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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Blooming Agenda Floral Mesh Strapless Bustier
Booked, busy, and somehow still best dressed. This floral mesh bustier brings sculpted structure and a flattering fit that pairs perfectly with the matching skirt for any RSVP-worthy plan on your calendar.
Shop Matching Bottoms: Blooming Agenda Floral Mesh Maxi Skirt
Fit & Features
- Mesh fabric, high stretch
- Large floral print
- Strapless straight-across neckline
- Flexible boning
- Lace-up back design with tie closure
- Mid-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000693
Category Name: Vacation Looks
Price: $36.90
Availability: Out of Stock
Product Badge:- Ships Free
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Palm Paradise Halter Romper
Booked the trip, found the outfit. This tropical leaf print romper combines a plunging halter neckline, bead accents, and a flirty open tie back with a tiered ruffle hem made for vacations, resort destinations, and weekend escapes.
Fit & Features
- Palm print, mesh fabric, knit lining
- Plunge halter neckline, beaded strap, tie straps
- Open tie-back
- Tiered ruffle mini-length hem
- Built-in shorts lining
- Runs true to size
Style Number/Barcode: 06503-000307
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Blooming Agenda Floral Mesh Maxi Skirt
Booked, busy, and somehow still best dressed. This floral mesh maxi skirt brings a high-cut back slit and a curve-hugging fit that pairs perfectly with the matching bustier for any RSVP-worthy plan on your calendar.
Shop Matching Top: Blooming Agenda Floral Mesh Strapless Bustier
Fit & Features
- Mesh fabric with full-length knit lining, high stretch
- Large floral print
- High-rise waist
- High-cut back slit
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06501-000183
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Polished Bloom Wrap Flower Arm Cuff
The arm cuff accessory that makes a simple outfit look styled in seconds. Featuring a wrap silhouette with sculpted floral accents, this arm cuff brings a romantic, fashion-forward feel to everything from vacation looks to special occasion dresses.
Fit & Features
- Metal wrap-around design
- Flower accents with rhinestone-embellished center insets
- Polished finish
Style Number/Barcode: 07003-000241
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: SILVER
Available Size: NS
Product Badge:- New Arrival
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Pretty Shine Layered Stone Belly Chain
Tiny details, major outfit payoff. This layered stone belly chain adds the prettiest shine to low-rise denim, bikinis, matching sets, and every last minute “wait… this actually eats” look.
Fit & Features
- Two-row layered cross-over design
- Dainty chains
- Clear stone accents
- Lobster clasp closure with extender
- Adjustable fit
Style Number/Barcode: 07002-000446
Category Name: Vacation Looks
Price: $11.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
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Caught Up Beaded Crop Top
The top that makes every mirror selfie worth posting. This crop top brings just the right amount of shine, serving a flattering curve-hugging fit and a striking open back that keeps all eyes on you.
Shop Matching Bottoms: Caught Up Beaded Maxi Skirt
Fit & Features
- Slinky knit stretchy fabric
- Plunge halter neckline
- Strappy beaded embellished open back
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000694
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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On Repeat Layered Stone Belly Chain
A little sparkle at the waist changes the whole outfit. This layered stone belly chain brings just enough shimmer to low-rise denim, swim looks, and going-out 'fits.
Fit & Features
- Two-row layered cross-over design
- Dainty chains
- Clear stone accents
- Lobster clasp closure with extender
- Adjustable fit
Style Number/Barcode: 07002-000443
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival