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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Leanna My Sunshine Floral Dress
Special OccasionLeanna simply radiates and you'll be the light at your next special occasion! She features a plunging neckline, adjustable narrow straps that create an X back, pleating in the bodice, and a high waist band. Skirt has a flowy, A-line silhouette for an ethereal and romantic look. Leanna has a knit short skirt lining and is comopsed of a semi-sheer floral chiffon fabric with no stretch. She includes an exposed back zipper closure.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-6769
Category Name: Vacation Looks
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bea Formal Floral Wrap Dress
Special OccasionRadiate a charming look as you let your beauty bloom in our gorgeous Bea dress! She features a sleeveless bodice, a plunging V neckline with an unlined mesh inset, padded cups and a double row of adjustable narrow straps. Her slim fit bodice leads to a sweeping floor length wrap skirt with pleated details and a high side slit that reveals a contrast satin-like lining. The all over floral print features white with blue hues. Dress is composed of a lined chiffon fabric that offers a form hugging fit with minimal stretch.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-6550
Category Name: Vacation Looks
Price: $19.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Zara Formal Rose Chiffon Dress
Special OccasionCreate a twirl worthy moment in our enchanting Summer dress! She features a plunging wrap V neckline, adjustable narrow straps, an open back design and a pretty tie-waist belt. Her slim fit bodice leads to a sweeping floor length silhouette to grace each step. Her over floral print pattern features a pretty blue hue. Dress is lined with a smooth knit fabric and includes an additional mini skirt length knit lining. Garment is composed of a lined sheer chiffon fabric that offers a relaxed fit with minimal stretch.
Model is 5'9" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-6342
Category Name: Vacation Looks
Price: $29.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Janine Floral Chiffon High Low Dress
Special OccasionLook as beautiful and delicate as a rose in our lovely Zara dress! She features a floral print on an ivory background, a plunging wrap V neckline and adjustable spaghetti straps. Her slim fit bodice leads to an elongating floor length, high-low, wrap-like skirt. Dress is composed of a partially lined chiffon fabric. Dress offers a relaxed fit with minimal stretch. Includes a back zipper.
Model is 5'8 with a 33" bust, 24" waist and 35" hips. She is wearing a size small.Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-6522
Category Name: Vacation Looks
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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True Colors Snake Print Scrunchie
Show your devious side with this sly, tan scrunchie! The hair tie has a classic scrunchie design paired with a faux scarf tie for the perfect wrap appearance. The hair tie features a smooth bunched fabric that has a trendy snake print you can't live without!
Style Number/Barcode: 07006-0885
Category Name: Vacation Looks
Price: $8.87 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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So Extra Rhinestone Hoops
Go for extra shine in these larger than life hoop earrings! They feature a gold hued large hoop adorned with rhinestones and an omega back closure.
Style Number/Barcode: 07001-4308
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Luxe Rhinestone Thin Belt
Create a luxe look with this rhinestone thin belt! It features a black hued faux leather thin belt embellished with small silver rhinestones on the exterior and buckle.Style Number/Barcode: 07301-1023
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Henny In My Cap
You've got Henny in your cup and you don't give AF it's on your cap, too! This black hat features an adjustable back strap, and a white "Henny" script on the front paired with a yellow leaf border.
Style Number/Barcode: 07302-1204
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Scalloped Lace Bodysuit
This scalloped lace bodysuit is perfect for the spring season! It features a sleeveless bodice, adjustable spaghetti straps that cross in the back, a low scoop back, a deep V scalloped neckline, and a thong bottom with snap button closures. The bodysuit is composed of a stretchy knit and floral lace fabric.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-8664
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All The Vibes Leopard Lace Long Tunic
This leopard lace long flowy tunic will bring all the vibes to your festival 'fit. Designed with a sleeveless bralette top with a leopard print, the long ruffled flyaway design is perf for pairing over denim shorts.
Fit & Features
- Sheer lace fabric
- Sleeveless bralette top, sweetheart neckline, lace trim, leopard print, underwire
- Adjustable spaghetti straps
- Open back, back strap with hook-eye closures, lower back cutout
- Long flyaway design, ruffled trim
- Flowy fit
- Runs true to size
Style Number/Barcode: 06003-000006
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Edgy Cat Eye Sunglasses
Add a touch of edgy to your look with these chic sunglasses. They feature a mini cat eye shape, lenses and a sleek metal frame.
Style Number/Barcode: 07008-0420
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Basic Essentials Midi Dress
Sometimes less is more! This basic midi length can be kept casual or paired with accessories to dress it up!
