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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Simply Elevated Cork Wedges
Simply elevated is the vibe. These cork wedges pair a knotted woven toe strap with slim adjustable ankle straps and the luxe fit cushioned insole for polished height that moves from brunch to rooftop plans with ease.
Fit & Features
- Cork wedge heel
- Open almond-shaped toe
- Woven toe strap with knot design
- Thin adjustable ankle straps, buckle closure
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07406-000037
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: IVORY
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge:- New Arrival
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Rare Find Animal Print Maxi Dress
A little wild, a little glamorous, and impossible to scroll past. This animal print mesh maxi dress pairs a sweetheart neckline, cutout details, hardware accents, and a dramatic front sash for the kind of entrance people remember.
Fit & Features
- Multi-animal print, lined mesh fabric
- Strapless sweetheart neckline
- Hardware bust insert with cascading sash
- Cutout bodice
- Curve-hugging, maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000803
Category Name: Vacation Looks
Price: $54.90
Availability: Out of Stock
Product Badge:- Ships Free
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Catherine Crochet Cutout Formal Dress
Special Occasion
Sunset plans, destination energy, and a dress that knows exactly how to make an entrance. This crochet mermaid gown brings the drama with a plunging halter neckline, waist cutouts, beaded accents, and fringe trim made to move with you.
Fit & Features
- Crochet knit fabric
- Plunging halter neckline
- Waist cutout design
- Beaded tie front accents
- Mermaid silhouette
- Floor-length hem
- Runs true to size
Where to Wear:
Destination weddings, honeymoons, resort getaways, vacations, cruises, yacht parties, sunset cocktail events, date nights, birthday dinners
Style Number/Barcode: 05002-001605
Category Name: Vacation Looks
Price: $99.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sunset Spritz Multi-Print Ruffle Mini Skort
Pool plans, brunch plans, “wait where are we going next?” plans. This multi-print ruffle mini skort brings the flirty vibe with a flouncy hem, low-rise fit, and hidden shorts.
Fit & Features
- Knit fabric, high stretch
- Floral and animal multi-print pattern
- Low-rise waist, ruched detailing
- Side ruffled accents
- Tiered ruffled mini-length hem, A-line fit
- Hidden built-in shorts
- Runs true to size
Style Number/Barcode: 06503-000327
Category Name: Vacation Looks
Price: $34.90
Availability: Out of Stock
Product Badge:- Ships Free
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Jailene Cutout Coin Charm Formal Dress
Special Occasion
Designed for the girl who never blends into the background, the Jailene formal dress is all about movement, shimmer, and statement-making confidence. Crafted from sleek slinky fabric, this halter mermaid gown features dramatic cutouts, a thigh-high slit, and cascading coin embellishments that catch the light with every step, dance, and slow-motion entrance.
Fit & Features
- Slinky knit stretchy fabric
- Halter neckline, tie straps
- Partial open
- Cutout bodice with coin charm trimmed straps
- High side slit
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Vacations, honeymoons, resort getaways, destination celebrations, birthday dinners, yacht parties
Style Number/Barcode: 05002-001779
Category Name: Vacation Looks
Price: $79.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Ships Free