Womens Tropical Vacation Dresses
Sunshine, palm trees, and a lineup of women’s tropical vacation dresses that are basically a one-way ticket to paradise—yes, please! Whether you’re chasing sunsets or dancing the night away under swaying palms, these dreamy dresses were made for making memories (and turning heads) in every corner of your getaway. Let your style do the talking while you soak up those carefree vibes—because you deserve to look as bold and unforgettable as your adventure.
$19.97 $44.90 56% off
A black one-shoulder tropical maxi dress with a ruffled slit and metal-accented strap.
$49.90
A brown mesh maxi dress featuring a bold floral print, cowl halter neckline, and curve-hugging fit.
$49.90
A brown mesh maxi dress featuring a tropical floral print, strappy open back, and form-hugging fit.
$46.90
A brown floral mesh maxi dress featuring a plunging cowl neckline and strappy open back.
$54.90
An olive green woven jumpsuit featuring a halter neckline, cutout bodice, and ruffled wide-leg silhouette.
$44.90
A gold metallic knit maxi dress featuring a plunge cowl halter neckline and adjustable strappy open back.
$44.90
A sultry black floral maxi dress with a V-neckline and form-hugging silhouette, perfect for vacations.
$19.97 $39.90 50% off
A natural paisley-print maxi dress in mesh with a bodycon fit, square neckline, and high side slit.
$19.97 $42.90 53% off
A royal blue maxi dress featuring a tropical print, lace-up back, stretchy knit fabric, and high slit.
$20.97 $46.90 55% off
A sage green mini dress featuring a halter neckline, ruffled skater silhouette, and airy woven fabric.
$39.90
A brown tropical floral mesh midi dress featuring a strapless neckline, ruched sides, and flowy sheer hem.
$42.90
A strapless black floral maxi dress featuring mesh-lined fabric, a curve-hugging fit, and a high side slit.
$54.90
An ivory floral satin dress with a lace-up back and flirty A-line silhouette.
$46.90
A chic black knit jumpsuit featuring a strapless neckline and flattering wide-leg silhouette.
$19.97 $46.90 57% off
A rust-colored tropical print jumpsuit featuring a deep V-neckline, tie-back halter straps, and wide-leg silhouette.
$79.90
A purple floral mesh mermaid dress featuring a cowl neckline, lace-up back, and high front slit.
$44.90
A brown tropical print knit jumpsuit featuring a halter neckline, cutout bodice, and wide-leg silhouette.
$54.90
A black and white tropical print jumpsuit featuring a halter cowl neckline and flowy wide-leg silhouette.
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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 Black | Size: M | Knit Fabric
Channel the chic fall vibe in this ditsy floral woven midi dress featuring a sleeveless sweetheart neckline with a ruched bust and tie-front detail, thin tank shoulder straps, and a corset-style bodice. The high waist leads to a flowy A-line silhouette accented with a high-cut front slit. Fit & FeaturesDitsy floral-printed woven fabric, Sweetheart neckline, ruched bust, tie-front detail, underwire bust, Thin tank shoulder straps, Corset-style bodice with piping, high waist seam, Hidden side zipper and hook-eye closure, High front slit, Midi-length A-line fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Fall Vibe Ditsy Floral Corset Midi Dress in Brown | Size: S | Woven Fabric
Windsor Thriving Blooms Corset Floral Slit Midi Dress in Black
$20.97 $46.90
55% off
Thrive with sweet energy in this floral midi dress perfect for brunches or dates! With a corset bodice that snatches your waist and a flirty front slit, this a-line dress will captive everyone. Pair with a necklace. Fit & FeaturesDitsy floral print, woven fabric, Wide shoulder straps, sweetheart neckline, Corset bodice, Side pockets, A-line silhouette, front slit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Thriving Blooms Corset Floral Slit Midi Dress in Black | Size: M | Woven Fabric
Capture hearts with your sweet look in this airy eyelet knit skater dress. You'll adore the flowy feel of the fit-and-flare silhouette. Fit & FeaturesEyelet knit fabric with knit lining, Sleeveless square neckline, underbust seam, Adjustable spaghetti straps, Skater silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Look Eyelet Knit Skater Dress in White | Size: M | Knit Fabric
Create a cute picturesque 'fit in this corset A-line midi dress! The corset bodice and lace-up back add a touch of allure to the sweet silhouette. Fit & FeaturesWoven fabric lined with stretchy knit, Sweetheart neckline, tie-front detail, Thin adjustable straps, Corset bodice, lace-up back, High waist seam, Midi-length A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Picturesque Cutie Corset Lace-Up A-Line Midi Dress in Light Blue | Size: L | Woven Fabric
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 Light Blue | Size: L | Knit Fabric
This sleeveless ribbed knit midi dress features a striking V-neckline and bodycon fit with a front slit detail for movement. Perfect for layering with a jacket and heels. Fit & FeaturesStretchy ribbed knit fabric, V-neckline, Spaghetti straps, Front slit, Midi-length bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Toasty Sweetheart V-Neck Bodycon Knit Midi Dress in Chartreuse | Size: L | Knit Fabric
The perfect chic sleeveless midi dress for grabbing dinner downtown! Crafted from smooth knit fabric, this crew neck dress boasts curve-accentuating ruched seams along the bodycon silhouette and a sleek midi-length hem. Pair with kitten heels and a clutch. Fit & FeaturesSmooth knit fabric, stretchy knit lining, Sleeveless crew neck, Side ruched seams, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Dinner Downtown Sleeveless Ruched Midi Dress in Brown | Size: S | Knit Fabric
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: L | Knit Fabric
Windsor Petit Blooms Floral Eyelet Midi Dress in Ivory
$9.97 $30.90
68% off
Dainty floral makes this eyelet midi dress the cutest spring-to-summer style! Fit & FeaturesDainty floral print, eyelet fabric, sewn-in knit lining, Strapless neckline, Bodycon fit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Petit Blooms Floral Eyelet Midi Dress in Ivory | Size: XS | Knit Fabric
Womens Tropical Vacation Dresses
Ready to channel your main character energy? Tropical vacation dresses are basically your passport to paradise, whether you’re hopping a flight to a dreamy island or just manifesting that getaway vibe at your next pool party. These dresses are made for the girls who crave adventure, who want to feel the sun on their skin and the breeze in their hair, and who never shy away from a little drama—in the best way possible. Think flowy fabrics that catch the light, bold prints that pop against turquoise water, and silhouettes that let you twirl from sunrise mimosas to late-night beach bonfires. The right tropical dress doesn’t just look cute in pics (though, let’s be real, you’ll be serving looks for the ‘gram)—it’s also about feeling confident, comfortable, and totally free. When you’re packing for that once-in-a-lifetime trip or just want to bring a touch of vacay to your everyday, go for styles that are lightweight and easy to layer, with details like flirty cutouts, tie-backs, and adjustable straps. Trust, you’ll thank yourself when you’re breezing through airport security or dancing barefoot in the sand.
A tropical vacation dress is the ultimate BFF for girls’ trips, honeymoons, or even a solo adventure that’s all about self-love. They make the perfect gift for your bestie who just booked her dream escape, or for that family member who’s always planning the next getaway. These dresses are the secret weapon for destination weddings, cruises, and every “wish you were here” moment in between. When you’re picking the perfect dress, think about where you’ll be living your best life—flowy maxis and breezy midis are a vibe for sunset dinners, while playful minis bring all the energy for poolside hangs or exploring local markets. Don’t be afraid to go bold with tropical florals, palm prints, or juicy colors that look amazing with a fresh tan and your favorite statement earrings. And because we know you’re not about that high-maintenance life, look for easy-care fabrics that pack like a dream (wrinkle-resistant = more time for fun, less time ironing). Whether you’re snapping selfies on a rooftop bar, twirling under fairy lights, or just soaking in the good vibes, tropical vacation dresses are your ticket to feeling like the main character no matter where you are. For even more inspo and to find your next go-to look, check out our curated collection of Tropical Beach Dresses—because paradise is a state of mind, and you deserve to dress like it.