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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Breezy Strapless Drop Waist Maxi Dress
The silhouette does all the work. This strapless maxi dress pairs a fitted bodice with an asymmetrical drop waist and a flowy chiffon skirt for a sleek-to-soft silhouette. Perfect for dressy date nights, vacations, and weekend plans.
Fit & Features
- Lined crepe and chiffon fabrication
- Strapless neckline
- Fitted crepe bodice with asymmetrical drop waist
- Flowy chiffon maxi-length hem
- A-line fit
- Runs true to size
Style Number/Barcode: 05101-001447
Category Name: Vacation Looks
Price: $64.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Tess Lace Up Floral Mermaid Formal Dress
Special Occasion
Bold florals are taking a more sculpted direction. The Tess mesh mermaid dress pairs an oversized print with a fitted floor-length shape and lace-up back for a streamlined take on the trend. Delicate straps keep the look light and balanced.
Fit & Features
- Printed mesh fabrication, smooth lining
- V-neckline with spaghetti straps
- Lace-up open back
- Mermaid silhouette
- Floor-length hem
- Runs true to size
Where to Wear:
Destination celebrations, honeymoons, vacations, bachelorettes, birthday dinners, yacht parties, date nights, cocktail parties
Style Number/Barcode: 05002-001677
Category Name: Vacation Looks
Price: $69.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival