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!

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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 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.

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Windsor Leila Sequin Bodycon Mini Dress in Royal Blue

$59.90

(147)

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: L | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric

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

$79.90

(66)

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 Pink | Size: M | Knit Fabric/Mesh Fabric/Mesh Fabric

Windsor Toni Glitter Open Back Bow Mini Dress in Red

$59.90

(16)

The Toni glitter mini dress turns every step into a statement. Crafted from a glittering knit, this bodycon mini dress stuns with a clean square neckline, open back, and a cascading bow that brings full drama from behind. Fit & FeaturesGlitter knit stretchy fabric, knit lining, Square neckline, Spaghetti straps, Open back, Back bow with floor-length drape, Bodycon silhouette, mini-length hem, Runs true to size, Where to Wear:Weddings, rehearsal dinners, engagement parties, bridal showers, wedding showers, birthdays, anniversaries, red carpet events, industry parties, photoshoots, date night Free Shipping on All Orders Over $75. | Windsor Toni Glitter Open Back Bow Mini Dress in Red | Size: M | Knit Fabric/Stretchy Fabric

Chic Cutie Ribbed Knit Halter Midi Dress in Olive

$39.90

(14)

Show up to happy hour looking like a chic cutie in this halter midi dress designed with hacci ribbed knit fabric for plenty of stretch. The tie-back halter straps lead to an alluring open back, while the curve-hugging fit flaunts your gorgeous figure. Fit & FeaturesHacci ribbed knit fabric, high stretch, sewn-in knit lining, Sleeveless V-neckline, Tie-back halter straps, Open back, lower ruched seam, Midi-length form-hugging silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Cutie Ribbed Knit Halter Midi Dress in Olive | Size: S | Knit Fabric

Windsor Flirty Details Lace Halter Mini Dress in Ivory

$36.90

(11)

You'll adore the flirty details of this little lace halter dress. It features a cowl neckline, V-shaped drop waist seam, and a mini-length asymmetric hem with a flowy A-line silhouette. Fit & FeaturesSheer lace fabric with knit lining, high stretch, Sleeveless cowl neckline, Halter strap, partially open back, V-shaped drop waist seam, Mini-length asymmetric hem, A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flirty Details Lace Halter Mini Dress in Ivory | Size: M | Lace Fabric/Knit Fabric/Sheer Lace Fabric

Glitz Happens Glitter Halter Mini Dress in Pink

$39.90

(10)

Giving disco diva with a dash of sultry! This glitter mini dress brings the heat with a draped cowl neckline and curve-hugging ruching—aka, the dress that does all the flirting for you. Fit & FeaturesGlitter fabric, sewn-in knit lining, moderate stretch, Halter cowl neckline, Open back with spaghetti strap tie, Ruched bodycon silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Glitz Happens Glitter Halter Mini Dress in Pink | Size: L | Knit Fabric

Guest List Glam Abstract Halter Maxi Dress in Ivory

$42.90

(9)

All eyes on you (as it should be). With a dreamy slit and waist cutouts, this maxi dress is made for RSVPs, rooftop clinks, and compliments you’ll pretend to be shy about. Fit & FeaturesAbstract print, mesh-lined fabric, moderate stretch, Halter cowl neckline, hoop inserts, spaghetti strap tie, Open back, High front ruffled trim slit, Bodice cutout with hoop insert, Curve-hugging, maxi-length silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Guest List Glam Abstract Halter Maxi Dress in Ivory | Size: L

Windsor No Apologies Open Back Halter Dress in Black

$42.90

(7)

This halter mini dress is doing everything — plunging neckline, open back drama, and a front sash detail that hits just right. The sleek, body-hugging fit creates a sculpted silhouette while the soft stretch fabric keeps it comfortable for dinner and dancing. Fit & FeaturesSmooth stretch fabric, Halter neckline with plunging V front, Open back silhouette, Gold-tone hardware detail at bust, Draped front sash accent, Bodycon mini-length silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor No Apologies Open Back Halter Dress in Black | Size: L

Smoke And Mirrors Strappy Back Mid Dress in Grey

$49.90

(6)

Own the moment in this sheer-meets-sculpted statement piece. With a draped cowl neckline, open strappy back, and ruched mesh that molds to your shape, this halter midi dress was made to steal glances. Fit & FeaturesAbstract print, mesh-lined fabric, moderate stretch, Plunge cowl halter neckline, Open strappy back detail, Bodycon fit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Smoke And Mirrors Strappy Back Mid Dress in Grey | Size: XL | Mesh Fabric

Windsor Desert Babe Abstract Cutout Mini Dress in Mauve

$36.90

(6)

Stand out in this abstract mesh mini dress with plenty of sexy details that turn heads! Designed to highlight your curves with a cutout bodycon fit and a daring side ruffle slit. Fit & FeaturesAbstract print, mesh fabric, stretchy knit lining, Cowl halter neckline, spaghetti strap tie, Cutout bodice, hoop insert, Side ruffled slit with tie, Bodycon silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Desert Babe Abstract Cutout Mini Dress in Mauve | Size: M | Knit Fabric/Mesh Fabric/Mesh Fabric

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.

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