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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Sleek Quilted Crossbody
Get a sleek and chic look with this stylish crossbody! It features a rectangular shape with a top zipper closure, a quilted diamond shaped design on the exterior, and an attached gold chain with a faux leather shoulder strap. Interior features two pockets.
Style Number/Barcode: 07203-0000
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wallet Crossbody With Metallic Hardware
Minimal with max impact. This black crossbody wallet features a flap opening with a zipper detail, a gold metallic hardware trim, and a detachable gold chain and faux leather shoulder strap for versatile wear. Wallet is composed of a faux leather material and includes several interior compartments and card slots.
Style Number/Barcode: 07201-0328
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Fresh Crossbody Wallet
We're loving this versatile, clean style! This crossbody wallet features a top zipper opening, a front pocket with a flap opening, multiple interior compartments and card slots, and a detachable shoulder strap. Wallet is composed of a taupe faux leather material.
Style Number/Barcode: 07201-0330
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Side Kick Wallet Wristlet
Keep this faithful companion at your side always! This black wallet features multiple card compartments, 2 zipper compartments, and an envelope design with a snap button closure. Wallet also includes a wrist strap and gold chain link shoulder strap. Composed of a faux leather material.
Style Number/Barcode: 07201-0327
Category Name: Vacation Looks
Price: $14.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Quilted Chain Wallet Crossbody
Keep your look on point with this elegant wallet cross body! It features a fold over design with snap button closure, multiple card slots, a pocket compartment with a snap button closure and a detachable leather strap. The body features a quilted design for an easily trendy look!
Style Number/Barcode: 07201-0324
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Forever Chic Convertible Wallet
This faux leather wallet has such a classic look it will forever be chic! It features a fold over design with a metal trim that opens up to multiple compartments on the inside. Bag features a faux leather wristlet as well as an included gold chain to easily convert into a cute crossbody!
Style Number/Barcode: 07201-0322
Category Name: Vacation Looks
Price: $10.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Brighten My Day Swimsuit
Brighten up the day with this neon pink one piece swimsuit! It features adjustable spaghetti straps that cross in the back, a plunging V neckline with a lattice lace up front with gold grommets, a high waist seam, and a high cut with partial coverage.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: 07109-0103
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glow Bright Cut Out Swimsuit
Glow hard this summer in this bright, neon green swimsuit! This one piece swim features a single shoulder strap with a triangle cut out, a large cutout at the waist, a moderate coverage bottom.Model is 5'7" with a 34" 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: 07109-0067
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Taking Chances Mesh Swimsuit
Make a bold plunge in this head turning one piece! The black swimsuit features a plunging V neckline with mini bar strap accents, unlined fitted mesh long sleeves, a high cut and a partial coverage bottom.Model is 5'7" with a 34" 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: 07109-0096
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stunner In Stripes Monokini
Showcase stunning looks in this red and white vertical striped monokini! It features small tank like shoulder straps, a scoop neckline, a low open back, and a partially covered bottom.RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Model is 5'6" with a 34" bust, 26.5" waist and 38" hips. Bra Size: 32D. She is wearing a size small.Style Number/Barcode: 07109-0092
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cut To The Chase Swimsuit
Cut out the drama and head straight for good vibes in this statement making black swimsuit! It features a one shoulder neckline with wide shoulder strap, an asymmetrical cut out and a cheeky bottom.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: 07109-0087
Category Name: Vacation Looks
Price: $16.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sporty Luxe Corduroy Baseball Cap
Fit & Features
- Corduroy material
- Wide brim
- Baseball cap design
- Adjustable back strap
Style Number/Barcode: 07302-1736
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Deep Plunge Caged Swimsuit
Take a plunge in the deep end with this sexy one piece bathing suit. It features a plunging V neckline, caged strap details, spaghetti halter straps that lead to a single back strap, and a full coverage bottom.Model is 5'7" with a 34" 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: 07109-0086
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Laced Up Beauty Swimsuit
