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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Casual-Cozy Long Line Plaid Shacket
Layer on this casual-cozy shacket for an effortlessly stylish look! It features a collared neckline, long sleeves, a complete button-down front, hidden side pockets, and a long line silhouette with a relaxed fit. Wear this shacket with ankle booties.
Fit & Features
- Collared neckline
- Long sleeves, double button details
- Button-down front
- Hidden side pockets
- Long line silhouette, relaxed fit
- Woven fabric, no stretch, plaid print
- Runs true to size
Style Number/Barcode: 06204-1257
Category Name: Vacation Looks
Price: $19.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cozy Plush Plaid Scarf
Cozy on up in this plush woven scarf that will go with your everyday winter looks. It features a cute plaid print with neutral tones, fringe detailing at the hems, and an oversized blanket fit. Style this soft woven scarf with a sweater dress and booties.
Fit & Features
- Plaid print
- Neutral tones
- Fringe detailing
- Oversized blanket fit
- Woven fabric, no stretch
Style Number/Barcode: 07305-0365
Category Name: Vacation Looks
Price: $2.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chill Out Plaid Shacket
Chill out in a cozy shacket to layer over your looks this season! The shacket features a collared neckline, a multi-button down front, two chest pockets, long sleeves, and a long line length. The shacket is composed of a brushed faux wool fabric that offers a relaxed fit with minimal stretch. Complete look with distressed jeans and ankle booties.
Fit & Features
- Collared neckline
- Multi-button down front
- Two chest pockets
- Long sleeves
- Longline length, plaid print
- Faux wool fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06204-1278
Category Name: Vacation Looks
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rhinestone And Pearl Luxe Knit Beanie
Bring the luxe with a beanie that adds that sparkling touch to your outfit. The beanie features a knit body, faux pearl accents, rhinestones, and a faux fur pom pom accent. Complete look with a sweater and high waist jeans.
Fit & Features
- Knit material
- Faux pearl accents
- Rhinestones
- Faux fur pom pom accent
Style Number/Barcode: 07302-0391
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keep It Chic And Cozy Blanket Scarf
Keep your look chic and cozy bundled up in this woven scarf! It features a checkered print with neutral tones, fringe detailing at the hems, and an oversized blanket fit. Style this soft scarf with a faux leather jacket and booties.
Fit & Features
- Checkered print
- Neutral tones
- Fringe detailing
- Oversized blanket fit
- Woven fabric, no stretch
Style Number/Barcode: 07305-0366
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feeling Wild Leopard Knit Vest
Channel your wild side with a vest that can be layered over your favorite long sleeve tops. The vest features a trendy leopard print, a sleeveless V-neckline, and a ribbed hem. The vest is composed of a soft-to-the-touch knit fabric that offers a relaxed fit with a moderate stretch. Complete look with combat boots.
Fit & Features
- Sleeveless V-neckline
- Leopard print
- Ribbed hem
- Knit fabric
- Relaxed fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1110
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fashion Puff Quilted Stiletto Booties
The perfect puff stiletto bootie every fashionista needs! They feature a pointed toe, quilt pattern, and a cinched ankle with a self-tie. Complete your look with edgy joggers.
Fit & Features
- Pointed toe
- Quilt pattern
- Stiletto heel
- Cinched ankle, self-tie
- Faux leather
- Runs true to size
Style Number/Barcode: 07403-1315
Category Name: Vacation Looks
Price: $12.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On The Edge Trendy Lug Sole Bootie
Take your style to the edge in this lug sole bootie featuring a round toe, block heel, on faux leather material. It features elasticized inserts for easy on/off styling. Complete your look with a trench coat and jeans.
Fit & Features
- Round toe
- Block heel
- Elasticized side inserts for easy on/off styling
- Lug sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1337
Category Name: Vacation Looks
Price: $12.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Chelsea Lug Sole Booties
The classic Chelsea bootie in a trendy lug sole! This bootie features a round toe design, block heel, and elasticized inserts for easy on/off styling on a faux suede material. Complete your edgy-chic look with distressed jeans.
Fit & Features
- Round-toe design
- Block heel
- Elasticized inserts for easy on/off styling
- Lug sole
- Faux suede material
- Runs true to size
Style Number/Barcode: 07403-1338
Category Name: Vacation Looks
Price: $12.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On Vacay V-Neck Floral Maxi Dress
Look a daydream come true in this floral maxi dress while on vacay! Designed with a bold floral print on a sultry form-hugging silhouette.
Fit & Features
- Floral print, mesh-lined fabric
- V-neckline
- Spaghetti straps
- Form-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-4076
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tough Chic Lug Sole Booties
Edge up your everyday look in this lug sole bootie! It's designed with an almond toe, block heel, and elasticized inserts for easy on/off styling. The bootie is composed of faux leather material. Complete the look in joggers.
Fit & Features
- Almond toe
- Block heel
- Elasticized inserts for easy on/off styling
- Lug sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1327
Category Name: Vacation Looks
Price: $12.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Trendy Glam Chain Detail Panama Hat
Bring the trendy glam vibes to your everyday look with this faux wool Panama hat. It features a wide flat brim with a center chunky chain-link accent trim. Pair this hat with basic hoop earrings.
