Island Maxi Dresses

Sashay into paradise vibes with our collection of island maxi dresses, where every piece is your passport to sun-kissed adventures and breezy elegance. Whether you're planning a dreamy getaway or just want to channel those tropical feels right at home, these dresses are your ultimate style companions. Think flowy silhouettes that dance with the ocean breeze and vibrant prints that make you feel like the queen of your own island. Perfect for lazy beach days or sizzling sunset soirées, these island maxi dresses will have you living your best life—no plane ticket required!

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Windsor Island Muse Floral Maxi Dress in Brown

$19.97 $49.90 60% off

A brown mesh maxi dress featuring a bold floral print, cowl halter neckline, and curve-hugging fit.

Blooming Beauty Floral Print Mesh Maxi Dress in Red

$44.90

A red floral print mesh maxi dress with a sleeveless sweetheart neckline and lace trim.

Glow Goddess Strappy Back Metallic Knit Maxi Dress in Gold

$44.90

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

Laid Back Fave Crew Neck Tank Maxi Dress in Black

$34.90

A black rib-knit maxi dress featuring a crew neck and form-hugging, stretchy silhouette for versatile styling.

Windsor Little Bit Of Drama Low Back Maxi Dress in Olive

$38.90

An olive green maxi dress featuring a low back with tie, cowl neckline, and stretchy knit fabric.

Love in Full Bloom Floral Maxi Dress in Brown

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Love in Full Bloom Floral Maxi Dress in Brown

$19.97 $59.90 67% off

A brown woven floral maxi dress with flutter sleeves, open back, and a draped, fitted A-line silhouette.

Serve Sultry Vibes Halter Cowl Neck Maxi Dress in Brown

$44.90

A sleek brown knit maxi dress with a halter cowl neckline and alluring open back.

Windsor Sleek Fit Strapless High Slit Maxi Dress in Wine

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Windsor Sleek Fit Strapless High Slit Maxi Dress in Wine

$19.97 $34.90 43% off

A chic wine maxi dress with a strapless neckline, high slit, and form-hugging knit fabric.

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Windsor Mayra Formal Satin Slit Long Dress in Sage

$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 Sage | Size: S | Satin Fabric

Marissa Formal Satin Cowl Neck Dress in Green

$89.90

(179)

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: XS | 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-2

$59.90

(129)

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

Addison Glitter Mesh Formal Dress in Black

$69.90

(114)

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

Amirah Formal Glitter Cowl Neck Column Dress in Black

$59.90

(74)

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 Black | Size: XS | Knit Fabric

Windsor Jamie Lace-Up Satin Formal Column Dress in Red

$89.90

(71)

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

Rose Formal Mesh Corset Column Dress in Brown

$54.90

(71)

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 Savannah Formal Crepe Long Dress in Black

$49.90

(66)

Stunning for brides and celebrations, the Savannah formal crepe dress showcases simplicity and chicness! With a form-hugging silhouette and sultry high front slit, this formal dress is perfect for an evening of elegance. Fit & FeaturesLined crepe fabric, moderate stretch, Sleeveless square neckline, tank-style straps, Back zipper and hook-eye closure, Form-hugging silhouette, Front high-cut slit, Floor-length hem, Runs true to size, Where to Wear:Prom, weddings, bridesmaids, red-carpet events, milestone celebrations Free Shipping on All Orders Over $75. | Windsor Savannah Formal Crepe Long Dress in Black | Size: XS

Island Maxi Dresses

There’s something about slipping into an island maxi dress that instantly transports you—even if your toes are just digging into the living room rug and not the sand. These dresses are more than a vacation staple; they’re a mindset. Picture this: you’re packing for a winter getaway, or maybe you’re just dreaming of one while the world outside is cold and gray. An island dress is your ticket to that breezy, sun-drenched feeling, no matter the forecast. Think sweeping silhouettes that catch the wind, bold prints that pop against any backdrop, and lightweight fabrics that move with you from brunch to beach bonfire. Island vibe dresses have this effortless way of making you feel dressed up and laid-back at the same time—no overthinking required. They’re the kind of pieces you reach for when you want to look like you didn’t try too hard, but still want to turn heads (and maybe spark a little outfit envy on the group chat).

Island dresses aren’t just for the jet set or the lucky few headed somewhere warm this season. They’re for anyone craving a little escape, even if it’s just in spirit. Maybe you’re hosting a holiday dinner with a tropical twist, planning a destination wedding, or searching for a gift that feels like a getaway in garment form. Island maxi dresses make thoughtful presents—imagine the look on her face when she unwraps a dress that promises balmy evenings and carefree adventures, right in the middle of December. And if you’re the one shopping for yourself, consider how these dresses flex to fit your plans. They’re the answer to “what do I wear?” for everything from casual coffee runs to formal island events, thanks to details like adjustable straps, smocked waists, and flowy skirts that flatter every figure. If you’re heading somewhere special, formal island dresses deliver that elevated vibe without sacrificing comfort—think island formal wear that’s as easy to dance in as it is to lounge by the water. The beauty of these dresses is in their versatility: add sandals and a sunhat for day, swap in strappy heels and statement earrings for night, and suddenly you’re ready for anything the itinerary (or your imagination) throws your way.

When you’re shopping for island dresses, keep an eye out for those little details that make a big difference—breathable fabrics that hold up in the heat, adjustable ties for a custom fit, and prints that make you feel like you’re on holiday, even if you’re just running errands. Don’t be afraid to play with color and silhouette; after all, island vibe dresses are about celebrating your mood and making every day feel a little more like a getaway. Whether you’re curating your own closet or searching for the perfect gift, these dresses are designed to bring a sense of joy and wanderlust to any occasion. And if you’re looking to expand your collection or explore more ways to wear the maxi trend, you’ll find even more inspiration (and plenty of swoon-worthy options) on our Modern Maxi Dresses page. Island or not, your next adventure in style starts here.

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