Holiday Casual Dresses
Get ready to sleigh this festive season with our fabulous collection of holiday casual dresses! Whether you're sipping cocoa by the fire or dancing under twinkling lights, these dresses are your ultimate go-to for every merry occasion. From chic and cozy to effortlessly elegant, we've got the perfect looks to keep you shining bright all season long. So, slip into something stunning and let the festivities begin—because, girl, you're about to be the star on top of the holiday style tree!
$36.90
An elegant sage off-the-shoulder midi dress with a bodycon fit and flared hem.
$32.90
A sage satin off-the-shoulder mini dress with a flattering A-line silhouette for special occasions.
$46.90
A black glitter crepe knit mini dress with sheer bell sleeves and a bodycon silhouette.
$39.90
A brown knit midi dress with long sleeves, off-the-shoulder neckline, and ruched bodycon fit.
$9.97 $42.90 77% off
A grey glitter knit mini dress with a one-shoulder design and ruched side seams.
$32.90
A chic red sleeveless midi dress with ruched seams and a curve-hugging bodycon silhouette.
$49.90
A lavender glitter skater dress with sheer peasant sleeves and a fit and flare silhouette.
$29.90
A strapless brown lace mini dress with a flared hanky hem for standout occasions.
$9.97 $42.90 77% off
A slate A-line mini dress with a V-neckline and ruffled hem in soft knit fabric.
$9.97 $44.90 78% off
A black velvet floral mini dress with sheer sleeves and a sweetheart neckline for holiday events.
$46.90
An olive green gauze skater dress featuring V-neck cutouts, flowy sleeves, and a breezy silhouette.
$42.90
A blue paisley halter skater dress featuring a smocked bust, ruffled hem, and flowy woven fabric.
$22.97 $49.90 54% off
A black woven mini dress with pleated A-line silhouette and spaghetti strap ties for casual outings.
$29.90
A trendy brown striped knit mini dress with a mock neckline and long fitted sleeves.
$49.90
A strapless black woven midi dress featuring a color block bodice, flowy hem, and hidden pockets.
$28.90
A black gauze midi dress featuring a flowy silhouette, V-neckline, adjustable straps, and hidden side pockets.
$9.97 $36.90 73% off
A green velvet mini dress with a pleated bust, spaghetti straps, and glitter accents.
$36.90
A denim satin mini dress with a ruched wrap silhouette and spaghetti straps for a chic look.
$59.90
A white mini dress with iridescent sequins, sheer velvet fabric, and adjustable spaghetti straps.
$79.90
A sage mini dress with faux pearl embellishments, strappy open back, and bodycon silhouette.
$52.90
A white mini bodycon dress with faux pearl embellishments and adjustable spaghetti straps.
$39.90
A chic white glitter lace dress with a bodycon fit, perfect for weddings or special occasions.
$35.90
A sage bodycon mini dress with a pleated cowl neckline and stretchy knit fabric.
$38.90
A charming white A-line dress with a sweetheart neckline and adjustable spaghetti straps.
$40.90
A royal blue glitter mesh mini dress featuring a halter cowl neckline, ruched sides, and bodycon fit.
$37.90
A denim satin strapless mini dress with a pleated bust and flattering bodycon silhouette.
$9.97 $59.90 83% off
A shimmery black sequin party dress featuring a one-shoulder design and bodycon wrap silhouette.
$49.90
A pink sequin mini dress with a lace-up back and iridescent scroll pattern embroidery.
$59.90
A glamorous black bodycon dress with glitter knit fabric, off-the-shoulder neckline, and high slit.
$64.90
A black bodycon mini dress with sheer sleeves and sparkling rhinestones for a glamorous look.
$64.90
A sage skater dress with a lace-trimmed sweetheart neckline and adjustable lace-up back.
$44.90
A blue glitter knit mini dress featuring a pleated cowl neckline, spaghetti straps, and asymmetric wrap hem.
$46 $64.90 29% off
A dazzling white sequin party dress with a sweetheart neckline and adjustable spaghetti straps.
$32.90
A strapless yellow mini dress with ruched sides and a playful ruffled hem in knit fabric.
$46.90
A lime yellow strapless mini dress featuring all-over sequins, sheer mesh fabric, and a bodycon silhouette.
