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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Strut It Out Faux Leather Booties
Strut it out in chic booties that give you that extra pep of confidence! The booties feature an around the ankle fit, an inner zipper closure, a pointed toe, and composed of a faux leather material. Complete look with a faux suede mini skirt and crop top.
Fit & Features
- Around the ankle fit
- Inner zipper closure
- Pointed toe
- Faux leather material
Style Number/Barcode: 07403-1236
Category Name: Vacation Looks
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Intentions Cutout Denim Romper
Keep your look on point with a stylish romper that is perf to dress up for that upcoming BBQ or weekend getaway! The romper features a sweetheart neckline, lace-up front short sleeves with a ruffled hem, a sexy waist cutout, and wide-leg shorts. Complete look with wedges and sleek hoops.
Fit & Features
- Sweetheart neckline, lace-up front, adjustable drawstring
- Short sleeves with ruffled trim
- Waist cutout
- Back zipper, hook and eye closure
- Wide-leg shorts
- Denim fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06603-0224
Category Name: Vacation Looks
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Denim Diva Espadrille Wedges
Showcase your love for denim with wedges that channel those casual vibes just right! The wedges feature an open almond toe, a denim strap over the toe, a closed back with an adjustable strap, and an espadrille wedge. Complete look with a floral mini dress for a spring-ready outfit.
Fit & Features
- Closed-back
- Adjustable ankle strap
- Open almond toe
- Denim strap over the toe
- Espadrille wedge
Style Number/Barcode: 07406-0243
Category Name: Vacation Looks
Price: $12.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Fashion Diva Sunglasses
Yes babe, showcase the major fashion diva you are in these chic sunglasses! They feature an oversized square-shaped design with a plastic frame, open side detailing, and gold metal trim accents. Pair these fabulous shades with a casual dress and heeled mules.
Fit & Features
- Oversized square-shaped design
- Tinted lenses
- Plastic frame and arms
- Open side detailing
- Gold metal trim accents
Style Number/Barcode: 07008-0822
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Level Up Ruched Knit Midi Dress
Level up your basic look with this trendy ruched knit midi dress. It features a sleeveless bodice, bungee spaghetti straps, a square neckline, all-over ruched detailing, and a mid-length, curve-hugging silhouette. The soft brushed knit fabric includes a lining and offers plenty of stretch for comfortable wear. Complete your outfit with a layered necklace and sleek heels.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Strapless bra recommended
- All-over ruched detailing
- Mid-length, form-fitting style
- Lined-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4437
Category Name: Vacation Looks
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fab Florals Tie Front Top
Keep it fab in a floral top that brings the charm! The top features a floral print, long sleeves with an elastic cuff, a tie front bodice with a cropped hem. The top is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete your look with high waist jeans.
Fit & Features
- Floral print
- Long sleeves with elastic cuff
- Tie front bodice
- Cropped hem
- Lightweight woven fabric
- Relaxed fit
- Minimal stretch
Style Number/Barcode: 06204-0646
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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In the Clear Faux Patent Leather Wedges
Clearly stay on-trend with wedges that elevate. The wedges feature a faux patent leather footbed and wedge, a peep toe, and a clear PVC strap. Complete your look with a floral print mini dress.
Fit & Features
- Almond toe
- Wedge heel
- Peep toe
- Clear PVC strap
- Faux patent leather footbed
- Runs true to size
Style Number/Barcode: 07406-0244
Category Name: Vacation Looks
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Neon Drama Snake Print Swim Top
Bring the drama in this bold neon snake print swim top, a perf option for weekend beach trips. It features adjustable spaghetti straps, a scoop neckline, a sultry front slit, and a banded front hem. Pair this swim top with the matching swim bottoms and some chic sunglasses.
Shop Matching Swim Bottoms: Neon Drama Snake Print Swim Bottoms
Fit & Features
- Adjustable spaghetti straps
- Scoop neckline
- Front slit
- Banded front hem
- Snake print
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0485
Category Name: Vacation Looks
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Neon Drama Snake Print Swim Bottoms
Bring the drama in these bold neon snake print swim bottoms, a perf option for weekend beach trips. They feature a high-cut cheeky fit with thin side straps. Pair these swim bottoms with the matching swim top and some chic sunglasses.
Shop Matching Swim Top: Neon Drama Snake Print Swim Top
Fit & Features
- High-cut cheeky fit
- Thin side straps
- Snake print
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0633
Category Name: Vacation Looks
Price: $5.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Basic Chic Tank Swim Top
Keep your beach-ready look basic yet still chic in this must-have swim top. It features a tank-like design with thin straps that lead to adjustable spaghetti straps, a scoop neckline, and a sexy front slit detail with an elastic banded hem. Pair this swim top with the matching swim bottoms and some trendy sunglasses.
Shop Matching Black Swim Bottoms: Basic Chic Banded Swim Bottoms
Shop Matching Olive Swim Bottoms: Basic Chic Side Tie Swim Bottoms
Fit & Features
- Tank-like design
- Thin straps that lead to adjustable spaghetti straps
- Scoop neckline
- Front slit
- Elastic banded hem
- No padding
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0506
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Flirt Floral Mini Tube Dress
Bring the sweet flirty vibes to your weekend plans in this cute mini tube dress with a dainty floral print on lined chiffon fabric. The strapless smocked bodice leads to a V-shaped waist, tiered ruffled design, and flowy skater silhouette.
Fit & Features
- Woven chiffon fabric with stretchy knit lining, dainty floral print
- Strapless straight-across neckline
- Stretchy smocked bodice
- V-shaped waist
- Tiered ruffled design
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05101-4077
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Basic Chic Side Tie Swim Bottoms
Keep your beach-ready look basic yet still chic in these must-have swim bottoms. They feature a high-cut, cheeky fit with side tie closures. Pair these swim bottoms with the matching swim top and some trendy sunglasses.
Shop Matching Swim Top: Basic Chic Tank Swim Top
Fit & Features
- High-cut, cheeky fit
- Side tie closures
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0656
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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A Perfect Pick Slide-On Flats
These chic slide-on flats are the perfect pick to pair with your everyday 'fits! They feature a slightly square toe with a croc-embossed wide strap and a flat sole. Style these flats with boyfriend jeans and a cute crop top.
Fit & Features
- Slide-on design
- Slightly square toe
- Croc-embossed wide strap
- Flat sole
- PU material
Style Number/Barcode: 07404-0707
Category Name: Vacation Looks
Price: $12.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Elise Frayed Denim Mini Skirt
A denim skirt is the one staple piece that is always in style! Add the stylish Elise denim mini skirt to your collection and dress with a floral blouse to create a casual brunch outfit. The skirt features a high rise waist, a single-button and zipper closure, a traditional five-pocket design, and a frayed hem. The skirt is composed of a light-medium wash denim fabric that offers a form-hugging fit and has no stretch.
Fit & Features
- High rise waist
- Single-button and zipper closure
- Traditional five-pocket with belt loop design
- Frayed hem
- Light-medium wash denim fabric
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06601-0037
Category Name: Vacation Looks
Price: $13.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Basic Chic Banded Swim Bottoms
Keep your beach-ready look basic yet still chic in these must-have swim bottoms. They feature a high rise elastic banded waist and a high-cut, semi-cheeky fit. Pair these swim bottoms with the matching swim top and some trendy sunglasses.
Shop Matching Swim Top: Basic Chic Tank Swim Top
Fit & Features
- High rise elastic banded waist
- High-cut, semi-cheeky fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0655
Category Name: Vacation Looks
Price: $8.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Babe Burnout Babydoll Top
Showcase your sweet and flirty side with a cute babydoll-styled top! The top features a sleeveless sweetheart neckline, a single hook and eye fasten closure, adjustable spaghetti straps, and a velvet burnout floral design. The top is composed of a sheer mesh fabric that offers a form hugging fit with minimal stretch. Complete look with a bralette and a high waist skirt.
Fit & Features
- Sleeveless sweetheart neckline
- Velvet burnout floral design
- Hook and eye fasten closure
- Adjustable spaghetti straps
- Sheer mesh fabric
- Relaxed fit
- Minimal stretch
Style Number/Barcode: 06003-1219
Category Name: Vacation Looks
Price: $6.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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High Tide Ruffled Bikini Top
Create a stylish beachside look with this sexy bikini top. The bikini top features a sleeveless straight neckline with a ruffled trim, a square-shaped cutout at the bust, and double-row tie back straps for a secure fit. Complete your look with the matching bikini bottoms and sunglasses.
Shop Matching Bikini Bottoms: High Tide High Rise Bikini Bottoms
Fit & Features
- Sleeveless straight neckline
- Ruffled trim
- Square-shaped cutout
- Double-row tie back straps
- Matching bikini bottoms sold separately
Style Number/Barcode: 07104-0504
Category Name: Vacation Looks
Price: $5.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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High Tide High Rise Bikini Bottoms
Create a stylish beachside look with these sexy bikini bottoms. The bottoms feature a high cut style with a high rise waist, side ties, and a cheeky fit. Complete your look with the matching bikini top and sunglasses.
Shop Matching Bikini Top: High Tide Ruffled Bikini Top
Fit & Features
- High cut
- High rise waist
- Side ties
- Cheeky fit
- Matching bikini top sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0652
Category Name: Vacation Looks
Price: $4.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Sheer Mesh Swim Bottoms
Showcase those sultry-chic vibes in these stunning swim bottoms! They feature a high waist with two sexy sheer mesh inserts and a semi-cheeky fit. Pair these swim bottoms with the matching swim top and a flowy duster.
Shop Matching Swim Top: Sultry Sheer Mesh Swim Top
Fit & Features
- High waist
- Two sheer mesh inserts
- Semi-cheeky fit
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0650
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sultry Sheer Mesh Swim Top
Showcase those sultry-chic vibes in this stunning swim top! It features a one-shoulder neckline with a tank strap and sexy sheer mesh inserts. Pair this swim top with the matching swim bottoms and a flowy duster.
Shop Matching Swim Bottoms: Sultry Sheer Mesh Swim Bottoms
Fit & Features
- One-shoulder neckline
- Tank strap
- Sheer mesh inserts
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0502
Category Name: Vacation Looks
Price: $9.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweetly Chic Tie Front Crop Top
Make a sweet impression with this chic crop top! The top is perf for your next date night! The top features a gorge floral print, a trendy sweetheart neckline, a double row of tie-front accents, a sexy cutout with bar strap accent, long sleeves, and a smocked back. The top is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with skinny jeans and mules.
Fit & Features
- Floral print, sweetheart neckline
- Double-row tie fronts
- Midriff cutout, cropped hem
- Bar strap with buttons
- Long sleeves with elastic cuff
- Smocked back
- Semi-sheer lightweight woven fabric, minimal stretch
Style Number/Barcode: 06003-1237
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Boldly Chic Tie Front Crop Top
Make a bold impression with this chic crop top! The top is perf for your next date night! The top features a trendy sweetheart neckline, a double row of tie-front accents, a sexy cutout with bar strap accent, long sleeves, and a smocked back. The top is composed of a semi-sheer lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with skinny jeans and mules.
Fit & Features
- Sweetheart neckline
- Double-row tie fronts
- Midriff cutout, cropped hem
- Bar strap with buttons
- Long sleeves with elastic cuff
- Smocked back
- Semi-sheer lightweight woven fabric, minimal stretch
Style Number/Barcode: 06003-1236
Category Name: Vacation Looks
Price: $4.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Classic Style Aviators
Rock a classic vibe with sunglasses that are always in style! The sunglasses feature a sleek metal frame, an aviator design, and sleek metal arms. Complete the look with a floral maxi dress and wedges for a brunch-ready outfit.
Fit & Features
- Sleek metal frame
- Nose pads
- Aviator design
- Metal arms
Style Number/Barcode: 07008-0809
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Layers Dainty Cross Charm Necklace Pack
Layer on the style with a necklace set that keeps you on-trend! The necklace pack includes two necklaces. One necklace features a snake chain design and the other necklace features a dainty layered design. The layered necklace features a cross charm and bar charm. Both necklaces include a lobster clasp closure. Complete look with a ruffled floral dress.
Fit & Features
- Pack includes two necklaces
- Snake chain
- Layered necklace
- Cross charm
- Bar charm
- Lobster clasp closure
Style Number/Barcode: 07002-0675
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale