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!

Show Filters

Sort: Recommended

Size

Color

Price

All Filters

27 results

Sort

Windsor Lucy Taffeta Bow Mini Party Dress in White

$79.90

A white taffeta mini dress featuring a detachable bow with a dramatic train for stunning entrances.

Windsor Keira Faux Pearl Strappy Open-Back Mini Dress in Pink

$79.90

A pink mini dress with faux pearl embellishments, cowl neckline, and strappy open-back design.

Windsor Always Effortless Halter Bodycon Mini Dress in Yellow

$42.90

A vibrant yellow halter bodycon mini dress in stretchy knit fabric, perfect for any occasion.

Windsor Giada Glitter Knit Off-the-Shoulder Column Dress in Black

$59.90

A glamorous black bodycon dress featuring glitter knit fabric, off-the-shoulder neckline, and high slit.

Windsor Yesenia Formal Rhinestone Mini Dress in Black

$64.90

A black bodycon mini dress with sheer sleeves and sparkling rhinestone embellishments for formal occasions.

Pretty Vibes Eyelet Knit Layered Skater Dress in White-2

$32.90

A breezy white eyelet knit skater dress featuring a square neckline and double-layered flared skirt.

Windsor Flirt Mode On Lace Tiered Halter Mini Dress in Black

$46.90

A black knit halter mini dress featuring lace trim, ruffle tiers, and a strappy open back.

Now Trending

Windsor Classics Lover Off-The-Shoulder Satin A-Line Mini Dress in Yellow

$34.90

(98)

This satin mini dress will be your favorite for celebrations, events, and date nights! Sleek and smooth satin shapes this off-the-shoulder dress, which features a flattering A-line silhouette perfect for styling with heels. Fit & FeaturesSmooth and sleek satin fabric, stretchy knit lining, Off-the-shoulder neckline, Short sleeve cuffs, A-line silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Classics Lover Off-The-Shoulder Satin A-Line Mini Dress in Yellow | Size: XS | Knit Fabric/Satin Fabric

Sale

Windsor Senorita Mesh Strappy Mini Dress in Light Blue

$23 $32.90
30% off

(94)

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 Light Blue | Size: L | Knit Fabric/Mesh Fabric/Mesh Fabric

Windsor Lucy Taffeta Bow Mini Party Dress in White

$79.90

(73)

The Lucy mini party dress is sleek and simple from the front and stunning from the back. Turn heads as you stun from the back with a flirty big bow tie with a dramatic train that glides against the floor! Fit & FeaturesTaffeta structured woven-lined fabric, slight stretch, Strapless, square neckline, non-slip grip, Hidden side zipper, hook and eye closure, Front and back pleating and ruching, Form-hugging, mini-length hem, Detachable back bow with train, Runs true to size, Where to Wear:Prom, weddings, brides, bachelorettes, big birthday events, fancy date nights, gorgeous dinner parties, cocktail soirees, rehearsal dinners, engagement photoshoots and parties Free Shipping on All Orders Over $75. | Windsor Lucy Taffeta Bow Mini Party Dress in White | Size: XS

Windsor Cute Attitude Ponte Slit Mini Skort in Black

$27.90

(69)

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: L | Knit Fabric

Lena Strapless Bodycon Beaded Mesh Mini Dress in White

$84.90

(64)

Express your devotion to romance in the Lena mesh mini dress perfect for modern brides, birthday girls, or graduates! The strapless cowl neckline adds a touch of elegance, while the bodycon fit accentuates your figure. Fit & FeaturesBeaded mesh fabric, stretchy knit lining, Strapless cowl neckline, Back zipper and hook-eye closure, Bodycon fit, mini-length hem, Runs true to size, Where to Wear:Prom, date nights, bachelorettes, girl's night out, birthdays Free Shipping on All Orders Over $75. | Windsor Lena Strapless Bodycon Beaded Mesh Mini Dress in White | Size: XL | Knit Fabric/Mesh Fabric/Mesh Fabric

Get Down With Basic Slit Mini Skirt in Black

$16.90

(57)

Minimal, but never boring. This sleek mini skirt brings the heat with a flirty slit and body-hugging fit made for going out or dressing up your everyday looks. Fit & FeaturesStretchy and smooth knit fabric, High-rise elasticized waistband, Mini-length hem, short front slit, Bodycon silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Get Down With Basic Slit Mini Skirt in Black | Size: M | Knit Fabric

Windsor Flawless Allure Cowl Neck Bodycon Mini Dress in Black

$35.90

(49)

Show off a flawless allure in this figure-flaunting mini dress! Designed with a sleek knit fabric with a fab sheen, this mini-length dress offers plenty of stretch so you can dance all night. The sleeveless bodice is shaped with a pleated cowl neckline for a chic draped effect and spaghetti straps. The pleating across the bodycon silhouette will accentuate your stunning curves. Style with metallic heels for a club night out.Fit & FeaturesStretchy sleek knit fabric, Sleeveless pleated cowl neckline, Spaghetti straps, Pleating, Bodycon fit, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flawless Allure Cowl Neck Bodycon Mini Dress in Black | Size: M | Knit Fabric

Catalina Rhinestone And Pearl Formal Mini Dress in Yellow

$69.90

(44)

Bling on the sultry glamour with the sparkling details of the stunning Catalina formal mini dress with a bodycon silhouette that will flaunt your gorgeous figure! Fit & FeaturesSheer mesh fabric, full-length knit lining, plenty of stretch, Mini iridescent rhinestones, faux pearl embellishments, Sleeveless cowl neckline, Adjustable spaghetti straps, Mini-length hem, bodycon silhouette, Runs true to size, Where to Wear:Prom, bachelorettes, birthdays, girl's night out, date nights Free Shipping on All Orders Over $75. | Windsor Catalina Rhinestone And Pearl Formal Mini Dress in Yellow | Size: M | Knit Fabric/Rhinestone/Mesh Fabric

Perfect Glow Strapless Pleat A-Line Satin Mini Dress in Gold

$39.90

(33)

You'll have that perfect glow in this satin mini dress at the party! This stunning mini-length dress features a strapless neckline for a classic style, and a side pleated seam adds a touch of sophistication and creates a flattering A-line silhouette. Complete the look with stiletto heels. Fit & FeaturesSatin fabric lined with stretchy knit, Strapless neckline, Side pleated seam, A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Perfect Glow Strapless Pleat A-Line Satin Mini Dress in Gold | Size: L | Satin Fabric

Windsor Paige Rhinestone Formal Bodycon Mini Dress in Red

$59.90

(26)

Capture all the attention with your sultry allure in the Paige rhinestone formal bodycon mini dress! She features a sleeveless cowl neckline, adjustable spaghetti straps for a customized fit, all-over rhinestone embellishments for that total glam girl vibe, a mini-length hem, and a bodycon silhouette to hug your gorgeous curves. The slinky knit fabric offers plenty of stretch. Style this mini dress with metallic heels for your next dressy night out! Fit & FeaturesSleeveless cowl neckline, Adjustable spaghetti straps, All-over rhinestone embellishments, Mini-length hem, bodycon silhouette, Slinky knit fabric, full-length knit lining, plenty of stretch, Runs true to size, Where to Wear:School dances, date nights, bachelorettes, birthdays, cocktail parties, rooftop hotel bars, GNO, parties Free Shipping on All Orders Over $75. | Windsor Paige Rhinestone Formal Bodycon Mini Dress in Red | Size: S | Knit Fabric/Rhinestone

Holiday Casual Dresses

When your calendar is dotted with low-key celebrations, last-minute get-togethers, or that annual family brunch that always ends with group selfies, the right holiday casual dress is the ultimate wardrobe MVP. February brings its own kind of magic—think cozy dinners, Galentine’s plans, and the kind of indoor-outdoor hangs where you want to look festive but still feel like yourself. That’s where these looks come in. Holiday casual dresses are all about striking the balance between comfort and style, letting you move from a laid-back evening with friends to a spontaneous dinner date without missing a beat. Picture soft knits that feel like your favorite sweater but look like you actually tried, or flowy silhouettes that let you indulge in dessert without a second thought. It’s about easy layering, playful textures, and details that pop just enough to make you feel special—think subtle shimmer, velvet touches, or a statement sleeve that says, “Yes, I do have plans tonight.” Whether you’re shopping for yourself or hunting down a gift for someone whose style is as unpredictable as the winter weather, these dresses tick all the boxes: versatile, photo-ready, and priced so you can grab more than one without side-eyeing your bank account.

The beauty of Windsor holiday dresses is their ability to flex with your plans—and your mood. Maybe you’re the friend who always hosts, so you need something that looks cute with slippers when you’re lighting candles but still holds up for a quick grocery run. Or maybe you’re gifting one to your sister who’s notoriously hard to shop for, but you know she’ll appreciate something that’s as easy to throw on as it is to dress up. These are the dresses you’ll reach for when you want to look put-together with zero effort, the ones that make you feel ready for anything, even if “anything” is just a cozy night in with your favorite people. And if you’re the type who likes to stretch your wardrobe, the right holiday casual dress can absolutely pull double-duty—layer it with a denim jacket for errands, swap sneakers for boots, or add a bold lip for a dinner out. With holiday dresses Windsor makes it easy to stay on trend without feeling overdone, you’ll find yourself building outfits around them long after the last heart-shaped chocolate is gone. And if your plans are headed somewhere sunnier, or you’re already dreaming of spring escapes, don’t sleep on our Casual Vacation Dresses for even more effortless, packable style.

Choosing a holiday casual dress is really about embracing your own version of festive—whatever that looks like this season. Maybe you gravitate toward classic wrap dresses that flatter every curve, or you’re all about playful prints that make a statement without trying too hard. The best part? These dresses are designed to work for every vibe and every body, with thoughtful details that make getting dressed feel less like a chore and more like a celebration. It’s about finding those pieces that make you want to RSVP “yes” just so you have an excuse to wear them. From brunch to book club, movie nights to family dinners, Windsor holiday dresses are the pieces you’ll keep in rotation, ready for every spontaneous invite and every “just because” moment. Because style should always feel this easy—and this much fun.

Reset Your Password

Email Sent

Order Status

Holiday Casual Dresses

Home Holiday Casual Dresses

Now Trending

Holiday Casual Dresses

Related Collections