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.

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Windsor Blooming Beauty Floral Print Mesh Maxi Dress in Red

$44.90

A red floral print mesh maxi dress with a sleeveless sweetheart neckline and bodycon silhouette.

Glow Goddess Strappy Back Metallic Knit Maxi Dress in Gold

$44.90

A shimmering gold metallic knit maxi dress with a plunge cowl halter neckline and strappy open back.

Windsor Drama Meets Paradise Floral Maxi Dress in Brown

$46.90

A brown floral mesh maxi dress featuring a plunging cowl neckline and strappy open back.

Jianna Floral Satin Short A-Line Dress in Ivory

$54.90

An ivory floral satin dress with a lace-up back and flirty A-line silhouette.

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Mayra Formal Satin Slit Long Dress in Navy Blue-2

$59.90

(182)

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

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Addison Glitter Mesh Formal Dress in Black

$29.97 $69.90
57% off

(116)

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

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

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 Jamie Lace-Up Satin Formal Column Dress in Brown

$89.90

(72)

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

Shayla Strapless Corset Lace Formal Dress in Red

$159.90

(70)

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

Womens Tropical Vacation Dresses

There’s something about slipping into a tropical vacation dress that instantly transports you from winter’s chill to sun-drenched shores, even if your flight is still a few weeks away (or you’re just daydreaming at your desk). January might have you bundled up in layers, but this is exactly when the promise of palm trees, ocean breezes, and a suitcase full of breezy, beautiful dresses feels most tempting. Whether you’re planning a quick escape to the islands, booking a last-minute cruise, or just manifesting warmer days ahead, the right dress does more than fill space in your luggage—it sets the vibe for your entire getaway. Think of it as your passport to effortless style: lightweight fabrics that move with you, bold prints that make every snap Instagram-worthy, and silhouettes that go from poolside lounging to sunset dinners without missing a beat. Windsor vacation dresses are designed to make packing easy and getting dressed even easier, so you can focus on chasing the sun, not stressing over what to wear. And let’s be honest, there’s a certain magic in pulling a satin vacation dress from your closet and feeling instantly ready for whatever adventure (or cocktail) comes your way.

If you’re gifting, tropical vacation dresses are a thoughtful pick for anyone with a trip on the horizon—a sister celebrating graduation, your best friend’s birthday, or that cousin who’s always planning her next escape. They’re the kind of present that says, “I see you, and I know you’re about to live your best life.” When choosing for yourself or someone else, it’s all about versatility and comfort. Look for details like adjustable straps, smocked backs, or flowy skirts that keep things easy-breezy, even when the humidity rises. Maxi lengths channel that effortless island goddess energy (the windsor island muse floral maxi dress brown is a perennial favorite for a reason), while mini and midi cuts bring playful energy to beachside brunches or city strolls. Prints are your best friend here—think lush botanicals, dreamy sunsets, and anything that feels like it belongs under a cabana. And don’t underestimate the power of a neutral—sand, ivory, and cocoa tones are as timeless as they are flattering, especially when paired with sun-kissed skin and tousled hair. For those who crave a little extra drama, the windsor sun and moon dress brings celestial charm to balmy evenings and rooftop dinners, proving that vacation style can be both relaxed and unforgettable.

Packing for a tropical getaway is about striking the right balance between comfort, confidence, and that little thrill you get from wearing something new. Prioritize fabrics that breathe—cotton, linen, and lightweight satins keep you cool and comfortable from sunrise to starry nights. A satin vacation dress, for example, offers that perfect blend of laid-back luxury and easy maintenance (because nobody wants to spend vacation ironing). Don’t forget the practical touches: pockets for your essentials, adjustable features for a custom fit, and styles that layer well with swimsuits or lightweight jackets for those breezy evenings. The beauty of a well-chosen vacation dress is its ability to play multiple roles—throw it over your bikini for a beach bar lunch, then add a strappy sandal and statement earrings for dinner by the water. If you’re building your own packing list or looking for more inspiration, explore our curated collection of Tropical Dresses to find styles that feel as good as they look. Wherever your travels take you—whether it’s a far-flung island or a rooftop with a view—your wardrobe should celebrate the moment. After all, the best vacation memories always start with the perfect dress.

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