Fits & Features
- Tank Shoulder Straps
- Scoop Neckline
- Midi Length Silhouette
- Soft Knit Composition I Fully Lined
- Curve Hugging Fit I Ample Stretch
Black & Ivory: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-3587
Category Name: Vacation Looks
Price: $24.90
Availability: Out of Stock
Product Badge:- Clearance
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All About The Rhinestones Hoops
Make your look shine bright and sparkle with these glitzy hoops! They feature a large thin silver hued metal hoop with rhinestones adorned on half of the exterior and half on the interior. These glam hoops include omega closures.
Style Number/Barcode: 07001-4210
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Selfie Ring LED Light
#Nofilter Get your selfie game on point with glowing look! This portable selfie light easily clips on to phones and features a ring of LED powered lights. Selfie light features three levels of intensity to get the perfect lighting and an easy power button with different brightness levels. Includes a USB charger cable compatible with mini USB charging ports.
Style Number/Barcode: 07308-0391
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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Large Sleek Hoops
When your hoops are as big as your future. Keep it that way!
- Sleek design
- Omega closure
- Large design
- Available in gold + silver
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-3725
Category Name: Vacation Looks
Price: $2.97 $5.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ravishing Florals High-Slit Ruched Maxi Dress
Usher in romance in a maxi dress that features a sleeveless square neckline with spaghetti straps, an abstract floral pattern, ruching throughout to enhance curves, and a high side slit. Complete the look with block heels that will have you ready for your next brunch date!
Fit & Features
- Lined mesh fabrication
- Sleeveless square neckline
- Spaghetti straps
- Abstract floral pattern
- Ruching
- High side slit
- Maxi length hem
- Runs true to size
Style Number/Barcode: 05101-3859
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Style Polka Dot One-Shoulder Bikini Top
Shop Matching Bottoms: Flirty Style Polka Dot Twisted Bikini Bottoms
Fit & Features
- Polka-dot printed smooth nylon-blend fabric, plenty of stretch
- One-shoulder neckline, asymmetric thin tank strap
- Back hook and bar closure
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 07104-0713
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Style Polka Dot Twisted Bikini Bottoms
Shop Matching Top: Flirty Style Polka Dot One-Shoulder Bikini Top
Fit & Features
- Polka dot-printed smooth nylon-blend fabric, plenty of stretch
- Mid-rise waist
- Twisted side detail
- Cheeky bottom
- Form-hugging fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-0862
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Coastal Cutie Triangle Bikini Top
Shop Matching Bottoms: Coastal Cutie V-Cut Bikini Bottoms
Fit & Features
- Smooth double-lined nylon-blend fabric, plenty of stretch
- Triangle design, knotted detail at the bust
- Removable padding
- Adjustable spaghetti straps
- Back hook and bar closure
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 07104-0712
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny Dream Ruffled Off-The-Shoulder Bikini Top
With the sunny dream ruffled off-the-shoulder bikini top, you're ready to make waves. Featuring a ribbed knit, ruffled overlay, and sweetheart neckline, it's all about those carefree vibes.
Shop Matching Bottoms: Sunny Dream V-Cut Scrunched Bikini Bottoms
Fit & Features
- Ribbed knit fabric with smooth lining, plenty of stretch
- Elasticized off-the-shoulder sweetheart neckline
- Ruffled overlay, short sleeves
- Structured underwire, removable padding
- Back hook and bar closure
- Runs true to size
Style Number/Barcode: 07104-0711
Category Name: Vacation Looks
Price: $25.99
Availability: Out of Stock
Product Badge:- Ships Free
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Coastal Cutie V-Cut Bikini Bottoms
Shop Matching Top: Coastal Cutie Triangle Bikini Top
Fit & Features
- Smooth double-lined nylon-blend fabric, plenty of stretch
- Mid-rise waist, V-cut design
- Ruched side detailing
- Cheeky bottom
- Form-hugging fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-0861
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacay Mode Straw Clutch
Fit & Features
- Rectangular-shaped body
- Wooden top handle closure
- Braided straw material exterior
- Lined interior
Style Number/Barcode: 07203-2117
Category Name: Vacation Looks
Price: $12.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Retro Chic Contrast Trim Bikini Bottoms
Shop Matching Top: Retro Chic Contrast Trim Bikini Top
Fit & Features
- Smooth nylon-blend fabrication, plenty of stretch
- Contrast trim design
- Low-rise waist
- Cheeky bottom
- Form hugging-fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-0872
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Iconic Street Style Mid-Rise Cargo Denim Skort
Everyone will be eyeing you in this mid-rise denim skort on the street or at a concert! The faux wrap design adds a touch of urban flair, while the form-hugging fit flatters your figure.
Fit & Features
- Denim fabric
- Mid-rise waist, front button closure
- Faux wrap front
- Side cargo pocket
- Form-hugging fit, mini-length hem
- Runs true to size
Style Number/Barcode: 06603-0509
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free