Vacation Looks
Vacation dressing should be easy, stylish, and ready for wherever the day takes you. Start with mini sundresses and flirty rompers that work for both sightseeing and rooftop drinks at sunset. Add in flowy maxis, crochet cover-ups for poolside sunbathing, and sleek sunnies that instantly pull a look together. From cutoff denim shorts to swimwear with eye-catching details, these outfits keep your suitcase light and your style on point for every getaway moment.
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Vacation Dresses & Outfits for Effortless Getaways
Pack light and look luxe in vacay dresses and vacation outfits designed for sun-soaked escapes. Whether you’re poolside at a beach resort or exploring cobblestone streets, Windsor’s resortwear blends breezy fabrics, relaxed silhouettes, and bold prints for travel outfits you’ll want to wear on repeat.
Easy, Packable Styles
Slip into breezy maxi dresses in tropical prints or neutral tones—white, ivory, and tan—for instant cruisewear elegance. Chic rompers and vacay outfits like matching top-and-bottom sets in airy cotton or linen make packing a breeze and styling stress-free.
Day-to-Night Versatility
Transition from sunrise yoga to sunset cocktails in flowy sundresses or relaxed separates. Mix and match colorful vacation-ready separates—think high-waist shorts with off-shoulder tops—or choose effortless travel outfits in knit jumpsuits and wrap skirts that go anywhere.
Resort & Beach Essentials
Complete your look with stylish bikinis under sheer cover-up dresses or mesh tunics. Add slide sandals, statement sunglasses, and a woven tote for poolside chic. From beach days to rooftop lounges, these vacay dresses keep you feeling confident and carefree.
Ready to jet off in style? Explore Windsor’s full collection of vacation dresses and outfits online, in-app, or at your nearest Windsor store.
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Trendy Status Croc-Embossed Handbag
Showcase your trendy status with this chic croc-embossed handbag! Featuring an angled shape, a top handle design, and an included adjustable shoulder strap, this bag is perf for everyday wear. Style with statement earrings.
Fit & Features
- Angled shape
- Top handle design
- Magnetic button closure
- Removable adjustable shoulder strap
- Croc-embossed pattern
- Faux leather fabric
- Woven interior, single zippered pocket
Style Number/Barcode: 07204-0674
Category Name: Vacation Looks
Price: $4.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold Babe Halter Plunge Neck Romper
Perfect for a day or night out, this romper will make you stand out from the crowd with its flowy and flattering design. The halter plunge neck adds a touch of daring while the open back enhances your silhouette.
Fit & Features
- Knit fabric, stretchy knit shorts lining
- Plunge halter neckline, tie straps
- Open back
- Flowy mini skirt overlay
- Runs true to size
Style Number/Barcode: 06503-000064
Category Name: Vacation Looks
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fall Back On Block Heel Booties
This season, you'll be reaching for these sleek faux leather booties featuring a trendy square toe, block heel, side zipper closure, and fit above the ankle. Complete the look in a plaid coat for a PSL run!
Fit & Features
- Square toe
- Block heel
- Side zipper closure
- Above the ankle fit
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1558
Category Name: Vacation Looks
Price: $4.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simple Sleek Round Sunglasses
These simple sleek round sunglasses are perfect for an everyday chic look. They feature a metal frame with hexagon-shaped tinted lenses and thin metal arms. Style these shades with hoop earrings.
Fit & Features
- Metal frame
- Hexagon-shaped tinted lenses
- Rubber nose pads
- Thin metal arms
Style Number/Barcode: 07008-0957
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Take A Look Sweater Midi Dress
Let everyone take a look at you in this sweet sweater midi dress perfect for the autumn season! This dress features a sleeveless halter neck with tie closure, a bodycon silhouette, and a cutout waist with a front slit along the hem. Complete the look in pointy-toe booties.
Fit & Features
- Sleeveless halter neck with tie closure
- Bodycon silhouette
- Cutout waist, front slit
- Midi-length hem
- Rib-knit sweater fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1416
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Edgy Stunner Graphic T-Shirt Dress
Show off an edgy style with this on-trend graphic t-shirt dress! It features a crew neckline with a notched design with safety pin detailing, short sleeves, a mini-length, fitted silhouette, and a motorcycle and eagle graphic with the script "American Motorcycles Road Lifestyle 1974." Complete your 'fit with combat boots.
Fit & Features
- Crew neckline, notched design, safety pin detailing
- Short sleeves
- Mini-length hem, form-hugging fit
- Motorcycle and eagle graphic
- Script that reads, "American Motorcycles Road Lifestyle 1974"
- Cotton-blend fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1445
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Functional Style Denim Cargo Joggers
Functional fashion in a stylish utility design, these denim cargo joggers secure your must-haves while keeping your look edgy and cute! They feature a high-rise waist with a detachable good vibes keychain, a six-pocket styling, a jogger leg silhouette, and elasticized cuffs. Style with combat booties for a casual hang!
