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.
$36.90
An elegant sage off-the-shoulder midi dress with a bodycon fit and flared hem.
$54.90
A stunning mauve satin gown with a cowl neck, high slit, and sleek spaghetti straps.
$44.90
A sophisticated white midi dress featuring chiffon sleeves, a square neckline, and a ruched bodycon silhouette.
$46.90
A vibrant yellow skater dress with a ruffled skirt and halter tie-back straps for sunset outings.
$109.90
A black sequin bodycon dress with a high slit, adjustable straps, and padded bust for formal events.
$45.90
An elegant white satin midi dress with a strapless cowl neckline and form-hugging fit.
$19.97 $79.90 75% off
A burgundy formal dress with faux pearl embroidery, sweetheart neckline, and high slit mermaid silhouette.
$69.90
A green satin midi dress with a lace-up back and faux wrap bodycon silhouette.
$69.90
A blue floral crepe mermaid dress with a sweetheart neckline and high front slit.
$44.90
A gold metallic knit maxi dress featuring a plunge cowl halter neckline and adjustable strappy open back.
$19.97 $59.90 67% off
A white crepe formal dress featuring adjustable straps, ruffle trim, and a dramatic high front slit.
$149.90
A peach column dress with sequin beaded mesh, adjustable straps, and a high side slit.
$59.90
An ivory A-line maxi dress featuring gauze fabric, sheer lace insets, and a faux leather belt.
$20.97 $46.90 55% off
An abstract red knit maxi dress featuring a cowl neckline, hoop trims, strappy back, and high side slit.
$49.90
A burgundy mesh maxi dress featuring a floral print, plunge halter neckline, and mermaid silhouette.
$64.90
A wine velvet mermaid dress with a chic ruched halter neckline and partially open back.
$79.90
A glamorous black glitter knit mermaid dress with a ruched wrap-front and high slit.
$34.90
A chic brown strapless maxi dress with a high slit and flattering bodycon silhouette.
$44.90
A sultry black floral maxi dress with a V-neckline and form-hugging silhouette, perfect for vacations.
$9.97 $49.90 80% off
An elegant black mesh midi dress with ruched details, sheer sleeves, and a ruffled hem.
$59.90
A white satin wrap midi dress with a sleeveless cowl neckline and high-side slit.
$19.97 $69.90 71% off
An elegant black mermaid dress with a glitter knit fabric and pleated cowl neck overlay.
$39.90
A strapless black floral maxi dress crafted from mesh and knit fabric with a high side slit.
$49.90
A brown mesh maxi dress featuring a bold floral print, drapey cowl halter neckline, and curve-hugging fit.
$19.97 $64.90 69% off
A black knit mermaid dress with an off-the-shoulder neckline and ruched bodice for formal occasions.
$19.97 $39.90 50% off
A natural paisley-print maxi dress in mesh with a bodycon fit, square neckline, and high side slit.
$34.90
A chic wine maxi dress with a strapless neckline, high slit, and form-hugging knit fabric.
$56.90
A black velvet skater dress with a strapless neckline and pleated mini-length hem for elegant occasions.
$19.97 $34.90 43% off
A light blue floral mesh maxi dress featuring a strapless neckline and curve-hugging, elegant silhouette.
$59.90
A navy blue satin midi dress with a V-neckline, strappy back, and side slit.
$44.90
A strapless burgundy mesh maxi dress featuring a bold floral print and a high side slit.
$39.90
A brown tropical floral mesh midi dress featuring a strapless neckline, ruched sides, and flowy sheer hem.
$109.90
A chic navy blue mermaid dress with sequins, a square neckline, and a thigh-high slit.
$36.90
A denim satin mini dress with a ruched wrap silhouette and sleeveless square neckline.
$69.90
A wine-colored formal dress with a glitter mesh fabric, cowl neckline, and floor-length silhouette.
$49.90
A black crepe formal dress featuring a sleeveless square neckline and a high-cut front slit.
$52.90
A white mini bodycon dress with faux pearl embellishments, featuring a sweetheart neckline and ruched seams.
$19.97 $39.90 50% off
A chic white glitter lace dress with a bodycon fit, adjustable straps, and asymmetric hem.
$77 $109.90 30% off
A green sequin scroll dress with a plunging V-neckline and open lace-up back.
$46 $64.90 29% off
A black crepe formal dress with puff sleeves, lace-up back, and high-cut slit for prom.
$149.90
A luxurious pink mesh formal dress with faux pearl beading, cowl neckline, and high front slit.
$40.90
A black glitter mini dress with a halter cowl neckline and tie-back spaghetti straps.
$89.90
A black knit mermaid dress featuring an off-the-shoulder neckline and dramatic high front slit.
$69.90
A taupe satin strapless mermaid dress with a sweetheart neckline and chic pleated detailing.
$19.97 $69.90 71% off
A lavender mesh off-the-shoulder dress with ruched seams and a mermaid silhouette for formal events.
$59.90
A glamorous black bodycon dress with glitter knit fabric, off-the-shoulder neckline, and high slit.
$59.90
A sleek eggplant column dress with a cutout accent and high side slit for sultry allure.
$74.90
An exquisite mauve mermaid dress with a glitter knit fabric and off-the-shoulder sweetheart neckline.
