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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Mesh Game Bikini Top
Bring that mesh game poolside in this frilly bikini top! It features narrow shoulder straps with ruffle details, and padded triangle cups. Bikini top ties at the back and is composed of a stretchy mesh fabric. Pair with matching bottom to complete this mesh-y look!Model is 5'9 with a 32" bust, 24" waist and 36" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07104-0138
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bathing Baddie V Wire Swim Top
You're too bad for a typical bikini! Your styles calls for this neon green swim top with padded V wire cups and contrast black shoulder straps. Don't forget the matching caged swim bottom!Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07104-0015
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glow On Swim Top
Glow on bby in this bold neon swim top! It features classic triangle cups, wide shoulder straps with knotted accents and a tie back accent. Be sure to pick up the matching bottoms to complete your look!Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07104-0012
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On The Edge Sunglasses
Stay on the cutting edge of style with these chic sunnies! They feature a slim browbar accent, brown hued cat-eye lenses, nose pads and slim arms.
Style Number/Barcode: 07008-0569
Category Name: Vacation Looks
Price: $3.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wrap Around Revo Shield Sunglasses
Shield away unwanted rays with this sporty sunnies! They feature a wrap around design with large reflective lenses and a partial black frame.
Style Number/Barcode: 07008-0678
Category Name: Vacation Looks
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keep It Undercover Sunglasses
Keep it undercover with these sleek cat eye shades! They feature a metal frame and black angled cat eye lenses.
Style Number/Barcode: 07008-0675
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Fashionista Sunglasses
Yes fashionista, rock these cute circular shades! They feature a gold metal frame, circular lenses, and mirrored green tinted lenses.
Style Number/Barcode: 07008-0667
Category Name: Vacation Looks
Price: $3.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Heart Cat Eye Sunglasses
You'll have major heart eyes for these fab cat eye sunnies! They feature an angled heart shaped white plastic frame with black tinted lenses. Offer 100% UV protection.
Style Number/Barcode: 07008-0660
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Major Fashionista Sunglasses
Yes fashionista, rock these cute circular shades! They feature a metal frame, circular lenses, and dark tinted lenses.
Style Number/Barcode: 07008-0668
Category Name: Vacation Looks
Price: $3.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect Day High-Rise Straight Leg Denim Jeans
It's always a perfect day in these straight-leg denim jeans with a flattering high-rise waist perfect for crop tops or sweaters.
Fit & Features
- Denim fabric
- High-rise waist
- Straight-leg fit
- Front button closure
- Front pockets, belt loops
- Runs true to size
Style Number/Barcode: 06602-0557
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Geometric Rimless Sunglasses
We're raving about these trendy, retro black sunnies! They feature a geometric cat eye design with rimless lenses.
Style Number/Barcode: 07008-0601
Category Name: Vacation Looks
Price: $4.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Mini Rectangle Sunglasses
Take a peek into the past with these retro inspired sunglasses! They feature a thin, metallic gold frame, and dark square lenses.
Style Number/Barcode: 07008-0600
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Effortlessly Edgy Cat Eye Sunglasses
Add an effortless edge to your look with these sleek sunglasses! They feature an angled cat eye design with a rose gold metal trim and black lenses.
Style Number/Barcode: 07008-0595
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Squared And Fab Sunglasses
Let these sunnies make a statement for you! They feature a hard plastic square frame, dark tinted lenses and wide arms.
Style Number/Barcode: 07008-0593
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glam Gal Cat Eye Sunglasses
Girl, you'll look oh so glamorous in these flashy cat eye sunnies! The pink sunglasses feature a metal cat eye frame with small cut outs, gemstone accents on the sides, and pink tinted lenses.
Style Number/Barcode: 07008-0591
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Edgy Thin Cat Eye Sunglasses
Keep it trendy in these sleek black sunglasses. They feature a thin cat eye frame with dark lenses.
Style Number/Barcode: 07008-0587
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Studded Trim Cat Eye Sunglasses
These studded trim cat eye black sunnies will give your look a trendy touch! They feature a cat eye frame with tiny gold stud detailing with plastic arms and dark lenses.
Style Number/Barcode: 07008-0568
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dazzle Diva Cat Eye Sunglasses
Get ready for your close up with these fashionista-worthy sunnies! They feature a tortoise shell hard plastic frame, tinted cat eye lens and mini rhinestone accents at the corners.
Style Number/Barcode: 07008-0490
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Studded Brow Bar Sunglasses
Update your sunnies game with this must have pair in black! They feature a straight brow bar accented with small silver studs, large square-like frames, and black plastic arms.
Style Number/Barcode: 07008-0548
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Livin' Large Shield Sunglasses
These large shield sunglasses shows everyone who's boss! They feature a flat top, large shield lenses, and a plastic frame.
Style Number/Barcode: 07008-0543
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Color Me Block Sunglasses
Block out the sun and the haters in these large color block sunglasses. They feature large round frames with black tinted lenses and large plastic arms with a multi color design.
Style Number/Barcode: 07008-0546
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Out Of This World Sunglasses
Look like an out of this world beauty with these trendy sunnies! They feature a square design with a brow bar, nose pads, and purple ocean lenses. Offer 100% UV protection.
Style Number/Barcode: 07008-0535
Category Name: Vacation Looks
Price: $2.73 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On The Move Flat Top Sunglasses
Move through your day in these stylish shades! They feature a flat rimless top, large square shaped lenses, nose pads, dark tinted lenses with an ombre detail and narrow arms.
Style Number/Barcode: 07008-0524
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bohemian Chic Sheer Lace Flare Pants
So boho chic, these sheer lace flare pants are a style staple for festival season. Show off your curves with the hip-hugging fit that continues through the leg to the trendy flared hem.
Shop Matching Black Top: Bohemian Chic Sheer Lace Tie-Front Top
Fit & Features
- Sheer floral lace fabric with knit panty lining, high stretch
- High-rise elasticized waist
- Hip-hugging fit
- Form-hugging fit through the leg
- Flared hem
- Pants in size small have a 9" front rise with a 35" inseam
- Runs true to size
Style Number/Barcode: 06502-2582
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free