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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Smocked Tie-Front Tube Top
Give your look a fab twist with a cute tube top to pair with your favorite high waist bottoms. The tube top features a strapless sweetheart neckline, a twist-front accent, a cropped hem, and is composed of a smocked knit fabric. Complete the look with a denim skirt and wedges.
Fit & Features
- Strapless sweetheart neckline
- Tie-front accent
- Cropped hem
- Smocked knit fabric
- Form-hugging fit
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-3163
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lace-Up Sleek PVC Sandals
Lace-up in cute sandals that keep your look sleek and stylish. The sandals feature lace-up straps, a closed back, an open square toe, and a clear PVC strap over the toe. The sandals are composed of a faux leather material. Complete look with a floral romper.
Fit & Features
- Lace-up straps
- Open square toe
- Clear PVC strap over the toe
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-0739
Category Name: Vacation Looks
Price: $12.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Vibes Mesh Headwrap
Channel those chic vibes with a headwrap that keeps tresses relaxed and stylish. The headwrap is composed of mesh fabric and has an oversized-fit wrap-around design. Complete your look with the matching swim coverup and a cute two-piece swimsuit for a fab day out!
Shop Matching Swim Coverup: Cinched and Chic Mesh Swim Coverup
Fit & Features
- Wrap-around design
- Mesh material
Style Number/Barcode: 07305-0276
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Iconic Style High-Rise Cut-Off Denim Shorts
These iconic denim shorts will forever be a flattering staple in your closet! The high-rise waist provides a flattering and comfortable fit, while the frayed hem adds a touch of edginess.
Fit & Features
- Medium wash denim, non-stretch
- High-rise waist
- Frayed hem
- Front five-button fly closures
- Five-pocket styling, belt loop accents
- Runs true to size
Style Number/Barcode: 06603-000001
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Cutie Linen Skater Dress
Get a casual cute look in this lightweight linen skater dress. It features adjustable spaghetti straps, a lined crochet bodice with a V neckline, an open back with a tie closure, and a flowy, skater silhouette. The gauze and linen fabric has a knit lining. Complete your outfit with adorable wedges and a chic shoulder bag.
Fit & Features
- Adjustable spaghetti straps
- Lined crochet bodice with a V neckline
- Open back with a tie closure
- Short skater silhouette
- Gauze and linen fabric with no stretch
- Knit lining
- Runs true to size
Style Number/Barcode: 05102-0233
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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The Classic Tie Back Bikini Top
Classic tie-back bikini tops are always in style! Fall back on this bikini top that features triangle cups, neck-ties, and tie-back straps for a secure fit. Complete look with the matching bikini bottoms, matching dress, and sunnies.
Shop Matching Bikini Bottoms: The Classic Low Rise Bikini Bottoms
Shop Matching Coverup: Drawn To You Mesh Cover Up
Fit & Features
- Triangle cups
- Removable padding
- Sleek neck ties
- Tie-back straps
- Form hugging fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0544
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Drawn To You Mesh Cover Up
Get drawn in with this chic coverup that brings sheer appeal! The coverup features a crew neckline, a ruched drawstring at the side, and a mini-length silhouette. The coverup is composed of a sheer unlined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with the matching bikini set, sunnies, and sandals!
Shop Matching Bikini Top: The Classic Tie Back Bikini Top
Shop Matching Bikini Bottoms: The Classic Low Rise Bikini Bottoms
Fit & Features
- Crew neck
- Sleeveless
- Ruched drawstring at the side
- Mini length silhouette
- Unlined mesh fabric
- Form hugging fit
Style Number/Barcode: 06001-3135
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cinched and Chic Mesh Swim Coverup
Keep it chic under the cabana in a cinched skirt coverup! The skirt features a high-rise waist, a cinched side seam, and an asymmetrical hem. The skirt coverup is composed of a sheer unlined mesh fabric that offers a form-hugging fit. Complete your look with the matching headwrap, a cute two-piece swimsuit, and sunnies.
Shop Matching Headwrap: Chic Vibes Mesh Headwrap
Fit & Features
- High-rise waist
- Ruched side drawstring
- Asymmetrical hem
- Mini-length silhouette
- Sheer unlined mesh fabric
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06501-0374
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Crochet Beauty Lattice Back Top
You'll look like a total boho beauty in this trendy crochet top. It features short cap sleeves, a scoop neckline, a lattice back design with a tie detail, and a form-hugging fit. The sheer crochet fabric has no stretch. Pair an adorable bralette under this top and style with denim shorts.