Fit & Features
- High-rise waist, detachable "Good Vibes" keychain
- Front button and hidden zipper closure
- Six-pocket styling, belt loops
- Jogger leg silhouette
- Elasticized cuffs
- Non-stretch denim fabric
- Runs true to size
Style Number/Barcode: 06302-0709
Category Name: Vacation Looks
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Simple Life Crew Tank Midi Dress
All a girl needs is this basic crew tank midi dress perfect for dressing up or down! It features a sleeveless bodice, wide tank shoulder straps, a midi-length hem, and a bodycon silhouette on lined ribbed knit fabric with plenty of stretch. Style this mid-length dress with a jacket and suede booties.
Fit & Features
- Sleeveless crew neckline
- Wide tank shoulder straps
- Midi-length hem
- Bodycon silhouette
- Lined ribbed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4772
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fall Florals Mesh Crop Bustier
This fall calls for this sweet floral mesh bustier you'll adore styling with your fave denim! It features an off-the-shoulder neckline with short sleeve cuffs, a ruched bust with padded cups, and a hidden front hook and eye closures leading to the cropped hem. Complete the look in new jeans for a pumpkin patch!
Fit & Features
- Off-the-shoulder neckline
- Ruched bust, padded cups
- Short sleeve cuffs
- Hidden front hook and eye closures
- Cropped hem
- Floral mesh fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4412
Category Name: Vacation Looks
Price: $7.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Effortless Everyday Ribbed Knit Midi Dress
Effortlessly chic for every day, this ribbed knit midi dress is a must-have for fall. It features a V-neckline, a combination of front spaghetti straps and long fitted sleeves, and a midi-length, curve-hugging silhouette. Style with ankle booties for coffee dates this season.
Fit & Features
- V-neckline
- Front spaghetti straps, long fitted sleeves
- Midi-length hem
- Fitted bodycon silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4975
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Autumn Chill Faux Wool Vest
Layer on this faux wool vest for a fashionably-chic look this autumn season. It features a sleeveless bodice, a lapel collar, an open front, hidden side pockets, and a relaxed fit. Style over a basic bodysuit and dress pants paired with ankle booties.
Fit & Features
- Sleeveless bodice
- Lapel collar
- Open front
- Hidden side pockets
- Relaxed silhouette
- Faux wool fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06201-0334
Category Name: Vacation Looks
Price: $18.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Shimmer Slouch Stiletto Boots
Shimmer and shine with every step in these slouch stiletto boots featuring a pointy toe, all-over rhinestone embellishments, under-the-knee length, and a side zipper closure on faux suede material. Complete the look in a sassy mini dress.
Fit & Features
- Slouched design
- Pointy toe
- Stiletto heel
- Rhinestone embellishments
- Under-the-knee length
- Side zipper closure
- Faux suede material
- Runs true to size
Style Number/Barcode: 07402-0847
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek And Stylish Moves Belted Pants
Step out and stun in these sleek and stylish pants! They feature a high-rise belted waist, front pockets, a skinny-leg silhouette, and a chic snake-embossed pattern. Pair with the matching crop top and clear heels.
Shop Matching Top: Sleek And Stylish Moves Crop Top
Fit & Features
- High-rise belted waist
- Hidden front zipper and button closure
- Front pockets
- Skinny-leg fitted silhouette
- Snake-embossed pattern
- Faux leather fabric, no stretch
- Runs true to size
Style Number/Barcode: 06402-0442
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sleek And Stylish Moves Crop Top
Step out and stun in this sleek and stylish crop top! It features a sleeveless square neckline, thin tank shoulder straps, a cropped, form-hugging fit, and a chic snake-embossed pattern. Pair with the matching belted pants and clear heels.
Shop Matching Bottoms: Sleek And Stylish Moves Belted Pants
Fit & Features
- Sleeveless square neckline
- Thin tank shoulder straps
- Back zipper, hook and eye closure
- Cropped hem, form-hugging fit
- Snake-embossed pattern
- Faux leather fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06003-1715
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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New Rules High Rise Boyfriend Jeans
Set the style scene for the new season in these high-rise boyfriend jeans you're sure to be wearing on rotation! They feature a trendy asymmetrical waist and a boyfriend-leg design on vintage-inspired medium-wash denim with color fading. Complete the look in a corset top and mules.
