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
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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
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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: 07008-000315
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: TORTOISE
Available Size: NS
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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
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Fierce Aura Beaded Leopard Print Ruffle Romper
This romper is doing the most in all the right places. A plunging halter front is finished with beaded accents, while the mixed leopard and floral print keeps the look anything but predictable. The ruched waist and tiered ruffle overlay bring the whole thing together with hidden shorts underneath.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Mixed leopard and floral print pattern
- Sleeveless plunging neckline, beaded strap details
- Tie-back halter spaghetti straps
- Open back, lower tie-back spaghetti straps
- Ruched drop waist
- Tiered ruffle mini-length overlay with flared fit, hidden built-in shorts
- Runs true to size
Style Number/Barcode: 06503-000441
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Shine On Chunky Sequin Mini Skort
Let the sequins handle the statement. This mini skort brings all-over chunky shine to a fitted shape with built-in shorts for a look that already feels styled. Pair it with a sleek top and minimal accessories to keep the sparkle front and center.
Fit & Features
- Woven fabric
- All-over chunky sequin embellishment
- Mid-rise waist
- Hidden side zipper closure
- Mini-length overlay, fitted silhouette
- Hidden built-in knit shorts
- Runs true to size
Style Number/Barcode: 06403-000221
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: BLUE
Available Size: S, M, L
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Steal Attention Open Back Maxi Dress
This maxi dress deserves its own moment. The lurex knit fabric catches the light from every angle, while the plunge halter neckline, open back, and high side slit keep the whole look unapologetically bold.
Fit & Features
- Lurex knit fabric, knit lining
- Plunge halter neck, tie straps
- Open back with dual adjustable straps
- High side slit
- Form-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-001208
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
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