Dresses For Winter Vacation
Dresses for Winter Vacation are all about balancing cozy comfort with serious style points—because your getaway deserves more than just a suitcase full of sweaters. Whether you’re jetting off to snowy mountain towns or chasing a little winter sun, the right dress makes packing (and outfit planning) so much easier. Think layers you can play with, textures that pop in every pic, and silhouettes that feel as effortless as vacation should. Wherever your winter escape takes you, these picks are ready to turn every moment into a style moment—no overthinking required.
$32 $45.90 30% off
A red brown knit midi dress featuring a halter neckline, open back, bodycon fit, and slit accent.
$54.90
A black velvet midi dress featuring a flocked floral pattern, cold-shoulder design, and ruched details.
$18.97 $42.90 56% off
A brown floral abstract maxi dress featuring daring cutouts, hardware trim, and a curve-hugging silhouette.
$19.97 $59.90 67% off
A black velvet formal dress featuring a one-shoulder neckline, wired V-neck, and high side slit.
$38.90
A white sleeveless ribbed knit midi dress featuring a V-neckline and chic high front slit.
$59.90
A brown chiffon maxi dress featuring cascading ruffles, sultry cutouts, and a flowy, slit silhouette.
$74.90
An ivory floral velvet bodycon dress with a cowl neckline and high side slit for elegance.
$69.90
A romantic wine-colored skater dress in jacquard woven fabric with an elegant off-the-shoulder neckline.
$42.90
A blue chiffon mini dress featuring a floral print, rhinestone embellishments, and an open tie-back halter neckline.
$18.97 $29.90 37% off
An olive green cable knit midi dress with a mock neck, form-hugging fit, and side slit.
$14.97 $54.90 73% off
A navy blue velvet midi dress featuring a one-shoulder neckline, bodycon fit, and front slit.
$69.90
A black glitter skater dress featuring an off-the-shoulder bow neckline and structured corset bodice.
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Achieve a perfectly stylish everyday look with this sleeveless ribbed knit midi dress! Designed with a comfortable ribbed knit fabric offering plenty of stretch, it features a V-neckline, spaghetti straps, a midi-length hem with a chic high front slit, and a form-hugging silhouette. Pair with a cropped denim jacket and clear mules. Fit & FeaturesStretchy ribbed knit fabric, V-neckline, Spaghetti straps, High front slit, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Perfectly Stylish Sleeveless Ribbed Knit Midi Dress in White | Size: L | Knit Fabric
Show off your smooth moves in this strapless bodycon midi dress perfect for dressing up or down for any occasion! Fit & FeaturesRib knit fabric, sewn-in knit lining, moderate stretch, Strapless neckline, Side slit, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Smooth Talker Strapless Bodycon Midi Dress in Brown | Size: XS | Knit Fabric
Sleek, soft, and made to flatter. This mock neck midi dress hugs in all the right places with side ruching and a soft modal blend knit fabric that gives casual polish. Perfect for weekday styling and weekend looks! Fit & FeaturesSoft modal-blend knit fabric, knit lining, moderate stretch, Sleeveless mock neck, Side ruched seams, Bodycon fit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Curve Flow Bodycon Midi Dress in Black | Size: XS | Knit Fabric
Flirty, fitted, and effortlessly classic. This halter midi dress features a plunging neckline and all-over polka dot print for that perfect mix of vintage charm and modern polish. Perfect for brunch, celebrations, or date night! Fit & FeaturesPolka dot print, mesh-lined fabric, moderate stretch, Halter V-neckline, Curve-hugging fit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Retro Romance Halter Midi Dress in Black | Size: S
Windsor Moonlit Bloom Abstract Floral Maxi Dress in Brown
$35 $49.90
30% off
Slip into something sleek—this mesh maxi dress flaunts an abstract floral print that gives the illusion of an hourglass figure for an effortless allure at every event you're seen at! Fit & FeaturesAbstract floral print, mesh-lined stretch fabric, Scoop neckline, Spaghetti straps, Curve-hugging silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Moonlit Bloom Abstract Floral Maxi Dress in Brown | Size: XS | Mesh Fabric
Giving flirty fairytale but make it chic. This lace-trimmed maxi dress hugs like a dream and serves up soft-girl glam with a sultry high side slit. Perfect for garden parties, shower celebrations, and dressy dates. Fit & FeaturesFloral print, mesh-lined fabric, Lace sweetheart neckline and shoulder straps, Back zipper closure, High side slit, Form-hugging silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Garden Party Chic Lace Floral Maxi Dress in Natural | Size: M
Show off pretty vibes in this adorable layered skater dress made with breezy eyelet knit fabric. Pair with sneakers for a cute casual look or wedges for a dressier style. Fit & FeaturesStretchy sheer eyelet knit fabric, partial knit lining, Square neckline, Spaghetti straps, Double-layered skater skirt, Short fit-and-flare silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Pretty Vibes Eyelet Knit Layered Skater Dress in White-2 | Size: L | Knit Fabric
Sun goddess maxi dress boasting a V-neckline with a unique metal accent and a body-skimming silhouette. Style with strappy sandals for a sunset dinner. Fit & FeaturesTextured knit fabric, soft knit stretchy lining, V-neckline with metal accent, Spaghetti straps, Body-skimming silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Into The Sun V-Neck Maxi Dress in Natural | Size: M | Knit Fabric
Show off a sleek fit in this chic smooth knit maxi dress featuring a strapless neckline and high-cut side slit. The form-hugging silhouette will flaunt your gorgeous figure. Fit & FeaturesSmooth knit fabric, high stretch, Strapless straight neckline, Ruched high front slit, Maxi-length hem, Form-hugging silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Fit Strapless High Slit Maxi Dress in Red | Size: XL | Knit Fabric
Soft curves, no effort. This ribbed knit midi dress hugs just right with a bodycon fit that moves from dinner plans to late-night photos without missing a beat. Fit & FeaturesSoft rib knit fabric, sewn-in stretch lining, Sweetheart neckline with twisted bust detail, Spaghetti straps, Fitted bodice through the waist, Bodycon silhouette through the hips, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Soft Focus Moment Ribbed Knit Midi Dress in Pink | Size: S | Knit Fabric