$42.90
A sultry pink strapless mesh mini dress with ruffle trim and bodycon silhouette for standout style.
$48.90
An elegant black off-the-shoulder midi dress with ruched sides and a flattering bodycon fit.
$36.90
A green mini-length bodycon dress featuring a pleated sweetheart bust and open back with criss-cross straps.
$22.97 $49.90 54% off
A shimmering pink sequin mini dress with a plunge halter V-neckline and flattering A-line silhouette.
$99.90
A sophisticated black velvet high-low dress with a one-shoulder neckline and ruffle trim.
$42.90
A strapless ivory lace skater dress with ruffled hem, perfect for prom nights.
$59.90
A light blue strapless glitter party dress with a V-neckline, padded cups, and hidden pockets.
$36.90
A sage halter skater mini dress crafted from stretchy rib knit fabric for a fabulous look.
$35.90
A chic red-brown bodycon mini dress with a one-shoulder neckline and soft hacci knit fabric.
$46.90
A navy blue strapless mini skater dress in stretchy poplin with a ruched bodice and pleated hem.
$49.90
A natural floral skater dress featuring a corset-inspired bodice, pleated trim, and cotton woven fabric.
$46.90
An ivory striped midi dress with cutouts, adjustable straps, and dual side slits for casual elegance.
$9.97 $42.90 77% off
A green glitter knit mini dress with an off-the-shoulder neckline and fitted long sleeves.
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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: S | 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
Holiday Casual Dresses
There’s something about holiday casual dresses that just gets the party started before you even walk in the door. Maybe it’s the way a soft, flowy skirt sways as you breeze past the dessert table, or how a perfectly draped dress in a rich wine hue makes you feel like the main character in your own festive rom-com. Holiday get-togethers call for that sweet spot between laid-back and luxe—think easy-breezy silhouettes, playful details, and fabrics that let you move with confidence, whether you’re hosting a gift swap with your ride-or-die crew or catching up with family over cocoa and charcuterie. Windsor casual dresses are made for those moments when you want to look put-together without trying too hard, blending comfort with a dash of sparkle. Picture this: you’re slipping into a soft knit dress that hugs in all the right places, or maybe a shirt dress with just enough shine to catch the twinkle lights. Effortless, right? That’s the magic of holiday casual—dresses you can dress up with bold hoops and heels or keep chill with sneakers and a denim jacket, depending on your vibe.
Holiday casual dresses are the secret weapon for anyone with a packed social calendar and a closet that needs to keep up. They’re the go-to for brunches that turn into shopping sprees, Friendsgiving feasts, and those “just because” nights out when you want to feel cute without going full glam. And let’s be real—these dresses are also the ultimate gift for your bestie who’s always RSVP-ing yes, your sister who loves a good wardrobe refresh, or even your mom who’s ready to trade in her classic cardigans for something a little more playful. With so many styles to choose from—think wine colored dresses casual enough for daytime hangs but still elevated for evening plans—there’s a look for every personality and every plan. The best part? These dresses are designed to last beyond the holiday snaps, seamlessly taking you from festive gatherings to everyday adventures. Whether you’re all about those flirty ruffles, sleek bodycon fits, or easy wrap styles, there’s a Windsor holiday dress that feels like it was made just for you. And if your calendar suddenly calls for something with a bit more drama (hello, candlelit dinners and VIP invites), you can always level up your look by checking out our Holiday Formal Dresses for that extra wow factor.
When you’re shopping for the perfect holiday casual dresses, it’s all about finding pieces that make you feel unstoppable—like you could take on any celebration, planned or spontaneous. Look for dresses that mix festive touches with everyday comfort: soft ribbed knits, playful puff sleeves, or a pop of shimmer that catches the light just right. Don’t sleep on those versatile styles you can throw on and go, but still look like you spent hours getting ready (even if you hit snooze one too many times). Windsor casual dresses are made for mixing, matching, and making memories. Layer them up with cozy cardigans or faux leather jackets, swap out your shoes to go from day to night, and don’t forget those little accessories that make every outfit feel like a celebration. Whether you’re gifting a dress to your favorite trendsetter or treating yourself to a look that’ll turn heads at every gathering, holiday casual dresses are your ticket to showing up, showing out, and making every moment a little more magical.