Fit & Features
- High-rise asymmetrical waist
- Boyfriend leg design
- Front buttons and hidden zipper closure
- Five-pocket styling, belt loop accents
- Medium wash denim, color fading
- Minimal stretch
- Runs true to size
Style Number/Barcode: 06602-0398
Category Name: Vacation Looks
Price: $20.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Under The Sun Straw Buckle Slide Sandals
A pair of straw buckle strap sandals you'll reach for every sun shining day!
Fit & Features
- Round toe
- Dual straw buckle straps
- Comfortable footbed
- Traction bottom
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1290
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Side Ties Turtleneck Sweater Top
Your new favorite sweater top for wearing on those brisk autumn days! The sleeveless tank top features a turtleneck, cutout sides with tie closures, and a cropped hem on rib-knit fabric. Complete the look in flare pants and heels.
Fit & Features
- Sleeveless
- Turtleneck
- Cutout sides with tie closures
- Cropped hem
- Sweater rib-knit fabric
- Fits true to size
Style Number/Barcode: 06005-1121
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Set A Trend Crepe Slit Midi Skirt
Set a trend by walking in wearing this crepe midi skirt for your weekend plans! It features a sleek high-rise waist, form-hugging fit and a sultry side slit perfect for styling with chic stiletto heels.
Fit & Features
- High-rise waist
- Form-hugging fit
- Side slit
- Midi-length
- Crepe fabric
- Fits true to size
Style Number/Barcode: 06501-0725
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Taylor High Rise Skinny Crop Jeans By Windsor Denim
Achieve an hourglass appearance in the Taylor High Rise Jeans by Windsor Denim! Put your curves on display in her flattering high-rise waist, skinny-leg design with a raw hem and light distressed accents. The jeans are composed of a Lycra-cotton blend denim fabric with stretch and shape retention. Complete the look in a chic top and heels.
Fit & Features
- High-rise waist
- Light distressed accents
- Skinny-leg design, raw crop hem
- Front button and hidden zipper closure
- 5-pocket styling, belt loops
- Lycra-cotton blend denim, minimal stretch
- Fits true to size
Style Number/Barcode: 06602-0338
Category Name: Vacation Looks
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chain My Mind Side Slit Midi Dress
This knit midi dress will change your mind about going out for the night! Catch all the attention in this sultry dress featuring a sleeveless square neck, chain link adjustable spaghetti straps, a bodycon silhouette, and a side slit. Complete the look with a bold clutch purse.
Fit & Features
- Sleeveless square neck
- Chain link adjustable spaghetti straps
- Bodycon silhouette
- Side slit
- Midi-length hem
- Slinky knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4800
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Catch My Glam Rhine Layer Necklace
Add this glam necklace to elevate your outfit! It features a four-layered design, one snake chain, one rhinestone chain, and one chain link with clear stone charms and a lobster clasp closure. Complete the look in a sleek midi dress for wine night.
Fit & Features
- Four-layered design
- One snake chain
- One rhinestone chain
- One chain link with clear stone charms
- Lobster clasp closure
Style Number/Barcode: 07002-1280
Category Name: Vacation Looks
Price: $2.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feeling Fierce Leopard Midi Skirt
Your wardrobe can't be tamed with the addition of this leopard midi skirt ready for a night on the prowl! Show your wild side in this high-rise skirt featuring a back zipper closure, a curve-hugging silhouette, and a high-cut front slit, composed of crepe chiffon-lined woven fabric. Complete the look in a twist crop top and strappy heels.
Fit & Features
- High-rise waist
- Back zipper closure
- Curve-hugging silhouette
- High-cut front slit, midi-length hem
- Leopard print
- Crepe chiffon fabric, lined, no stretch
- Fits true to size
Style Number/Barcode: 06401-0467
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Take A Trip Sweater Halter Dress
Taking a trip somewhere fab? You're gonna need this sweater halter dress perfect for looking chic on the go! It features a sleeveless bodice, cross straps with neck-tie closure, a bodycon silhouette, and a mini-length hem. Complete the look in linear earrings.
Shop More Styles: The Sweater Collection
Fit & Features
- Sleeveless halter neck
- Cross straps, neck-tie closure
- Bodycon silhouette
- Mini-length hem
- Rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1605
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Head Over Heels Cutout Jumpsuit
Watch everyone fall head over heels for you in this cutout jumpsuit perfect for your next wine night! It features a sleeveless halter neckline, a cutout bust and waist accent, a partial open-back, and a flared hem. Complete the look in earrings.
Fit & Features
- Sleeveless halter neckline
- Cutout bust and waist accent
- Partial open-back
- Flared hem
- Knit fabric
- Fits true to size
Style Number/Barcode: 06502-1446
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance