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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Brunch Bound Ruffle High-Low Maxi Skirt
Light, airy, and ready for wherever the day decides to go. This ruffle maxi skirt brings an effortless, breezy feel with its lightweight woven fabric and high-low flowy fit that's made for weekend brunch with your girls. Style with the matching cropped vest.
Shop Matching Top: Brunch Bound Tie-Front Cropped Vest
Fit & Features
- Lightweight woven fabric
- High-rise waist
- Maxi-length hem with flowy high-low silhouette
- Ruffled design
- Runs true to size
Style Number/Barcode: 06301-000011
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Palm Breeze Beaded Halter Top
The kind of top that makes every destination feel a little more glamorous. Designed with a curve-skimming fit, halter neckline, and beaded chain detail, this top brings effortless drama to beach dinners, resorts, and every plan in between.
Shop The Matching Skirt: Palm Breeze Beaded Maxi Skirt
Fit & Features
- Slinky knit double-lined stretchy fabric
- Halter neckline with beaded straps
- Fitted mid-length hem
- Runs true to size
Style Number/Barcode: 06001-000522
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Palm Breeze Beaded Maxi Skirt
The kind of skirt that makes every destination feel a little more glamorous. Designed with a curve-skimming fit, thigh-high slit, and beaded chain detail, this maxi skirt brings effortless drama to beach dinners, resorts, and every plan in between.
Shop The Matching Top: Palm Breeze Beaded Halter Top
Fit & Features
- Slinky knit double-lined stretchy fabric
- High-rise waist with detachable beaded swag chain
- Thigh-high slit
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 06501-000135
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Villa Nights Halter Crop Top
The kind of outfit that makes every entrance stunning. This halter crop top features a plunging neckline, open back, and beaded accents that effortlessly go from vacation dinners to special occasion plans.
Shop The Matching Skirt: Villa Nights High Slit Maxi Skirt
Fit & Features
- Slinky knit double-lined knit stretchy fabric
- Plunge halter neckline, beaded accents, tie straps
- Open back
- Fitted crop hem, side ruched seams
- Runs true to size
Style Number/Barcode: 06001-000688
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Charming Sweet Polka Dot Mini Dress
This polka dot mini dress was for the kind of getaway where your camera roll fills up before noon. With a draped halter neckline, and flirty sash details, this dress is ready for hotel brunches and strolling downtown.
Fit & Features
- Polka dot print, mesh fabric, smooth lining
- V-neckline
- Form-hugging fit
- Sash detailing
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000723
Category Name: Vacation Looks
Price: $44.90
Availability: Out of Stock
Product Badge:- Ships Free
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Checking In Chiffon Mini Dress
This ruffle chiffon mini dress was made for resorts, celebrations, and every vacation photo that somehow becomes your favorite. Just add sandals and oversized sunnies.
Fit & Features
- Chiffon fabric, smooth lining
- Square neckline
- Spaghetti straps
- Ruffled A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001178
Category Name: Vacation Looks
Price: $54.90
Availability: Out of Stock
Product Badge:- Ships Free