Winter Casual Dresses

Winter casual dresses are here to make your cold-weather wardrobe sizzle with style! Whether you're layering up for a cozy coffee date or strutting your stuff at a festive gathering, these dresses are your go-to for effortless chic. Think of them as your fashion-forward BFFs, blending warmth and trendiness like a hot cocoa on a snowy day. With an array of colors, cuts, and textures that scream "you've got this," you'll be turning heads and breaking hearts all season long. So, get ready to slay the winter blues away with these must-have pieces that promise to keep you looking fabulous from brunch to bonfire!

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Windsor Dinner Date Off-The-Shoulder Long Sleeve Midi Dress in Black

$48.90

An elegant black off-the-shoulder midi dress with ruched sides and a flattering bodycon fit.

Windsor Keeping Knit Cute One-Shoulder Long Sleeve Mini Dress in Red Brown

$35.90

A chic red-brown bodycon mini dress with a one-shoulder neckline and soft hacci knit fabric.

The Essential High-Slit Ribbed Knit Midi Dress in Black

$42.90

A black ribbed knit midi dress featuring a turtleneck, long sleeves, and a high side slit.

Windsor Sculpted Chic Ribbed Knit Midi Dress in Grey

$44.90

A grey ribbed knit midi dress featuring a sweetheart neckline with a twist accent and long sleeves.

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Mayra Formal Satin Slit Long Dress in Navy Blue-2

$29.97 $59.90
50% off

(185)

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

Windsor Bethanie Formal Sequin V-Neck Mermaid Dress in Pink-2

$109.90

(94)

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: XXS | Knit Fabric/Mesh Fabric/Mesh Fabric

Shayla Strapless Corset Lace Formal Dress in Red

$159.90

(76)

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

Amirah Formal Glitter Cowl Neck Column Dress in Green

$59.90

(75)

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: M | Knit Fabric

Windsor Jamie Lace-Up Satin Formal Column Dress in Red

$89.90

(73)

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

(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 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

Winter Casual Dresses

When February rolls around and winter is at its peak, the hunt for the perfect casual dress becomes less about braving the cold and more about embracing it—stylishly, of course. This is the season for cozy textures, easy silhouettes, and those little details that make getting dressed feel like a treat, not a chore. Think soft knits that feel like a hug, sweater dresses with just enough structure to flatter, and long sleeves that don’t sacrifice style for warmth. Windsor casual dresses are designed for this exact moment: the in-between of hibernation and social butterfly, where you want to look put together but still be comfortable enough to binge your favorite show, run errands, or spontaneously say yes to a coffee date. Layering is your best friend—throw on a chunky cardigan, slip into tights, or add boots to instantly winterize your look. Whether you’re heading to class, catching up with friends, or just need an outfit that works from brunch to grocery runs, winter dresses casual enough for every plan (or lack thereof) make life infinitely easier. It’s about curating a closet that works as hard as you do, with pieces that transition effortlessly from one vibe to the next.

Gifting a winter dress is basically wrapping up a season’s worth of comfort and confidence. Picture this: your best friend’s birthday falls right in the middle of a cold snap, and you want to give her something that feels both thoughtful and genuinely useful. A versatile winter dress checks every box—practical, stylish, and something she’ll actually wear on repeat. These dresses also make great surprises for sisters who are always “borrowing” your clothes, or as a little self-gift when you need a pick-me-up (because yes, retail therapy is real and sometimes necessary). The appeal of windsor winter dresses lies in their ability to suit every personality and occasion. Some days call for a relaxed, oversized fit that pairs perfectly with a messy bun and sneakers; others, for a more tailored shape that looks right at home under a statement coat. The best part? These aren’t one-and-done pieces. With the right accessories, a winter dress can go from a casual daytime staple to a dinner-ready ensemble—just swap your boots for heels, add a bold lip, and you’re set. If you’re feeling the urge to dial up the romance or need something a little extra for a special night out, you can always explore the edit of Winter Date Dresses for inspiration that’s just as seasonally on point.

No matter how you wear them, winter dresses casual enough for daily life are the unsung heroes of the colder months. They solve the “I have nothing to wear” spiral with ease, offering up endless outfit combinations that don’t require a style degree to pull off. The beauty is in the details: ribbed cuffs that keep out the chill, midi lengths that feel modern and practical, and colors that range from classic neutrals to bold, mood-boosting shades. Windsor casual dresses are built for real life—think spontaneous coffee runs, impromptu road trips, or just the everyday hustle. They’re the pieces you reach for when you want to look good without overthinking it, when you need to feel cozy but still want to turn heads. Whether you’re shopping for yourself or searching for a gift that’s guaranteed to get worn (and complimented), winter dresses are a wardrobe investment that pays off every time you slip one on.

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Winter Casual Dresses

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