Fit & Features
- Short cap sleeves
- Scoop neckline
- Lattice back design
- Tie closure with tassel details
- Form-fitting style
- Sheer crochet fabric with no stretch
- Runs true to size
Style Number/Barcode: 06005-0883
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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You're The Zest Lemon Print Bikini Bottoms
These bikini bottoms will have you looking your best this season with a too-cute lemon print! The bikini bottoms feature a mid-rise waist, a lemon print, and a cheeky bottom. Complete look with the matching bikini top and sunnies.
Shop Matching Bikini Top: You're The Zest Lemon Print Bikini Top
Fit & Features
- Mid-rise waist
- Lemon print
- Cheeky bottom
- Form hugging fit
- Moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0645
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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You're The Zest Lemon Print Bikini Top
This bikini top will have you looking your best this season with a too-cute lemon print! The bikini top features a sleeveless scoop neckline, a smocked bodice, a lemon print, removable padding, and adjustable spaghetti straps. Complete look with the matching bikini bottoms and a pair of stylish sunnies.
Shop Matching Bikini Bottoms: You're The Zest Lemon Print Bikini Bottoms
Fit & Features
- Sleeveless scoop neckline
- Lemon print
- Smocked bodice
- Removable padding
- Adjustable spaghetti straps
- Form hugging fit, moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0497
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All The Drama Cutout One Piece Swimsuit
Let this one-piece swimsuit make a dramatic splash for your beachside look! The sexy one-piece swimsuit features a sleeveless square neckline with spaghetti straps, a sexy cutout at the midriff, an asymmetrical strap, and a high cut bottom with a thong bottom. Complete look with sunnies.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Cutout
- Asymmetrical strap
- High cut bottom
- Thong bottom
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 07109-0246
Category Name: Vacation Looks
Price: $4.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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East Coast Graphic Tee
Rep the east coast in style with this trendy graphic tee! It features a crew neckline, short sleeves, a mid-length, form-hugging fit, and a center graphic that reads "East Coast." Complete your look with biker shorts and cute sneaks.
Fit & Features
- Crew neckline
- Short sleeves
- Mid-length hem
- Center graphic that reads "East Coast"
- Jersey knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-0758
Category Name: Vacation Looks
Price: $5.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On-Trend Destructed Denim Mini Skirt
Keep your everyday style on-trend for spring in this adorable denim mini skirt! It features a high-rise waist, a traditional five-pocket and belt loop design, a front button and hidden zipper closure, distressed details, a short raw cut hem, and a form-hugging silhouette. Pair this skirt with a floral crop top and strappy sandals.
Fit & Features
- High-rise waist
- Traditional five-pocket and belt loop design
- Front button and hidden zipper closure
- Destructed details and a raw cut hem
- Mini-length, form-hugging fit
- Light wash denim fabric with minimal stretch
- Runs true to size
Style Number/Barcode: 06601-0038
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wrap Me In Glam Mesh Maxi Skirt
Wrap yourself in a chic mesh coverup skirt that makes a sheer impression. The skirt features an elastic high-rise waist, a high side slit, and a maxi-length silhouette. The skirt is composed of a sheer unlined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with the matching crop top and sunnies.
Shop Matching Crop Top: Wrap Me In Glam Mesh Maxi Skirt
Fit & Features
- Elastic high-rise waist
- High side slit
- Maxi-length silhouette
- Unlined mesh fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0260
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sunkissed Beauty One-Piece Swimsuit
You'll look like a sunkissed beauty in this stunning one-piece swimsuit! It features halter straps, a low scoop neckline, a backless design with tie-back straps, side cutouts at the waist with a criss-cross design, and a semi-cheeky fit. The all-over tropical floral print is perf for the warmer weather. Complete your look with strappy sandals.
Fit & Features
- Halter straps
- Low scoop neckline
- Backless design
- Tie-back straps
- Side cutouts with a criss-cross design
- Semi-cheeky fit
- Tropical floral print
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0242
Category Name: Vacation Looks
Price: $5.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fierce And Flirty Swim Top
Bring a fierce and flirty vibe to your poolside look with this on-trend swim top! It features a one-shoulder neckline, a center cutout above the bust, and a cutout at the hem that goes from the front to the back. Pair this swim top with the matching swim bottoms and some chic sunglasses.
