Cool Weather Dresses

Cool weather dresses are your secret weapon for slaying those chilly days with style and sass. When the temperature drops, it's time to layer up without sacrificing an ounce of fabulousness. Picture yourself wrapped in cozy chicness, whether you're strutting down city streets or sipping cocoa by the fire. These dresses are here to keep you warm and on-trend, offering versatility that pairs perfectly with your favorite boots and jackets. So, grab your pumpkin spice latte and let's make some unforgettable cool weather memories!

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$39.90

4.7 star rating

A brown knit midi dress with long sleeves, off-the-shoulder neckline, and ruched bodycon fit.

$54.90

5 star rating

A black ribbed knit midi dress featuring a tie-dye pattern, scoop neckline, and back slit.

$44.90

5 star rating

A grey ribbed knit midi dress with a sweetheart neckline and twist accent, perfect for casual outings.

Sale

$9.97 $38.90 74% off

5 star rating

A brown knit bodycon midi dress with flare cuff sleeves and a stylish V-neckline.

$39.90

5 star rating

A natural striped knit mini dress featuring a flirty cutout back and bodycon fit.

$36.90

A natural rib knit mini dress with a folded off-the-shoulder neckline and flattering skater silhouette.

Best Seller

$36.90

4.621212 star rating

An elegant sage off-the-shoulder midi dress with a bodycon fit and flared hem.

Best Seller

$44.90

4.571429 star rating

A sophisticated white midi dress with chiffon sleeves, a square neckline, and a ruched bodycon silhouette.

$48.90

4.875 star rating

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

$35.90

4.666667 star rating

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

$46.90

5 star rating

A black floral midi dress with a corset bodice, sweetheart neckline, and flirty front slit.

$42.90

5 star rating

A black ponte mini dress with sheer chiffon sleeves and a playful square neckline.

Sale

$9.97 $39.90 75% off

5 star rating

A black mini dress with a cutout bust, ruched wrap design, and sheer mesh long sleeves.

$49.90

3.5 star rating

A white cold shoulder midi dress featuring a bodycon silhouette with ruched seams and padded cups.

Sale

$9.97 $44.90 78% off

5 star rating

A black velvet floral mini dress with sheer sleeves and a sweetheart neckline for holiday events.

$42.90

3.5 star rating

An abstract print maxi dress with a ruched bodycon silhouette and sheer off-the-shoulder sleeves.

Sale

$21.97 $42.90 49% off

5 star rating

A brown ribbed knit mini dress with a scoop neckline and faux topper long sleeves.

$59.90

5 star rating

An ivory A-line maxi dress with gauze fabric, sheer lace insets, and a faux leather belt.

$42.90

5 star rating

A black ribbed knit bodycon mini dress with trendy cutouts and lattice accents for a chic look.

Sale

$22.97 $49.90 54% off

5 star rating

A light blue chiffon midi dress with puff sleeves, floral print, and a chic high front slit.

$36.90

5 star rating

A cozy heather grey ribbed knit mini dress with an off-the-shoulder neckline and A-line silhouette.

$29.90

5 star rating

A trendy brown striped knit mini dress with a mock neckline and long fitted sleeves.

$38.90

A burgundy knit skater dress featuring a cold-shoulder design and corset-style seams for a sleek look.

$38.90

An olive knit midi dress featuring an off-the-shoulder neckline, ruching, and a high back slit.

$59.90

A green velvet mermaid dress with ruching, adjustable straps, and a high front slit.

$32.90

A cozy ivory mini dress with a striped ribbed knit, off-the-shoulder design, and A-line silhouette.

$54.90

An ivory floral chiffon skater dress featuring sheer long sleeves, a sweetheart neckline, and button accents.

Sale

$9.97 $38.90 74% off

A wine velvet mini dress with a sweetheart neckline, flare sleeves, and a bodycon silhouette.

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Marissa Formal Satin Cowl Neck Dress in Green
(162) 4.5740743 star rating

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

Leila Sequin Bodycon Mini Dress in Royal Blue
(138) 4.7028985 star rating

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

Senorita Mesh Strappy Mini Dress in Red
(81) 4.580247 star rating

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

Windsor Exceptional Off-The-Shoulder Flared Midi Dress in Natural
(66) 4.621212 star rating

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

Cute Attitude Ponte Slit Mini Skort in Black
(63) 4.7619047 star rating

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

Windsor Brynlee Sequin Embroidered Bodycon Dress in Sage
(56) 4.589286 star rating

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

Windsor Keira Faux Pearl Strappy Open-Back Mini Dress in Light Blue-2
(53) 4.773585 star rating

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

Get Down With Basic Slit Mini Skirt in Black
(52) 4.1346154 star rating

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

See Me Shining Glitter Off-The-Shoulder Mini Dress in Wine
(49) 4.5102043 star rating

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

Kristen Faux Pearl Mini Party Dress in White
(46) 4.695652 star rating

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

Cool Weather Dresses

When the air gets a little crisp and your iced coffee order turns into a hot latte, it’s officially time to switch up your style game and bring out those cool weather dresses that make every day feel like a main character moment. These aren’t just dresses—they’re your armor against chilly breezes and your ticket to looking effortlessly put-together, no matter what’s on your calendar. Whether you’re heading to a movie night with your besties, meeting up for a cozy brunch, or just taking a stroll through the city, the right cool weather dress lets you dress for the vibe and the forecast. Think of those soft, sweater-knit fabrics that hug you in all the right places, long sleeves that bring a little drama, and flirty hemlines that make layering a total breeze. Add a pair of boots, toss on a faux leather jacket, and suddenly you’re serving looks that are as warm as they are fire. These dresses are designed for anyone who loves to stay cute when the temperature dips—students hustling across campus, boss babes making power moves at work, or even your little sister who just wants to feel grown-up at family dinners.

Gift-wise, cool weather dresses are the ultimate “I get you” present. Picture this: your BFF’s birthday is coming up and you want to give her something she’ll actually wear more than once. A cozy-chic dress is a total win—she’ll think of you every time she slips it on for a coffee run or a spontaneous road trip. Or maybe you’ve got a cousin who’s always cold but refuses to sacrifice style; a long-sleeve knit dress is basically a warm hug in outfit form. These dresses are also perfect for those “nothing to wear” emergencies, making them a must-have for anyone who likes to keep their closet ready for anything. Layer them up with tights and scarves for extra warmth, or keep it simple with statement earrings and a swipe of bold lipstick when you want your look to do all the talking. And let’s be real—there’s something magical about slipping into a dress that’s both cute and comfy, especially when you’re racing out the door but still want to look like you tried (even if you hit snooze three times).

When you’re ready to level up your wardrobe for the cooler months, pay attention to the little details that make a big impact—think ribbed textures that add dimension, mock necklines that bring the drama, and waist ties that let you cinch it just how you like. These are the pieces that make you feel unstoppable, whether you’re strutting into a meeting or twirling on the dance floor at a friend’s party. If you’re obsessed with versatility, you’ll love how these dresses can go from chill to glam with just a few accessory swaps. And if you’re looking to expand your collection, don’t miss our curated selection of Winter Casual Dresses—it’s basically a treasure trove for anyone who wants to slay the style game no matter the forecast. So go ahead, treat yourself (or your ride-or-die) to a dress that brings the heat when the temps drop. You deserve to feel as bold and unstoppable as you look, every single day.

Top Picks For Cool Weather Dresses