Cool Weather Dresses
Cool weather dresses are your secret weapon for slaying those chilly days with style and sass. When the temperature drops, it's time to layer up without sacrificing an ounce of fabulousness. Picture yourself wrapped in cozy chicness, whether you're strutting down city streets or sipping cocoa by the fire. These dresses are here to keep you warm and on-trend, offering versatility that pairs perfectly with your favorite boots and jackets. So, grab your pumpkin spice latte and let's make some unforgettable cool weather memories!
$36.90
A natural rib knit mini dress with a folded off-the-shoulder neckline and flattering skater silhouette.
$36.90
An elegant sage off-the-shoulder midi dress with a bodycon fit and flared hem.
$44.90
A sophisticated white midi dress with chiffon sleeves, a square neckline, and a ruched bodycon silhouette.
$46.90
A brown woven midi dress with a ditsy floral print, corset bodice, and high front slit.
$20.97 $46.90 55% off
A black floral midi dress with a corset bodice, sweetheart neckline, and flirty front slit.
$48.90
An elegant black off-the-shoulder midi dress with ruched sides and a flattering bodycon fit.
$49.90
A pink mesh and knit bodycon midi dress featuring cold-shoulder details, ruching, and padded cups.
$42.90
A black ponte mini dress with sheer chiffon sleeves and a playful square neckline.
$9.97 $39.90 75% off
A black mini dress with a cutout bust, ruched wrap design, and sheer mesh long sleeves.
$49.90
A white cold shoulder midi dress featuring a bodycon silhouette with ruched seams and padded cups.
$21.97 $42.90 49% off
A brown ribbed knit mini dress with a scoop neckline and faux topper long sleeves.
$42.90
An abstract print maxi dress with a ruched bodycon silhouette and sheer off-the-shoulder sleeves.
$42.90
A black ribbed knit bodycon mini dress with trendy cutouts and lattice accents for a chic look.
$36.90
A cozy heather grey ribbed knit mini dress with an off-the-shoulder neckline and A-line silhouette.
$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.
$59.90
A green velvet mermaid dress with ruching, adjustable straps, and a high front slit.
$32.90
A cozy ivory mini dress with a striped ribbed knit, off-the-shoulder design, and A-line silhouette.
$9.97 $38.90 74% off
A wine velvet mini dress with a sweetheart neckline, flare sleeves, and a bodycon silhouette.
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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
Cool Weather Dresses
When it comes to dressing for cool weather, it’s all about keeping things cozy without sacrificing your signature style. Think of cool weather dresses as your wardrobe’s secret weapon—the piece that lets you flirt with the chill while still looking like you own every room you walk into. From coffee runs to late-night adventures, these dresses are made for the girl who’s always on the move but never misses a chance to make a statement. Imagine slipping into a soft knit dress that hugs you just right, or rocking a midi with boots that were made for strutting. The best cool weather dresses are crafted from warm, touchable fabrics like chunky knits, plush fleece, and even luxe velvet, each one ready to be layered up or down depending on your vibe (and the forecast). Whether you’re layering a fitted turtleneck underneath or throwing on a slouchy cardigan, you’re in control—mixing textures, playing with lengths, and adding your favorite accessories to create a look that’s as unique as you are. And let’s be real: there’s nothing like the confidence boost that comes from knowing you look fire *and* feel comfortable, even when the temperature drops.
Cool weather dresses make the ultimate gift for your ride-or-die bestie, your sister, or even yourself—because self-love is always in season. They’re the kind of pieces that transition seamlessly from day to night, from brunch dates to bonfire hangs, giving you endless ways to express your style. Picture yourself wrapped up in a ribbed sweater dress, belted at the waist for that hourglass moment, or twirling in a flared knit skirt that brings a little extra drama to every step. These dresses aren’t just about staying warm; they’re about making memories—like spontaneous road trips, rooftop parties with the squad, or those cozy nights in that turn into heart-to-hearts. Don’t forget to play with layers: toss on a denim jacket, slip into some tall boots, or add a pop of color with a chunky scarf. The right dress for cool weather works overtime, letting you dress for whatever the day (or night) throws at you, all while keeping your look fresh and your confidence sky-high.
For anyone building a wardrobe that can handle whatever comes next—chilly mornings, surprise plans, or just those days when you want to look put-together without overthinking it—cool weather dresses are the MVP. They’re perfect for gifting, easy to style, and always ready to help you serve main character energy. If you’re loving the vibe and want even more inspo for how to stay cute when the temps dip, check out our Winter Casual Dresses for a curated selection that’ll keep your closet (and your mood) on point all season long.