Now Trending
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-2 | Size: S | Rhinestone/Velvet Fabric
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 Red | Size: XS | Knit Fabric/Satin Fabric
Sophistication meets sultry on the Marjorie formal dress perfect for cocktail parties and dressy family get-togethers. She features sheer chiffon peasant long sleeves, a square neckline, a bodycon silhouette, and a front ruched seam leading to the skin-flaunting slit along her midi-length hem. The formal dress is composed of a lined crepe fabric with a moderate stretch. Style with a chic clutch and heels to complete the look! Fit & FeaturesSheer chiffon peasant long sleeves, square neckline, Front ruched seam, slit detail, Bodycon silhouette, Midi-length hem, Lined crepe fabric, moderate stretch, Bra-friendly design, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Marjorie Formal Chiffon Sleeve Midi Dress in White | Size: S | Chiffon/Crepe Fabric
A chic staple skater dress featuring a flirty off-the-shoulder folded neckline and a short-length perfect for styling with boots or heels. Fit & FeaturesRibbed knit fabric with plenty of stretch, Off-the-shoulder neckline, fold-over accent, Long fitted sleeves, Short-length hem, Skater silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Staple Ribbed Knit Skater Dress in Black | Size: M | Knit Fabric
The Gwendolyn glitter knit bow-back mermaid dress will have you sparkling up the night with a glamorous allure! Make your entrance in this floor-length gown designed to turn heads with a curve-flaunting mermaid fit and backless design. Fit & FeaturesGlitter knit fabric, moderate stretch, Square neckline, spaghetti straps, Backless design, high waist seam, Bow-back accent, floor-length train, Floor-sweeping hem, mermaid silhouette, Runs true to size, Extra glitter for maximum sparkle - may have some natural fallout, Where to Wear:Weddings, black tie galas, formal dances, big birthday events, rehearsal dinners, engagement parties, red carpet occasions, upscale glam parties Free Shipping on All Orders Over $75. | Windsor Gwendolyn Glitter Knit Bow-Back Mermaid Dress in Black | Size: L | Knit Fabric
A sparkling sequin scroll pattern adds beauty and shine to the glamorous Saige formal long dress! With a lace-up back that turns heads, a curve-hugging mermaid silhouette, and a high slit for a gorgeous look. Fit & FeaturesSequin scroll pattern, mesh fabric, stretchy full knit lining, Sleeveless plunge V-neckline, padded bust, Spaghetti straps, open lace-up back detail, Back zipper and hook-eye closure, Mermaid silhouette, floor-length hem, Runs true to size, Where to Wear:Prom, black-tie events, glam functions, and parties. Free Shipping on All Orders Over $75. | Windsor Saige Formal Sequin Lace-Up Mermaid Dress in Lavender | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
The Lucille formal satin dress will have you looking and feeling radiant and luxe! The dress captivates with a lace-up back, mermaid silhouette, and high front slit for effortless allure. Fit & FeaturesLined satin knit fabric, minimal stretch, Sleeveless square neckline, padded bust, adjustable spaghetti straps, Open lace-up back design, zipper and hook-eye closure, Fitted bodice, front ruched seam, high-cut slit, Mermaid silhouette, floor-length hem, Runs true to size, Where to Wear:Prom, weddings, bridesmaids, black tie galas, red-carpet events, nights at the opera or theatre, big milestone celebrations Free Shipping on All Orders Over $75. | Windsor Lucille Formal Satin Mermaid Dress in Coral | Size: L | Knit Fabric/Satin Fabric
Bring the romantic allure to the evening affair in the Marylou lace mesh plunge formal dress! She embodies flirtatious style in a sleeveless plunge V-neckline with a built-in padded bust and adjustable spaghetti straps on her empire waist bodice. The sparkly embroidered lace mesh fabric effortlessly flows into a floor-length silhouette with a high-side slit to showcase some legs. She also features a curve-conscious silhouette to flaunt your stunning figure! Complete the look in an elegant hair clip. Fit & FeaturesPlunge V-neckline, adjustable spaghetti straps, Adhesive bra recommended, built-in padded bust, High side slit, back zipper, hook and eye closure, Empire waist, form-fitting silhouette, Floor-length hem, Sparkly embroidered lace mesh fabric, full knit lining, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Marylou Lace Mesh Plunge Neck Formal Dress in Black | Size: L | Knit Fabric/Mesh Fabric/Mesh Fabric
Spend an evening in the timeless elegance of the Alicia floor-length formal dress and feel like a work of art! The side ruched seams accentuate your curves along the mermaid silhouette, and the high front slit adds a touch of drama to the floor-length hem. Fit & FeaturesSmooth knit fabric lined with stretchy knit, Padded bra cups, Back zipper and hook-eye closure, High front slit, Mermaid silhouette, Runs true to size, Where to Wear:Prom, galas, black tie parties, weddings, bridesmaids, nights at the theatre and opera, red-carpets Free Shipping on All Orders Over $75. | Windsor Alicia Off-The-Shoulder Mermaid Formal Dress in Green | Size: XS | Knit Fabric
Sleek and sophisticated! The Emmie satin formal dress exudes elegance with a lace-up back and flattering mermaid silhouette that accentuates your figure. Fit & FeaturesStretchy satin-knit fabric, lined bust, Spaghetti straps, V-neckline, Lace-up back, Mermaid silhouette, floor-length hem, Runs true to size, Where to Wear:Prom, black-tie galas, weddings, bridesmaids, formal parties, and red-carpet events. Free Shipping on All Orders Over $75. | Windsor Emmie Lace-Up Mermaid Satin Formal Dress in Brown | Size: L | Satin 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.