Stretchy Maxi Dresses

Stretchy maxi dresses are your new go-to for effortless style and comfort, perfect for any occasion where you want to look fabulous without sacrificing ease. These beauties flow with your every move, making them the ultimate wardrobe staple for our Windsor girl who's always on the go. Whether you're hitting up brunch with the squad or dancing the night away, these dresses have got you covered from head to toe. Slip into one and let your inner goddess shine—because when it comes to turning heads, you're already a pro.

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Windsor Serve Sultry Vibes Halter Cowl Neck Maxi Dress in Brown

$44.90

A sultry brown maxi dress with a halter cowl neck and curve-hugging mermaid silhouette.

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 Ruffle and Ready Chiffon Halter Maxi Dress in Brown

$59.90

A brown chiffon maxi dress featuring cascading ruffles, sultry cutouts, and a flowy front slit.

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.

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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.

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.

Windsor Born to Be Bold Lace Leopard Maxi Dress in Brown

$49.90

A sultry brown leopard-print maxi dress featuring sheer mesh, lace details, and daring high side slits.

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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

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 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

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

Windsor Shayla Strapless Corset Lace Formal Dress in Black

$159.90

(64)

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 Black | Size: S | Knit Fabric/Sheer Mesh Fabric

Stretchy Maxi Dresses

Let’s talk about the real MVP of your closet: the stretchy maxi dress. If you’ve ever spent twenty minutes in front of your closet, silently negotiating with yourself over comfort versus style, you already know the magic of a dress that does both. Maxi stretch dresses are the ultimate answer to “I want to look put together, but I also want to breathe—and maybe eat dessert.” The beauty of a stretchy maxi dress is all in the details: soft, forgiving fabrics that move with you, lengths that sweep the floor with just the right amount of drama, and silhouettes that flatter without feeling fussy. Whether you’re headed to a holiday dinner, a friend’s birthday brunch, or just running errands with a coffee in hand, a stretch dress has you covered (literally and figuratively). The best part? You don’t have to compromise. These dresses with stretch fabric are designed to flex with your plans, your mood, and yes, even your body as it changes through the seasons.

December is the season of layering, last-minute invites, and endless reasons to dress up (or down). A stretchy dress is your not-so-secret weapon for all of it. Picture this: you’re racing from work to a winter gathering, and you need something that transitions as easily as you do. Slip into a maxi stretch dress with a cozy cardigan and boots for daytime, then swap in a bold lip and statement earrings for evening. Suddenly, you’re the best-dressed person in the room—and you didn’t have to change twice. For those who love gifting, stretchy maxi dresses make a thoughtful present for anyone who values both comfort and style. They’re a win for your sister who’s always on the go, your best friend who loves a good twirl moment, or even yourself (because self-gifting is absolutely a thing). And let’s be honest: nothing says “I get you” like a dress that’s as adaptable as she is.

When shopping for your next wardrobe hero, pay attention to the little things that make a big difference. Look for dresses with stretch fabric that offer a good balance of structure and give—think ribbed knits for a bit of texture, or smooth jersey for that barely-there feel. Consider the neckline, the sleeve length, and even the hem—these details can take your look from casual to elevated in a snap. If you’re curating a lineup for every occasion, don’t skip the classics: a neutral or jewel-toned maxi stretch dress is endlessly versatile, while a bold print or pop of color adds energy to your winter wardrobe. And if you’re building out your collection, don’t miss our edit of Black Stretchy Dresses—because nothing beats the timeless appeal (and outfit repeat potential) of a little black stretch dress. However you style it, a stretchy maxi dress is more than just a seasonal staple—it’s the foundation for looking and feeling like your best self, no matter what’s on your calendar.

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