Casual Vacation Dresses
Jet-setting off to a dreamy destination or planning a spontaneous weekend getaway? Our collection of casual vacation dresses has got your back, ready to make every moment feel like a sun-kissed adventure. Think breezy fabrics, vibrant colors, and effortlessly chic styles that scream "vacay mode activated!" Whether you're strolling through cobblestone streets or lounging by the beach, these dresses are your ultimate travel buddies, keeping you stylishly cool and confidently carefree. So go ahead, pack your bags and slip into something fabulous—your next unforgettable escape awaits!
$36.90
An elegant off-the-shoulder natural knit midi dress with a bodycon fit and flared hem.
$48.90
A breezy white eyelet knit mini skater dress with a flirty tie-back and ruffled hem.
$20.97 $46.90 55% off
An abstract red knit maxi dress featuring a cowl neckline, hoop trims, strappy back, and high side slit.
$32.90
A breezy white eyelet knit skater dress featuring a square neckline and double-layered flared skirt.
$44.90
A gold metallic knit maxi dress featuring a plunge cowl halter neckline and adjustable strappy open back.
$9.97 $46.90 79% off
A blue gauze skater dress featuring a halter neckline, cutout bodice, and ruffled mini hem.
$59.90
An ivory A-line maxi dress featuring gauze fabric, sheer lace insets, and a faux leather belt.
$42.90
A navy blue paisley skater dress with a halter V-neckline and playful tie-back design.
$9.97 $42.90 77% off
A slate A-line mini dress with a V-neckline and ruffled hem in soft knit fabric.
$54.90
A denim woven maxi dress featuring a flowy ruffled silhouette, square neckline, and spaghetti straps.
$9.97 $49.90 80% off
A strapless ivory skater dress with a floral print and flirty ruffled hem.
$34.90
A chic brown strapless maxi dress with a high slit and flattering bodycon silhouette.
$19.97 $39.90 50% off
A natural paisley-print maxi dress in mesh with a bodycon fit, square neckline, and high side slit.
$44.90
A sultry black floral maxi dress with a V-neckline and form-hugging silhouette, perfect for vacations.
$44.90
A taupe paisley skater dress with a halter V-neck and stretchy smocked bodice.
$49.90
A brown mesh maxi dress featuring a bold floral print, drapey cowl halter neckline, and curve-hugging fit.
$20.97 $46.90 55% off
An olive green gauze skater dress featuring flowy sleeves, V-necklines, and a chic cutout bodice.
$9.97 $37.90 74% off
An ivory floral bodycon mini dress featuring a strapless neckline and flirty ruffled hem.
$9.97 $49.90 80% off
A strapless black woven midi dress featuring a color block bodice, flowy hem, and hidden pockets.
$26.90
A taupe plaid mini dress with a V-neckline, spaghetti straps, and a bodycon silhouette.
$39.90
A brown tropical floral mesh midi dress featuring a strapless neckline, ruched sides, and flowy sheer hem.
$25 $34.90 28% off
A grey plaid strapless mini dress with a pleated hem and form-hugging knit fabric.
$32.90
An ivory striped ribbed knit mini dress with an off-the-shoulder neckline and long fitted sleeves.
$36.90
A denim satin mini dress with a ruched wrap silhouette and sleeveless square neckline.
$46.90
A brown woven midi dress with a ditsy floral pattern, corset bodice, and high front slit.
$68.90
An ivory satin skater dress with floral jacquard, corset bodice, and lace-up back for chic elegance.
$44.90
A red floral print mesh maxi dress with a sleeveless sweetheart neckline and lace trim.
$44.90
A green glitter knit mini dress with a pleated cowl neckline and asymmetric wrap-front design.
$35.90
A pink sleeveless bodycon midi dress with a square neckline and stretchy knit fabric.
$49.90
A lavender skater dress with glitter mesh, sheer sleeves, and a fit and flare silhouette.
$39.90
A sheer white crochet knit cover-up dress with long sleeves, plunge neckline, and chic hoop insert.
$38.90
A vibrant pink mini dress featuring a leopard snake print, mesh fabric, side cutout, and ruffled slit.
$21.97 $42.90 49% off
An effortlessly chic brown ribbed knit mini dress with long sleeves and a scoop neckline.
