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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Just My Type Clear Cork Wedges
These wedges are just your type, girl! The wedges feature an open back with a clear PVC heel strap, an adjustable ankle strap, an open almond toe with a clear PVC strap, and a cork wedge heel. Complete look with a ruffled mini dress and a sheer duster.
Fit & Features
- Open back with clear PVC heel strap
- Adjustable faux leather ankle strap
- Open almond toe
- Clear PVC strap over the toe
- Cork wedge heel
Style Number/Barcode: 07406-0234
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Basic And Chic Two-Tone Sandals
These basic and chic faux leather sandals are a wardrobe must-have this season. They feature an open round toe, a wide strap and thin adjustable ankle strap with a two-tone design, and an open back. Pair these flat sandals with a basic bodysuit and high-rise denim shorts.
Fit & Features
- Open round toe
- Wide strap
- Thin adjustable ankle strap
- Two-tone design
- Open back
- PU material
- Runs true to size
Style Number/Barcode: 07404-0747
Category Name: Vacation Looks
Price: $12.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Textures Long Duster
Keep it trendy a duster that is perf for lounging in. The duster features a draped open front, long sleeves, and a flowy long length. The duster is composed of a waffle-knit fabric that offers a relaxed fit with slight stretch. Complete look with the matching tank top and shorts.
Shop Matching Tank Top: Trendy Textures Cropped Tank
Shop Matching Shorts: Trendy Textures High Waist Shorts
Fit & Features
- Draped open front
- Long sleeves
- Waffle knit fabric
- Relaxed fit
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0167
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Layered In Glam Triple-Layered Body Chain Jewelry Set
Layer up in glam with a body chain jewelry set that adds that chic touch to your look! The set features a triple-layered design that drapes around the body. It includes a short necklace with a rhinestone adorned bar charm and a longer necklace with a rhinestone adorned round charm. The body chain features a center V-shaped rhinestone embellishment and a draped design. Complete the look with a swimsuit.
Fit & Features
- Jewelry set, triple-layer design
- Rhinestone adorned bar charm necklace
- Rhinestone adorned round charm necklace
- Body chain with a V-shaped rhinestone accent
- Draped, wrap-around design
- Lobster clasp closures
Style Number/Barcode: 07002-0756
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Vibes Butterfly Printed Mini Dress
Showcase those sweet and flirty vibes in this trendy knit mini dress. It features spaghetti straps, a square neckline, ruching down the sides, ties at the hem, and a short, form-hugging silhouette. The lightweight ribbed knit fabric has an adorable colorful butterfly print, making it a perf dress for the spring season. Complete your look with a denim jacket and strappy sandals.
Fit & Features
- Spaghetti straps
- Square neckline
- Ruched detailing and ties at the hem
- Mini-length, curve-hugging fit
- Unlined ribbed knit fabric
- Plenty of stretch
- Colorful butterfly print
Style Number/Barcode: 05102-1705
Category Name: Vacation Looks
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Flowy Woven Maxi Dress
Create an effortless and pretty look with this flowy woven maxi dress! It features dual adjustable spaghetti straps that lead to a cross-back design, a sheer detailed lace bust with lined cups, a V neckline, and a floor-sweeping silhouette. Complete the outfit with hoop earrings and strappy sandals.
Fit & Features
- Dual adjustable spaghetti straps
- Cross-back design
- Sheer lace bust with lined cups
- V neckline
- Smocked back
- Flowy floor-length silhouette
- Woven fabric
- Runs true to size
Style Number/Barcode: 05101-0531
Category Name: Vacation Looks
Price: $21.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glamorous Diva Square Frame Sunglasses
Showcase your status as a glamorous fashion diva with these must-have sunglasses. They feature an oversized square-shaped design with open sides with metal details, a tortoise-shell-hued frame, and tinted lenses. Pair these sunnies with a trendy shoulder bag and heeled mules.
Fit & Features
- Oversized square-shaped design
- Open sides with metal details
- Tortoise-shell-hued frame
- Tinted lenses
Style Number/Barcode: 07008-0856
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Posh Criss Cross Block Heels
Keep it posh and stylish with platform heels that elevate your outfits. The heels feature an open back, adjustable ankle strap, an open almond toe, criss-cross straps over the toe, a wide platform, and a block heel. The heels are composed of a faux nubuck material. Complete look with a ruffled mini skirt and tie front top.
Fit & Features
- Open back
- Adjustable ankle strap
- Open almond toe
- Criss-cross straps over the toe
- Wide platform
- Block heel
- Faux nubuck material
Style Number/Barcode: 07401-2733
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Style Off-The-Shoulder Romper
Showcase a chic effortless style this season with this adorable romper. It features an off-the-shoulder neckline, short tiered sleeves, a cinched high waist, and flowy shorts. Complete the look with hoop earrings and strappy sandals.
Fit & Features
- Off-the-shoulder neckline
- Short tiered sleeves
- Cinched high waist
- Flowy shorts
- Gauze fabric
- Runs true to size
Style Number/Barcode: 06303-0110
Category Name: Vacation Looks
Price: $15.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Weekend Fun Flutter Sleeve Tie-Front Top
This adorable tie-front top was made for weekend fun, designed with short flutter sleeves and an ultra-cropped hem. Style with the matching mini skort for the cutest vibe.
Shop Matching Bottoms: Weekend Fun Ruffled Mini Skort
Fit & Features
- Cotton woven fabric with swiss dot pattern, no stretch, partial knit lining
- V-neckline, tie-front design
- Short flutter sleeves
- Ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06204-000011
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendsetting Diva Flat Top Sunglasses
Showcase your trendy style like the fashion diva you are with these fab sunglasses! They feature an oversized design with square-shaped lenses, a flat top, and a plastic frame. Complete your look with a chic crossbody purse.
Fit & Features
- Oversized design
- Square-shaped lenses
- Flat top
- Plastic frame
Style Number/Barcode: 07008-0859
Category Name: Vacation Looks
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wanderlust Beauty Smocked Tube Top
You're a total wanderlust beauty, and this boho-chic top is a must for you! The top features a bohemian-print, a sleeveless sweetheart neckline, a twist-front accent, and a cropped hem. The top is composed of a stretchy smocked knit fabric that offers a relaxed fit with a moderate stretch. Complete look with flared bohemian pants.
Shop Matching Flared Pants: Wanderlust Beauty Flared Pants
Fit & Features
- Sleeveless sweetheart neckline
- Twist-front accent
- Cropped hem
- Bohemian print
- Smocked knit fabric
- Relaxed fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3194
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Laidback Vibes Maxi Skirt
Showcase a cool, laidback style in this breezy maxi skirt! It features a high-rise waist with a tie-front detail, a flowy floor-length silhouette, and a stylish front slit. Complete your look with a crochet bralette and strappy sandals.
Fit & Features
- High-rise waist, elastic banded back
- Tie-front
- Flowy silhouette
- Front slit
- Lightweight gauze fabric, no stretch
- Runs true to size
Style Number/Barcode: 06301-0088
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Essential Chic Surplice Gauze Jumpsuit
Stun in a chic jumpsuit that is perf for keeping it casually cute! The jumpsuit features a plunging sleeveless V-neckline, halter neck ties, and an elastic waistband. The relaxed fit bodice leads to a straight leg accented with slant pockets. The jumpsuit is composed of a gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with mules.
Fit & Features
- Sleeveless V-neckline
- Halter neck ties
- Elastic waistband
- Slant pockets
- Straight leg
- Gauze knit fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06302-0187
Category Name: Vacation Looks
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Chiffon High-Low Duster
Bring the charm with a chic duster that is the perf lightweight layer for spring! It features short flutter sleeves, a V neckline, a front button closure, and a flowy high-low hem. The sheer chiffon fabric has no stretch. Wear this airy duster over your swimsuit as a pretty cover-up.
