses. Whether you’re jetting off to a dreamy coastal town or plotting a staycation with your crew, these dresses are the secret weapon to looking effortlessly put-together while living your best life. Imagine slipping into a flowy, elegant vacation dress sleeve that catches the breeze just right as you wander through cobblestone streets, or making your grand entrance at a chic rooftop dinner in a gold vacation dress that glimmers with every step. These are the pieces that make packing a thrill—not a chore—because you know you’ll have something for every spontaneous adventure, from sunrise mimosas to late-night star-gazing. They’re not just for the ‘gram, either. Classy vacation dresses are the ultimate confidence boosters, letting you channel that fearless, carefree energy whether you’re exploring new places or just making memories with your favorite people.
Shopping for windsor vacation dresses is all about finding that perfect mix of comfort, style, and versatility—because who has time for wardrobe malfunctions when there are memories to make? Think soft, breathable fabrics that move with you, silhouettes that flatter every curve, and details like delicate straps, playful ruffles, or a daring slit that turns a simple stroll into a runway walk. These dresses make incredible gifts, too. Picture surprising your BFF with a stunning wrap dress for her upcoming getaway, or treating your sister to a piece that’ll have her feeling like a goddess on her next girls’ trip. Even if you’re the one doing the gifting (because, hello, self-love!), there’s something magical about unwrapping a dress that promises new adventures and unforgettable nights. The best part? You don’t have to compromise on style to stay comfy. With options that range from minimalist chic to all-out glam, you can curate a suitcase full of looks that feel as good as they look—so you’re always ready for whatever the itinerary throws your way.
Every trip deserves a wardrobe as bold and vibrant as you are, and that’s exactly what you’ll find in this collection of elegant vacation dresses. Whether you’re drawn to the timeless allure of a classic maxi or the head-turning sparkle of a gold vacation dress, each piece is designed to help you own every moment with confidence. And if you’re on the hunt for even more inspo to fill your travel wardrobe with that main character energy, check out our curated picks on Summer Dresses For Vacation—because unforgettable vacations call for unforgettable style.