Fit & Features
- Wide flat brim
- Chunky chain-link trim
- Faux wool material
Style Number/Barcode: 07302-0425
Category Name: Vacation Looks
Price: $7.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glam Swag Rhinestone Layered Necklace
Showcase your edgy-glam style in this layered necklace! It features two layers including a chain-link and rhinestone drop on a dainty chain. Compliment your look with a chic bodysuit.
Fit & Features
- Two layers
- One chain-link
- One dainty chain with rhinestone drop
- Lobster clasp closure
Style Number/Barcode: 07002-1031
Category Name: Vacation Looks
Price: $2.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bold Moment Faux Wool Panama Hat
Create a bold moment with a hat that answers the call for adventure, babe! The hat features a traditional Panama design, a trendy ribbon around the brim, and is composed of a faux wool material. Complete look with a babydoll dress and ankle booties for those bohemian vibes.
Fit & Features
- Traditional Panama design
- Ribbon trim
- Faux wool material
Style Number/Barcode: 07302-0383
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Western Vibes Faux Leather Boots
Home on the range in style wearing these faux leather boots! They feature a pointed toe, block heel, zipper closure, and smooth, faux leather exterior. Perfect for styling with skinny jeans.
Fit & Features
- Pointed toe
- Block heel
- Zipper closure
- Knee-high length
- Faux leather exterior
- Runs true to size
Style Number/Barcode: 07402-0322
Category Name: Vacation Looks
Price: $12.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Just My Type Knee-High Boots
Your outfit of the day isn't complete without these knee-high boots! They feature a pointed toe, block heel, zipper closure, and smooth, faux leather exterior. Perfect for styling with a denim jacket.
Fit & Features
- Pointed toe
- Block heel
- Zipper closure
- Knee-high length
- Smooth faux leather exterior
- Runs true to size
Style Number/Barcode: 07402-0320
Category Name: Vacation Looks
Price: $12.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Does It Faux Fur Slippers
These faux fur slippers are total lounge goals! They feature double bands and a traction bottom. Perfect for styling with a cardigan.
Fit & Features
- Double bands
- Faux fur
- Traction bottom
- Runs true to size
Style Number/Barcode: 07408-0083
Category Name: Vacation Looks
Price: $9.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lazy Day Faux Sherpa Sandals
Treat your feet to a day off with these cozy sandals! They feature ultra-soft faux sherpa and a traction bottom. Complete your look with leggings.
Fit & Features
- Faux sherpa
- Ultra-soft footbed
- Traction sole
- Runs true to size
Style Number/Barcode: 07408-0086
Category Name: Vacation Looks
Price: $9.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Forever Cozy Slippers
Treat your feet in cozy style with faux fur slippers! They feature double bands and a traction bottom with an ultra-soft sole. Style with a cozy loungewear set.
Fit & Features
- Double bands
- Faux fur
- Traction bottom
- Runs true to size
Style Number/Barcode: 07408-0085
Category Name: Vacation Looks
Price: $9.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual And Cozy Chenille Sweater
This adorable chenille knit sweater is casually chic and oh-so-cozy! It features a ribbed turtleneck, long dolman-style sleeves with cuffed hems, button detailing down the sides, and an oversized, relaxed fit. Pair this sweater with faux leather pants and booties.
Fit & Features
- Ribbed turtleneck
- Long dolman sleeves, cuffed hems
- Buttons down the sides
- Chenille knit fabric
- Oversized fit
Style Number/Barcode: 06005-1073
Category Name: Vacation Looks
Price: $15.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sleek N' Chic Hoop Earrings
Keep it chick with these classic, pink hoop earrings! The hoops have a sleek design that feature a rose gold shine an feature both an omega and post back closure for security.
Style Number/Barcode: 07001-4042
Category Name: Vacation Looks
Price: $2.97 $5.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bohemian Chic Chandelier Rhinestone Earrings
Bring the chic factor to your look with earrings that wow! The earrings feature a multi-row chevron design, mini rhinestones, and a drop coin design. Complete look with a bustier and mini skirt.
Fit & Features
- Multi-row chevron design
- Mini rhinestones
- Drop coin design
- Fish hook back
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.Style Number/Barcode: 07001-0936
Category Name: Vacation Looks
Price: $2.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Vibes Leopard Print Cardigan
Layer on the cozy vibes with this trendy leopard print cardigan. It features long sleeves, an open front, ribbed hems, and a relaxed and comfortable fit. The fuzzy knit fabric offers a moderate stretch. Style this cardigan with a basic tee and dark wash denim.
Fit & Features
- Long sleeves
- Open front
- Ribbed hems
- Relaxed fit
- Leopard print
- Fuzzy knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1178
Category Name: Vacation Looks
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Covetable Charm Strapless Mini Skater Dress
From casual outings to chic occasions, this strapless skater dress is one you'll covet for charming looks every time! The non-slip grip lining along the strapless neckline ensures a secure fit while the ruched bodycon bodice flatters your figure. The skater silhouette and pleated short-length hem add a playful touch to this poplin dress! Complete the look in sandals and sunnies.
Fit & Features
- Poplin stretchy fabric, sewn-in knit lining
- Back zipper and hook-eye closure
- Strapless square neckline
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3079
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free