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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Butterfly Effect Rhinestone Body Chain
Butterflies just got a little more dressed up. This rhinestone body chain drapes delicate chains across the neckline and waist with a crystal butterfly centerpiece for a flirty finish made for plunging tops, minis, and going-out looks.
Fit & Features
- Delicate metal chain construction
- Rhinestone-embellished butterfly centerpiece
- Draped body chain silhouette
- Adjustable neck and waist chain closures
Style Number/Barcode: 07002-000566
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
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Pattern Play Chevron Knit Halter Top
Pattern play with a little edge. This chevron knit halter top hugs the figure with a V-neckline, open back, and tie-back straps made for pairing with denim, minis, and everything in between.
Fit & Features
- Knit fabric
- Chevron pattern
- Sleeveless V-neckline
- Tie-back halter straps
- Open back
- Mid-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000658
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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Plans In Motion Oversized Aviator Sunglasses
The kind of shades that make the whole outfit. These oversized aviator sunglasses bring a sleek retro shape with tinted lenses that work for coffee runs, weekend plans, and sunny days.
Fit & Features
- Oversized aviator silhouette
- Tortoise pattern
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000316
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
Product Badge:- New Arrival
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Vacation Pending Three Pack Hibiscus Hair Clips
Your updo just booked the fun plans. This three-pack of hibiscus hair clips brings glossy floral dimension to buns, twists, and effortless claw clip moments when your hair needs a little extra personality.
Fit & Features
- Three-pack hair clip set
- Glossy hibiscus flower design
- Dimensional petal detailing
- Claw clip closure
Style Number/Barcode: 07006-000195
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: MULTI
Available Size: NS
Product Badge:- New Arrival