Shop Matching Bottoms: Fierce And Flirty Swim Bottoms
Fit & Features
- One-shoulder neckline
- Center cutout above the bust
- Cutout at the hem
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0530
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Brunch At Noon Off-The-Shoulder Floral Romper
Step out for brunch in this floral off-the-shoulder romper with a flirty tie-waist and ruffled hem for a playful look.
Fit & Features
- Floral print, chiffon fabric, woven shorts lining
- Off-the-shoulder neckline, ruffled short-sleeve cuffs
- Back zipper and hook-eye closure
- Tie-waist
- Flowy ruffled short hem
- Runs true to size
Style Number/Barcode: 06403-1093
Category Name: Vacation Looks
Price: $20.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Headturner Cutout Mesh One Piece Swimsuit
Cause a head-turning moment with a swimsuit that is boldly fab! The one-piece swimsuit features a plunging sweetheart neckline, sleek spaghetti straps, a caged detail, sexy cutouts at the midriff and waist, a sheer mesh panel, and a cheeky bottom. Complete look with jelly sandals and sunnies.
Fit & Features
- Sleeveless sweetheart neckline, spaghetti straps
- Caged design
- Removable padded cups
- Cutouts at the midriff and waist
- Mesh panel
- Double row of slide hook closures
- High cut with a cheeky bottom
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0256
Category Name: Vacation Looks
Price: $5.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Get Sprung Floral Bikini Bottoms
Get spring on these cute bikini bottoms! The bottoms feature a high-rise waist, a floral print, a cute tie-waist belt, and a cheeky bottom. Complete the look with the matching bikini top and sandals.
Shop Matching Bikini Top: Get Sprung Floral Bikini Top
Fit & Features
- High rise waist
- Floral print
- Tie-waist belt
- Cheeky fit
- Form hugging fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0674
Category Name: Vacation Looks
Price: $4.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Get Sprung Floral Bikini Top
Get sprung on this cute bikini top! The top features a plunging sweetheart neckline, molded cups, a floral print, adjustable spaghetti straps, and a slide-hook closure. Complete the look with the matching bikini bottoms and jelly sandals.
Shop Matching Bikini Bottoms: Get Sprung Floral Bikini Bottoms
Fit & Features
- Sleeveless sweetheart neckline
- Molded cups
- Adjustable spaghetti straps
- Floral print
- Slide-hook closure
- Form hugging fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0526
Category Name: Vacation Looks
Price: $9.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pretty Palm Paradise Bikini Top
Keep it pretty underneath the palm trees with bikini bottoms that take you to paradise. The bikini top features an off-the-shoulder neckline, a sweetheart bust, off-the-shoulder straps, and a palm tree print. Complete your look with the matching bikini bottoms and jelly sandals.
Shop Matching Bikini Bottoms: Pretty Palm Paradise Bikini Bottoms
Fit & Features
- Off the shoulder neckline
- Sweetheart bust
- Palm tree print
- Form hugging fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0525
Category Name: Vacation Looks
Price: $9.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pretty Palm Paradise Bikini Bottoms
Keep it pretty underneath the palm trees with a bikini top that takes you to paradise. The bikini bottoms feature a low-rise hipster, a palm tree print, bar strap cutouts at the waist, and a cheeky fit. Complete your look with the matching bikini top and jelly sandals.
Shop Matching Bikini Top: Pretty Palm Paradise Bikini Top
Fit & Features
- Low-rise waist
- Palm tree print
- Bar strap cutouts at the waist
- Cheeky fit
- Form hugging fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0673
Category Name: Vacation Looks
Price: $1.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Babygirl Rhinestone Baseball Cap
Dazzle on baby girl with a cap that is part sporty, part glam. The cap features a traditional baseball cap design and a rhinestone embellished scrip that reads "Babygirl".
Complete the look with a crop top and cutoff jeans.Fit & Features
- Baseball cap design
- Rhinestones
- Script that reads "Babygirl"
Style Number/Barcode: 07302-0293
Category Name: Vacation Looks
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale