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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Botanical Beauty Off Shoulder Tunic
Get into that out-of-office mood with this flowy tunic! It's never too early to start planning that getaway trip

Fits & Features
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Off Shoulder Design
- Quarter Length Sleeves I Ruffle Cuffs
- Mini Length Silhouette I Ruffle Hem
- Woven Fabric I Lined Skirt
- Smocking At The Neckline, Cuffs & Midsection
- Form Hugging I Plenty Of Stretch
Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06001-2472
Category Name: Vacation Looks
Price: $14.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Off Shoulder Design
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Sweet Thing Ruffle Smocked Crop Top
Compliment your sweet side when you style in a femme romantic smocked crop top!
Fit & Features
- Square neckline
- Lace up center detail
- Smocked bodice
- Long chiffon sheer sleeves
- Ruffled wrist | Ruffled hemline
- Moderate stretch at smocked areas
Style Number/Barcode: 06003-0767
Category Name: Vacation Looks
Price: $11.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Chiffon Tie Front Duster
Chic and flowy, this tie front duster can easily be layered over your 'fits to make them all the more stylish.
Fit & Features
- Long loose sleeves | Elastic banded cuffs
- Tie front belt
- Flowy fit
- Sheer chiffon fabric | No stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06204-0363
Category Name: Vacation Looks
Price: $16.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Met Your Match Smocked Mini Skirt
Girl, we are SWOONIN' over your outfit! Charm them all in this look that's as sweet as you!
Shop Matching Top: Met Your Match Smocked Crop Top
Fits & Features
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High Rise, Elastic Waistband
- Smocking Throughout
- Ruffle Mini Length Hem
- Woven Fabric
- Curve Hugging Fit I Ample Stretch
- Matching Top Sold Separately
Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06401-0211
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Rise, Elastic Waistband
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Met Your Match Smocked Crop Top
Girl, we are SWOONIN' over your outfit! Charm them all in this look that's as sweet as you!
Shop Matching Skirt: Met Your Match Smocked Mini Skirt
Fits & Features
- Smocked Bodice
- Lettuce Trim Square Neckline & Cropped Hem
- Adjustable Drawstring At Center Front
- Roomy Long Sleeves
- Elastic, Ruffle Cuffs
- Matching Skirt Sold Separately
Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06003-0768
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fancy Fashionista Sunglasses
You're a major fancy fashionista, and need some shades to match your style! These sunglasses will amp up any 'fit.
- Cat eye shaped lenses
- Plastic frame
- Metal top rim
- Dark tinted lenses
- 100% UV Protection
Style Number/Barcode: 07008-0700
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Cat eye shaped lenses
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Money To Blow Rectangle Sunglasses
Look expensive in a pair of shades, like u got money to blow, and places 2 be

- Wrap around lenses
- Transparent frame
- Rectangular design
- Skinny
Style Number/Barcode: 07008-0702
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Live It Up Sunglasses
Live it up and glam up your look with these flashy sunnies!
- Large square shaped lenses
- Metal open sides
- Dark tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-0697
Category Name: Vacation Looks
Price: $5.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beach Bum Bikini Swim Top
Lay out and indulge in the beach bum vibe this summer! What better way to soak up the sun than in a sexy bikini? Don't forget to pick up the matching bottoms to complete the look!
Shop Matching Bottoms: Beach Bum Bikini Swim Bottoms
Fit & Features
- Triangle design
- Tie-string closures
- Fully lined
- Removable padding
- Moderate stretch | Sheen finish
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0319
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beach Bum Bikini Swim Bottoms
Lay out and indulge in the beach bum vibe this summer! What better way to soak up the sun than in a sexy bikini? Don't forget to pick up the matching top to complete the look!
Shop Matching Top: Beach Bum Bikini Swim Top
Fit & Features
- Mid-rise fit
- Tie-string hip
- Fully lined
- Moderate stretch | Sheen finish
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0475
Category Name: Vacation Looks
Price: $10.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Snake It Out Bikini Swim Top
Get sassy in snake print this summer bae! The neutral tones compliment that tan, and give u a fierce finish! Don't forget to pick up the matching bottoms!
Shop Matching Bottoms: Snake It Out Bikini Swim Bottoms
Fit & Features
- Triangle design
- Halter tie closure + back tie closure
- Removable padding
- Fully lined
- Snake print pattern
- Moderate stretch
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0310
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Snake It Out Bikini Swim Bottoms
Get sassy in snake print this summer bae! The neutral tones compliment that tan, and give u a fierce finish! Don't forget to pick up the matching bottoms!
Shop Matching Top: Snake It Out Bikini Swim Top
Fit & Features
- Triangle design
- String hips
- Cheeky bottom
- Fully lined
- Snake print pattern
- Moderate stretch
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07105-0466
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold Vibe Floral Print Strapless Bodycon Mini Dress
Look gorgeous at your getaway and show off a bold vibe in this knit mini dress designed with a large floral print to turn heads. It features a strapless straight-across neckline and a short bodycon silhouette to hug your curves.
Fit & Features
- Smooth knit fabric with knit lining, plenty of stretch
- Large floral print
- Strapless straight neckline, no-slip strip
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-6047
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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High Rise Distressed Cut Off Jean Shorts
Everyone needs a classic pair of vintage looking cut offs in their closet! These shorts are perfect for spring break babe!
Fit & Features
- High rise waist
- Traditional five pocket and belt loop design
- Front button closure
- Light distressed detailing
- Cut off hem with slight fraying
- Denim fabric
Style Number/Barcode: 06603-0060
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Kailey High Rise Bermuda Denim Shorts
Oasis by Eunina
Summer can't come any sooner. Take a stylish cue and pair with your favorite bodysuit or a breezy blouse!
Fits & Features
- High Rise Fit
- Traditional Five Pocket Styling
- Belt Loop Design
- Button Waist I Zip Fly
- Destructed Detailing
- Skinny Leg Fit I Hits Mid Thigh I Raw Edge Hem
- Form Hugging Fit I Moderate Stretch
Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06603-0028
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Coastal Chic Linen Halter Maxi Dress
Meet your vacay soulmate. This breezy maxi serves minimal effort with major impact thanks to its sleek halter neckline, open tie back, and flowy fit made for golden hour strolls or rooftop cocktails.
Fit & Features
- Linen-blend woven fabric
- High halter neckline, spaghetti strap tie
- Open back with spaghetti strap tie, lower zipper and hook-eye closure
- High side slit
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000026
Category Name: Vacation Looks
Price: $11.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bring On The Floral Mini Dress
Bring on the bold floral with this absolutely adorable mini! The dress has a cute ruffle hem for major flirty vibes.
Fit & Features
- Tie shoulder straps
- Slight sweetheart neckline
- Parital stretchy smocked back
- Hidden zipper | Hook and eye closure
- High waist | Flowy short skirt | Ruffle hem
- Woven fabric | Woven lining | No stretch
- All over floral print
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0607
Category Name: Vacation Looks
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Darling Floral Chiffon Top
Keep it sweet in gorge florals! This charming top brings the romance with the lovely floral print!
Fit & Features
- Off The Shoulder Neckline | Built In No Slip Strip
- Plunging V-Neck Bust | Single Button Closure
- Built-In Flexible Boning | Long Sleeves
- Floral Print
- Sheer Lined Chiffon Fabric
- Relaxed Fit | Minimal Stretch
- Contrast Thong Bottom | Snap Button Closure
Style Number/Barcode: 06003-0333
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Got That Classic Vibe Jean Jacket
Get that classic vibe by layering on this perf basic jean jacket. A closet essential for sure.
Fit & Features
- Long sleeves | Single buttons to cuff
- Collared
- Button down front
- Two buttoned chest pockets
- Two vertical pockets at the waist
- Mid-length, form-fitting style
- Denim fabric | Minimal stretch
Style Number/Barcode: 06203-0055
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Jumping To Conclusions Denim Jumpsuit
Were going to go ahead and jump to the conclusion that you absolutely need a denim jumpsuit in your life! Talk about an easy outift!
Fit & Features
- Square neckline
- Spaghetti straps
- Criss cross back
- Low back design | Lower back zipper closure
- Straight leg
- Medium wash denim | Moderate stretch
- Slanted pockets
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06602-0092
Category Name: Vacation Looks
Price: $21.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Always Be My Baby Shimmering Blouse
Catch the moonlight on your date night in the most magical way! We are stunned over this beautiful blouse. Pair with high waist denim or a cute lil' mini skirt!
Fit & Features
- Sweetheart neckline
- Long balloon sleeves
- Cropped hemline
- Vertical princess seams
- Zipper closure center back + hook & eye closure
- Elastic wrist + Shoulder sleeve
- Woven knit with shimmering finish | Fully lined
Style Number/Barcode: 06003-0455
Category Name: Vacation Looks
Price: $11.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Rise Button Up Cut Off Jean Shorts
We all need that perfect pair of denim cut offs in our closet, and these high rise distressed shorts are a definite must have.
Fit & Features
- High rise waist
- Five button down front
- Five pocket and belt loop design
- Destructed detailing
- Frayed short hem
- Denim fabric | Moderate stretch
Style Number/Barcode: 06603-0031
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Smocked Over Florals Crop Top
Get smocked over this floral trend this season with a cute crop top!
Fit & Features
- Off The Shoulder Neckline
- Smocked Bodice
- Sheer Long Sleeves
- Floral Print
- Cropped Hem
- Relaxed Fit
- Moderate Stretch
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 06003-0387
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Eye Catcher Sparkling Denim Cropped Jacket
Add a touch of sparkle to your casual look! This cropped denim jacket is perfectly paired with all of your go-to high waist bottoms, and can easily be dressed up or down!
Fit & Features
- Collared neckline
- Long sleeves
- Button down front
- Double front pockets
- Light wash denim | No stretch
- Dusted in tiny rhinestone detailing
- Cropped raw hemline
Model is 5'9" with 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06203-0049
Category Name: Vacation Looks
Price: $17.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance