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!
$39.90
A brown knit midi dress with long sleeves, off-the-shoulder neckline, and ruched bodycon fit.
$9.97 $38.90 74% off
A brown knit bodycon midi dress with flare cuff sleeves and a stylish V-neckline.
$29.90
A trendy brown striped knit mini dress with a mock neckline and long fitted sleeves.
$36.90
A natural rib knit mini dress with a folded off-the-shoulder neckline and flattering skater silhouette.
$48.90
An elegant black off-the-shoulder midi dress with ruched sides and a flattering bodycon fit.
$35.90
A chic red-brown bodycon mini dress with a one-shoulder neckline and soft hacci knit fabric.
$54.90
A black ribbed knit midi dress with a tie-dye pattern, scoop neckline, and back slit.
$44.90
A grey ribbed knit midi dress with a sweetheart neckline and twist accent, perfect for casual outings.
$9.97 $44.90 78% off
A black velvet floral mini dress with sheer sleeves and a sweetheart neckline for holiday events.
$21.97 $42.90 49% off
A brown ribbed knit mini dress with a scoop neckline and faux topper long 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.
$9.97 $49.90 80% off
A chic navy blue mini dress with velvet fabric, cowl neckline, and ruched bodycon silhouette.
$38.90
A burgundy knit skater dress featuring a cold-shoulder design and corset-style seams for stylish flair.
$28.90
A black gauze midi dress featuring a flowy silhouette, V-neckline, adjustable straps, and hidden side pockets.
$9.97 $38.90 74% off
A wine-colored velvet mini dress with a sweetheart neckline, flare sleeves, and bodycon silhouette.
$32.90
A cozy ivory mini dress with a striped ribbed knit, off-the-shoulder design, and A-line silhouette.
$49.90
A strapless black woven midi dress featuring a color block bodice, flowy hem, and hidden side pockets.
Now Trending
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
Shine bright and sparkle up the night in the gorgeous Leila mini dress. The dress boasts an alluring open back with a lace-up strappy design for a customized fit, and a short, curve-hugging silhouette. Shop Long Version: Kailani Formal Sequin Slit Mermaid DressFit & FeaturesSheer mesh fabric, full knit lining, moderate stretch, Sequin embroidery, scroll pattern, Sleeveless square neckline, adjustable spaghetti straps, Open back, lace-up strappy design, tie closure, High waist seam, lower back zipper, hook and eye closure, Mini-length hem, fitted bodycon silhouette, Runs true to size, Where to Wear:Prom, bachelorettes, birthdays, Vegas weekends, date nights Free Shipping on All Orders Over $75. | Windsor Leila Sequin Bodycon Mini Dress in Royal Blue | Size: XL | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
Look and feel like a sultry senorita in this mesh mini dress perfect for an chic night on the town! It features a sleeveless cowl neckline, dual adjustable spaghetti straps with a tie-neck closure, and side and back ruched seams designed to flaunt your curves along the bodycon silhouette. Complete the look with hoop earrings. Fit & FeaturesSleeveless cowl neckline, Dual adjustable spaghetti straps, tie-neck closure, Side and back ruched seams, Back zipper and hook-eye closure, Bodycon silhouette, mini-length hem, Mesh fabric, brushed soft knit stretchy lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Senorita Mesh Strappy Mini Dress in Red | Size: M | Knit Fabric/Mesh Fabric/Mesh Fabric
Every occasion is worth celebrating in this off-the-shoulder midi dress! The smooth and stretchy knit fabric includes a full-length knit lining for additional coverage. The off-the-shoulder neckline and short-sleeve cuffs add a touch of elegance, while the bodycon silhouette and flared midi-length hem accentuate your curves in all the right places. Complete the look with teardrop earrings and heels. Fit & FeaturesSmooth stretchy knit fabric with knit lining, Off-the-shoulder neckline, Short-sleeve cuffs, Bodycon fit, Flare hem, Style runs small, Free Shipping on All Orders Over $75. | Windsor Exceptional Off-The-Shoulder Flared Midi Dress in Natural | Size: XS | Knit Fabric
Bring on the cute attitude in this ponte mini skort brings featuring a flattering high-rise waist, and a skirt overlay designed with dual front slits along the form-hugging fit. Fit & FeaturesSmooth ponte knit fabric, minimal stretch, High-rise waist, Skirt overlay, dual front slits, Form-hugging silhouette, Mini-length hem, Shorts lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cute Attitude Ponte Slit Mini Skort in Black | Size: XL | Knit Fabric
Show up and stun this formal season in the gorgeous Brynlee bodycon mini dress! She features a sleeveless square neckline, a built-in padded bust, halter spaghetti straps, an open back with a lace-up design for a customized fit, and a short, curve-hugging silhouette. The lined mesh fabric features all-over sequin embroidery in an intricate scroll pattern. Style the formal mini dress with clear heels for a night to remember. Fit & FeaturesSleeveless, square neckline, Built-in padded bust, no bra required, Halter spaghetti straps, back button closure, Open back, lace-up design, zipper closure, Bodycon silhouette, mini-length hem, Sequin scroll embroidery, mesh fabric, knit lining, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Brynlee Sequin Embroidered Bodycon Dress in Sage | Size: S | Knit Fabric/Mesh Fabric/Mesh Fabric
A mini dress that brings the luxe sensation! The Keira faux pearl short dress is a stunning style with a strappy tie-back design and a bodycon silhouette that highlights your figure. Fit & FeaturesLightweight mesh fabric, stretchy knit lining, Faux pearl and bead embellishments, Sleeveless cowl neckline, Spaghetti straps, strappy tie-back design, open-back, Bodycon silhouette, mini-length hem, Runs true to size, Where to Wear:Prom, birthday parties, bachelorettes, Vegas weekends, rooftop cocktails Free Shipping on All Orders Over $75. | Windsor Keira Faux Pearl Strappy Open-Back Mini Dress in Light Blue-2 | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
A fashionista like you will adore this basic mini skirt for creating your day and night looks! Featuring an elasticized high-rise waistband, bodycon silhouette, and a flirty front hem slit on stretchy and smooth knit fabric. Style with a corset top and heels. Fit & FeaturesHigh-rise elasticized waistband, Bodycon silhouette, Front hem slit, Mini-length hem, Stretchy and smooth knit fabric, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Get Down With Basic Slit Mini Skirt in Black | Size: XL | Knit Fabric
Everyone will see you shining at the club in this glitter mini dress! It features an off-the-shoulder sweetheart neckline, sheer fitted ruched long sleeves, adjustable spaghetti straps, a ruched seam along the padded bust, a sheer bodice with trim, and side ruched seams that hug your curves on the bodycon silhouette. Complete the look with a clutch and heels. Fit & FeaturesOff-the-shoulder sweetheart neckline, Adjustable spaghetti straps, Sheer fitted ruched long sleeves, Ruched and padded bust, sheer bodice, trim, Side ruched seams, bodycon silhouette, mini-length hem, Glitter mesh fabric, sewn-in knit lining, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor See Me Shining Glitter Off-The-Shoulder Mini Dress in Wine | Size: M | Knit Fabric/Mesh Fabric/Mesh Fabric
Both sexy and demure, the Kristen party dress wows from every angle! Perfect for bachelorette weekends, themed soirees, and formal birthdays! She features a sleeveless sweetheart neckline with a padded bust, cowl draping, adjustable spaghetti straps, and side ruched seams that hug your curves along her short bodycon silhouette. The formal party dress is composed of a faux pearl embellished mesh fabric with a stretchy knit lining. Complete the look in statement block heels. Fit & FeaturesSleeveless sweetheart neckline, Padded bust, cowl draping, Adjustable spaghetti straps, Side ruched seams, bodycon silhouette, Mini-length hem, Faux pearl embellishments, mesh fabric, stretch knit lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Kristen Faux Pearl Mini Party Dress in White | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
Winter Casual Dresses
When it comes to effortless style, casual winter dresses are basically your wardrobe’s secret weapon. These laid-back looks are perfect for those days when you want to look put together without trying too hard—think running out for coffee, impromptu brunch plans, or even just hanging out with your girls, swapping stories that get louder with every refill. Windsor casual dresses are made for the moments you want to feel cozy but still show off your personal style, whether you’re layering up for a chilly day out or just want something cute and comfy to lounge in. The beauty of a windsor casual dress lies in its versatility: toss it on with chunky boots and a denim jacket for that “off-duty model” vibe, or layer it over tights and under a long cardigan when you’re feeling extra snuggly. And if you’re the queen of accessorizing, these dresses are your blank canvas—add a beanie, a killer belt, or your favorite statement earrings and you’re ready to turn the sidewalk into your runway.
Gift shopping? Windsor dresses casual styles are a total win for birthdays, bestie surprises, or just because you want to make someone’s day. There’s something about slipping into a casual dress that feels like a little act of self-care—like you’re treating yourself to comfort and confidence all at once. These dresses are the kind of thing your BFF will thank you for when she’s racing from class to coffee dates, or your sister will reach for on those “I have nothing to wear” mornings. And let’s be real, gifting one of these dresses is basically giving the gift of good vibes and main character energy. When you’re picking out your perfect fit, think about what makes you feel unstoppable: a swingy silhouette for maximum twirl potential, a ribbed knit for that hugs-you-in-all-the-right-places feel, or maybe a shirt dress you can cinch at the waist for instant polish. Fit and fabric matter—look for soft, stretchy knits that move with you, or cozy sweater dresses that keep you warm without the bulk. It’s all about finding that sweet spot between style and comfort, so you can slay from sunrise to last call.
The best part about windsor casual dresses is how they’re made for real life—messy hair, spontaneous plans, and all. You can dress them down for a lazy day in, or style them up for dinner with your crush (pro tip: if you’re looking to turn up the romance, check out our Winter Date Dresses for even more inspo). No matter how you wear them, these dresses are your ride-or-die for keeping things cute and cozy. Whether you’re shopping for yourself or picking out the perfect gift for someone who deserves a little extra love, you can’t go wrong with a casual winter dress that’s as fearless and fun as you are.