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!
Home Cool Weather Dresses
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- Price - High to Low
$48.90
An elegant black off-the-shoulder midi dress with ruched sides and a flattering bodycon fit.
$44.90
A grey ribbed knit midi dress featuring a sweetheart neckline with a twist accent and long sleeves.
$49.90
A pink mesh and knit bodycon midi dress featuring cold-shoulder details, ruching, and padded cups.
$35.90
A chic red-brown bodycon mini dress with a one-shoulder neckline and soft hacci knit fabric.
$19.97 $32.90 39% off
A cozy ivory mini dress with a striped ribbed knit, off-the-shoulder design, and A-line 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: M | Rhinestone
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 | 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 Wine | Size: S | 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: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
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: S | Knit 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 Brown | Size: XS | Knit Fabric/Mesh Fabric
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
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
Cool Weather Dresses
When the temperature drops and the calendar flips to November, your dress rotation deserves a cold-weather upgrade. Cool weather dresses are the ultimate answer to those “I want to be cozy, but I still want to look cute” days. Think plush knits, soft ribbed fabrics, and velvet textures that feel as good as they look—each one designed to keep you warm without sacrificing style. Whether you’re headed to brunch, dashing between classes, or just want to feel put-together for a coffee run, these dresses are your ticket to effortless layering. It’s all about smart details: long sleeves that actually cover your wrists, turtleneck silhouettes that double as built-in scarves, and midi or maxi lengths that play nice with tights or leggings. Even your favorite summer slip dress can get a second life—just add a chunky sweater, a pair of boots, and you’re set for the season. The casual dress windsor vibe is all about versatility: wear it solo with sneakers for a laid-back look, or pile on a tailored coat and statement boots when you need that extra bit of warmth.
Cool weather dresses aren’t just practical—they’re a style statement all on their own. They’re the go-to for anyone who wants to stay warm without layering on bulk, and they make a thoughtful gift for friends who are always cold (we all have that one friend). Picture this: a sweater dress paired with knee-high boots and a wool beret for a stroll through the city, or a velvet midi dress that catches the light at every holiday party. These pieces are made for everything from Friendsgiving dinners to last-minute date nights, and they transition seamlessly from day to night with a quick accessory swap. Corduroy dresses add a vintage touch, while rich jewel tones and textured knits bring a sense of luxury to everyday dressing. If you’re shopping for someone else, these dresses are a safe bet—easy to fit, endlessly wearable, and guaranteed to earn compliments. And if you’re treating yourself (which, let’s be honest, you totally deserve), you’ll love how these styles make getting dressed in the morning feel like less of a chore and more of a celebration.
Styling cool weather dresses is all about the art of layering and mixing textures. Start with a thermal or fitted turtleneck underneath for extra insulation, then add a structured blazer or oversized cardigan for a look that’s equal parts polished and cozy. Tights or leggings are your secret weapon for warmth, and don’t underestimate the power of a great pair of boots—ankle, combat, or knee-high, depending on your mood. Accessories like chunky scarves, slouchy beanies, and leather gloves aren’t just functional, they’re the finishing touches that pull your outfit together. If you’re craving more inspiration or want to explore the full spectrum of seasonal styles, check out our curated selection of Winter Fashion Dresses for even more ways to make your cold-weather wardrobe work overtime. This season, embrace the chill with confidence—because with the right dress, you’re ready for whatever the forecast throws your way.