Fit & Features
- Short flutter sleeves
- V neckline
- Front button closure
- High-low hem
- Flowy fit
- Sheer chiffon fabric with no stretch
- Runs true to size
Style Number/Barcode: 06204-0662
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Boho Tassel Straw Clutch
Fun and flirty! This dome-shaped clutch has a straw exterior and multi-colored tassel details with a zipper closure. Complete look with a ribbed mini dress and sunnies.
Fit & Features
- Dome-shaped
- Straw exterior
- Multi-colored tassel detail
- Zipper closure
Style Number/Barcode: 07203-0555
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Vibes Straw Tote
Go for those summer vibes with this adorable basic straw tote! It features an open-top design and round handles. Complete your look with cute wedges and a trendy Panama hat.
Fit & Features
- Open-top design
- Round handles
- Straw material
Style Number/Barcode: 07203-0569
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sun's Out Straw Tote
Style up your outfits with this adorable straw tote for the warmer months! It features an open-top, round handles, multiple pom accents, and a straw exterior. Complete your look with chic sunglasses and strappy sandals.
Fit & Features
- Open-top
- Round handles
- Pom accents
- Straw material
Style Number/Barcode: 07203-0571
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless And Breezy Chiffon Kimono
Layer on this breezy chiffon kimono for an effortlessly stylish look! It features short sleeves, an open front, a tassel trim, and a flowy, relaxed fit. Pair this kimono over your fave swimsuit to lounge poolside.
Fit & Features
- Short sleeves
- Open front
- Tassel trim
- Flowy, relaxed silhouette
- Sheer chiffon fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-0830
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Good Vibes Ribbed One Piece Swimsuit
Bring those good vibes this season with a swimsuit that is perfect for working on that summer glow! The swimsuit features a plunging V-neckline, a zippered front with a mini O-Ring accent, adjustable shoulder straps, and a plunging open back. Complete look with sunnies and sandals.
Fit & Features
- Plunging V-neckline
- Zippered front with O-Ring accent
- Adjustable shoulder straps
- Plunging open back
- Cheeky bottom
- Ribbed
- Form hugging fit runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0236
Category Name: Vacation Looks
Price: $4.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Star Of The Show Rhinestone Drop Earrings
You'll be the star of the show in these dazzling drop earrings! They feature a round post and a drop design with a dainty chain-link and a rhinestone adorned star accent. Complete the look with a statement ring and a trendy anklet.
Fit & Features
- Round post
- Drop design
- Chain-link
- Rhinestone adorned star detail
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0745
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Aubrielle Formal Floral Chiffon A-Line Dress
Special Occasion
Create a head-turning moment with a formal dress that brings the luxe to your evening. Aubrielle features a plunging V-neckline with a pleated bodice, thin adjustable cross-straps, a floral print, and a sweeping A-line silhouette. The dress is composed of a semi-sheer chiffon fabric that offers a relaxed fit. Complete your look with heels and a sleek envelope clutch.
Fit & Features
- Sleeveless V-neckline
- Pleated bodice
- Thin adjustable cross-straps
- Back zipper and hook and eye closure
- Floral print
- A-line silhouette, relaxed fit
- Semi-sheer chiffon fabric, mini skirt length lining
- Runs true to size
Style Number/Barcode: 05002-0697
Category Name: Vacation Looks
Price: $29.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Free Spirit Knit Skater Dress
Live your best in this season ready skater dress!
Fit & Features
- Plunging V-Neckline
- Halter Neck Tie Straps
- Skater Silhouette
- Fully Lined Gauze-Like Fabric
- Relaxed Fit
- Minimal Stretch
Style Number/Barcode: 05102-0485
Category Name: Vacation Looks
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Frill Seeker Ruffled Denim Shorts
These denim shorts? Total heartthrob. With a mid-rise waist and ruffled hem, it’s giving playful, pretty, and just the right amount of sass for any OOTD.
Fit & Features
- Cotton denim fabric, no stretch
- Mid-rise waist
- Side zipper and hook-eye closure
- Ruffled trim hem
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 06303-000015
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free