$29.90
Occasions made easy! This strapless lace mini dress is here to make you stand out at brunch or parties with a twirl-worthy hanky hem. Fit & FeaturesLace fabric lined with stretchy knit, Strapless neckline, Side ruched seams, fitted bodice, Flared hanky mini length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Going Out Strapless Lace Mini Dress in Brown | Size: L | Lace Fabric
$42.90
An abstract print maxi dress with a ruched bodycon silhouette and sheer off-the-shoulder sleeves.
$36.90
A cozy heather grey ribbed knit mini dress with an off-the-shoulder neckline and A-line silhouette.
$39.90
An ivory lace skater dress with an off-the-shoulder neckline and sheer long fitted sleeves.
$44.90
A natural-colored knit mini dress with an off-the-shoulder neckline and twist popover accent.
$29.90
A trendy brown striped knit mini dress with a mock neckline and long fitted sleeves.
$44.90
A green mini dress with a sleeveless square neckline, cap-like sleeves, and flattering ruching.
$9.97 $56.90 82% off
A floral chiffon romper in natural with a strapless neckline and flattering drop waist seam.
$6.97 $29.90 77% off
A taupe ribbed knit bodycon mini dress with a scoop neckline and spaghetti straps.
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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 Sage | Size: S | Satin Fabric
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
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
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
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
Make a sparkly statement at your next soiree in the trendy glam Addison glitter formal dress! Bring radiance to the room in this floor-length dress with a sleek design that fits like a glove. Fit & FeaturesSheer glitter mesh fabric, full knit stretchy lining, Sleeveless cowl neckline, spaghetti straps, High waist seam, Floor-length fitted silhouette, Runs true to size, Where to Wear:Prom, black tie weddings, galas, special date nights, rehearsal dinner Free Shipping on All Orders Over $75. | Windsor Addison Glitter Mesh Formal Dress in Black | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
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:Prom, black-tie events, formal weddings, and upscale parties. Free Shipping on All Orders Over $75. | Windsor Bethanie Formal Sequin V-Neck Mermaid Dress in Yellow | Size: S | Knit Fabric/Mesh Fabric/Mesh Fabric
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 Black | Size: L | Stretchy Fabric/Rhinestone
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
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 Green | Size: M | Knit Fabric/Mesh Fabric
Casual Vacation Dresses
Ready to live your best life, suitcase in one hand and iced coffee in the other? Let’s talk about the magic of casual vacation dresses—the ultimate sidekick for every getaway, from spontaneous road trips to that long-awaited island escape. Picture this: you, stepping off the plane or out of the car, feeling fresh, flirty, and totally unbothered by wrinkly, fussy outfits. That’s the energy a windsor casual dress brings to your vacay wardrobe. These dresses are all about effortless style and comfort, letting you slay the day from sunrise mimosas to late-night beach strolls. They’re the kind of pieces you can toss in your bag and forget about until you’re ready to throw one on and instantly look put together—no steamer, no stress, just pure confidence. Whether you’re snapping pics for the ‘gram, exploring cute local spots, or just vibing poolside with your crew, a casual vacation dress is your golden ticket to looking and feeling like the main character, every single day.
Gifting a casual vacation dress? Major bestie points incoming. These dresses are the ultimate “thinking of you” present for your ride-or-die, your sister, or that friend who’s always booking her next adventure. They’re the answer for birthdays, bachelorette trips, or just because—you know she’ll wear it on repeat. And let’s be real: nothing says “I love you” like giving someone the power to pack light and still look fire. When you’re choosing the perfect windsor casual dress, think about what makes her feel unstoppable. Flowy silhouettes that catch the breeze, playful prints that match her energy, and soft, breathable fabrics that keep her cool while she’s out chasing sunsets. Dresses with adjustable straps, smocked bodices, or tie waists are always a win—they flex with her style, whether she’s craving a laid-back look or ready to spice things up for dinner in a new city.
If you’re all about collecting memories (and compliments), these dresses are a must. They’re made for mixing and matching with everything from sneakers and sandals to statement jewelry and oversized sunnies. And when you’ve got a closet full of casual vacation dresses, outfit planning is basically a non-issue. Just grab your favorite, slip it on, and you’re ready for whatever adventure comes your way. No more overthinking, no more “I have nothing to wear” panic—just pure, carefree vibes. If you’re feeling inspired to level up your getaway wardrobe, or searching for the perfect gift that’ll leave her speechless, check out our curated collection of Women's Vacation Dresses. Your next iconic look is waiting, and trust us, you’re about to make every moment unforgettable.