Lace up and get ready to glow this season! This must have black swimsuit features a straight neckline, removable padded cups, removable adjustable straps, a lattice front with silver metal grommets, matching lattice back and a high cut with cheeky coverage.Model is 5'6" with a 34" bust, 26" waist and 38" hips. Bra Size: 34D. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0078
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Radiate In Rhinestones Monokini
Radiate beauty in this rhinestone adorned monokini! It features a halter tie neckline, a low back, cut outs with lattice detailing on the sides, and a partial coverage bottom. The black swimsuit has sparkling rhinestones all over that will really catch the sun's rays!RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Model is 5'6" with a 34" bust, 26" waist and 38" hips. Bra Size: 32D. She is wearing a size small.Style Number/Barcode: 07109-0085
Category Name: Vacation Looks
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lattice Days Plunging Swimsuit
Take the plunge in lattice as you make a splash in this sexy royal blue one piece! It features a plunging neckline, adjustable narrow straps, side lattice cut outs and a cheeky bottom.Model is 5'6" with a 34" bust, 26" waist and 38" hips. Bra Size: 34D. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0077
Category Name: Vacation Looks
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tiki Tropics Swimsuit
Hit the tropics in this vacay ready one piece! The black swimsuit features a plunging V neckline, adjustable narrow straps and a high cut with partial coverage bottom. The palm leaf print features green hues complemented with red hues. Swimsuit is composed of a lined mesh fabric that offers a form hugging fit with a moderate stretch. Be sure to pick up the matching cover up!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: 07109-0070
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ruched And Ready Swimsuit
Get ready to soak up the sun in this sexy one piece! Swimsuit features an olive green color, a plunging V neckline,padded cups, adjustable narrow straps and ruched sides with tie accents.RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Model is 5'6" with a 34" bust, 26.5" waist and 38" hips. Bra Size: 32D. She is wearing a size small.Style Number/Barcode: 07109-0074
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lace Up In Lattice Swimsuit
Lace up in this sexy black swimsuit to showcase curves! It features a scoop neckline, narrow shoulder straps, side lattice detailing and a high cut with cheeky coverage.
Model is 5'6" with a 34" bust, 26" waist and 38" hips. Bra Size: 34D. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07109-0075
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Under The Sun Monokini
Bask under the sun in this adorable printed monokini! It features a tank cut with a scoop neckline, shoulder straps with a cute knotted detail, a low back, and a high cut with a partial coverage bottom. The swimsuit showcases a tropical black and white palm tree print.RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Model is 5'6" with a 34" bust, 26" waist and 38" hips. Bra Size: 32D. She is wearing a size small.Style Number/Barcode: 07109-0072
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Untamed Ties Swimsuit
Let that wild side out this swim season in this fierce swimsuit! This one piece features a plunging neckline with a front tie detail, adjustable straps, a snap closure at the back, large front and back cut-outs in the mid section, and high rise bottoms with a cheeky fit.RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Model is 5'6" with a 34" bust, 26.5" waist and 38" hips. Bra Size: 32D. She is wearing a size small.Style Number/Barcode: 07109-0051
Category Name: Vacation Looks
Price: $14.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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By Your Side Lattice Swimsuit
This chic black one piece is all you need to make a splash this season! It features a plunging V neckline, narrow shoulder straps, lattice straps on the side and a high cut with partial coverage bottom.Model is 5'6" with a 34" bust, 26" waist and 38" hips. Bra Size: 34D. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0042
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Day Drunk One Piece Swimsuit
Sun's out, drinks up! This graphic black swimsuit says it all with a plunging neckline, thin shoulder straps, a plunging matching back and a high cut with partial coverage bottom. The graphic reads: "Day Drunk" in a contrasting white print.Model is 5'6" with a 34" bust, 26" waist and 38" hips. Bra Size: 34D. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0046
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fish Out Of Water Swimsuit
Fish this sexy piece out of the water! The one piece swimsuit has a scoop neck paired with wide straps and a basic, bikini bottom. The fishnet swimsuit is also complemented with an solid knit overlay that gives the illusion of a two piece, bikini top and bottom.RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0044
Category Name: Vacation Looks
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free