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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Handpicked Sparkle Hand Chain
Florals, but make them extra polished. This rhinestone hand chain links a delicate bracelet to a statement ring for a gorgeous look with your semi-formal or special occasion dress.
Fit & Features
- Delicate chain hand bracelet design
- Rhinestone floral accents
- Attached chain with coordinating ring
- Lobster clasp closure
- Polished shine
Style Number/Barcode: 07003-000290
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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Shimmer Status Sequin Beaded Mini Skirt
Consider the entrance handled. This sequin beaded mesh mini skirt features a form-hugging fit, adding just enough shimmer for dinner reservations, parties, and RSVP plans. Pair with the matching poncho.
Shop Matching Top: Shimmer Status Sequin Beaded Mesh Poncho
Fit & Features
- Sheer mesh fabric with knit lining, moderate stretch
- Floral sequin and beaded swirl embroidery
- High-rise waist
- Mini-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06501-000176
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: TAUPE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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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
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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
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Booked For Trouble Mixed Print Ruffle Romper
Cute plans just got a little less predictable. This mixed print romper pairs a plunging halter neckline, open back, and layered ruffles for a flirty going-out look that moves like a mini dress with built-in confidence.
Fit & Features
- Lightweight printed fabric with a flowy feel
- Halter neckline with plunging front
- Open back with adjustable tie closure
- Layered ruffle shorts with draped side detail
- Cheeky coverage
- Runs true to size
Style Number/Barcode: 06503-000428
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: PLUM
Available Size: XS, S, M, L
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Modern Textured Bodycon Mini Dress
The styling is simple, but the details are not. This bodycon mini dress combines textured knit, a scoop halter neckline, and a double-twist open back for a clean look with extra interest. Add a metallic bag and heels to finish it off.
Fit & Features
- Textured knit fabric with stretch
- Scoop halter neckline
- Double-twist open back
- Bodycon mini-length fit
- Runs true to size
Style Number/Barcode: 06005-000433
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: XS, S, M, L
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Bloom Rush Floral Print Off-The-Shoulder Top
Prints that refuse to blend in. This floral and animal multi-print off-the-shoulder top mixes mesh, twisted detailing, and a form-hugging cropped fit for a look that instantly makes night-out styling feel more interesting. Pair with the matching mini skort.
Shop Matching Bottoms: Bloom Rush Floral Print Ruffle Mini Skort
Fit & Features
- Mesh fabric with knit lining, high stretch
- Floral and animal multi-print pattern
- Asymmetric off-the-shoulder neckline
- Tank shoulder straps, twisted detail
- Cropped hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000286
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Beach Club Darling Beaded Bra Top
This isn't just a top—it's the perfect statement piece to wear on vacay. Covered in intricate beads, shell accents, and delicate chain details, this halter bra top was made for beach clubs, tropical resorts, and sunset dinners by the water.
Fit & Features
- Beaded embellished knit fabric, lined bust
- Halter sweetheart neckline, tie straps
- Shell and dainty chain accents
- Dual tie-back design
- Bra top silhouette
- Runs true to size
Style Number/Barcode: 06001-000625
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge: -
Nicole Beaded Slit Long Formal Dress
Special Occasion
Sleek, sculpted, and made for a room full of double takes, the Nicole slinky gown knows exactly how to make an entrance. The V neckline, beaded straps, waist cutouts, and double-slit slim silhouette bring a sultry finish with polished special occasion drama.
Fit & Features
- Slinky knit fabric, smooth knit lining, high stretch
- V-neckline, beaded adjustable spaghetti straps
- Back zipper and hook-eye closure
- Side waist cutouts with beaded strappy design
- Dual high-side slits
- Curve-hugging long-length silhouette
- Runs true to size
Where to Wear:
Vacations, honeymoons, resort getaways, destination celebrations, birthday dinners, date nights
Style Number/Barcode: 05002-001638
Category Name: Vacation Looks
Price: $69.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Stacked Intentions Bangle Bracelet Set
Your wrist stack, already curated. This three-piece bangle set mixes sleek metal with glossy resin and studded accents for an easy layered look that feels polished with a little edge.
Fit & Features
- Metal and resin construction
- Three-piece bangle bracelet set
- Mixed smooth and studded finishes
- Stackable slip-on design
Style Number/Barcode: 07003-000347
Category Name: Vacation Looks
Price: $16.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
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Petal Power Floral Statement Stud Earrings
Florals, but make them jewelry. These statement stud earrings feature sculpted petal details and a dimensional floral shape that adds a polished finish to brunch looks, date nights, or dressier plans.
Fit & Features
- Metal floral construction
- Sculpted petal design
- Dimensional statement stud silhouette
- Post back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000483
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Booked Until Sunset Aviator Sunglasses
A little retro, a lot polished. The oversized aviator silhouette and tinted lenses bring an effortlessly cool finish to everything from denim days to weekend plans.
Fit & Features
- Glossy frame silhouette
- Oversized aviator silhouette
- Tinted lenses with 100% UV protection
- Wide bridge with sculpted designs
Style Number/Barcode: 07008-000311
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Plans Look Better Rectangular Sunglasses
These sunglasses feature a slim rectangular frame and tinted lenses that bring a sleek throwback edge that works with any outfit.
Fit & Features
- Slim rectangular silhouette
- Tinted lenses
- 100% UV protection
- Rubber nose supports
- Sleek metal arms
Style Number/Barcode: 07008-000314
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
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Too Busy Looking Good Aviator Sunglasses
These oversized aviator sunglasses bring a sleek statement with tinted lenses and a bold wraparound-inspired silhouette made for coffee runs, road trips, and plans that somehow became all day.
Fit & Features
- Oversized aviator silhouette
- Tinted lenses
- Sleek metal arms
- 100% UV protection
Style Number/Barcode: 07008-000312
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
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No Photos Please Shield Sunglasses
These shades understood the assignment without trying too hard. The curved shield-inspired shape and narrow silhouette bring a sleek Y2K edge that instantly sharpens off-duty looks.
Fit & Features
- Glossy frame silhouette
- Shield design
- Tinted lenses with 100% UV protection
- Sculpted side accent
- Sleek metal arms
Style Number/Barcode: 07008-000313
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
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Escape Route Printed Cowl Halter Crop Top
Booked for somewhere better. This mixed animal and floral print halter crop top pairs a draped cowl neckline with an open tie back for an easy vacay look that feels flirty without trying too hard.
Shop Matching Skort: Escape Route Printed Ruffle Skort
Fit & Features
- Lightweight printed mesh
- Cropped halter silhouette
- Draped cowl neckline
- Open back with tie closure
- Animal and tropical floral pattern
- Runs true to size
Style Number/Barcode: 06001-000861
Category Name: Vacation Looks
Price: $22.90
Availability: In Stock
Available Color: PINK
Available Size: M, L
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Escape Route Printed Ruffle Skort
This is the kind of matching set that basically plans the outfit for you. The mixed animal and tropical floral printed ruffle skort features built-in shorts, tiered flounces, and cascading side drapes made for resort nights and weekend plans.
Shop Matching Top: Escape Route Printed Cowl Halter Crop Top
Fit & Features
- Lightweight printed mesh
- Low-rise skort silhouette
- Tiered ruffle overlay
- Animal and tropical floral pattern
- Built-in shorts with cascading side drapes
- Runs true to size
Style Number/Barcode: 06503-000459
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: PINK
Available Size: S, M, L
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Tropic Crush Hibiscus Claw Clip
Vacation hair, handled. This crystal hibiscus claw clip brings the sparkle with a statement flower design that makes messy buns, twists, and quick updos look way more intentional.
Fit & Features
- Smooth molded construction
- Hibiscus flower design with crystal embellishments
- Statement dimensional petals
- Claw clip closure for an easy, secure hold
Style Number/Barcode: 07006-000198
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: PINK, BURGUNDY, CHARTREUSE
Available Size: NS
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Bloom Rush Floral Print Ruffle Mini Skort
Prints that refuse to blend in. This floral and animal multi-print mini skort mixes mesh, ruffled detailing, and a flirty, flowy fit for a look that instantly makes night-out styling feel more interesting. Pair with the matching crop top.
Shop Matching Top: Bloom Rush Floral Print Off-The-Shoulder Top
Fit & Features
- Mesh fabric, high stretch
- Floral and animal multi-print pattern
- Mid-rise waist
- Mini-length tiered ruffled hem, A-line fit
- Tie detail, side slit
- Hidden built-in knit shorts
- Runs true to size
Style Number/Barcode: 06503-000432
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Island Heat Beaded Body Chain
Vacation attitude, zero plane ticket required. Layered beads, delicate chainwork, and dimensional stone details drape the body with a tropical pop-star-inspired finish made for festivals, pool parties, and concerts.
Fit & Features
- Multi-colored beaded chain design
- Draped body-framing silhouette
- Charm accents
- Dual lobster clasp closures
Style Number/Barcode: 07002-000770
Category Name: Vacation Looks
Price: $54.90
Availability: In Stock
Available Color: TURQUOISE
Available Size: NS
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Made To Be Seen Beaded Body Chain
No permission needed, just add confidence. Draped beads, layered chains, and dangling charms bring a bold Latin pop-inspired finish made for concerts, festivals, and outfits that refuse to play backup.
Fit & Features
- Multi-colored beaded body chain
- Charm accents
- Chain designs
- Dual lobster clasp closures
Style Number/Barcode: 07002-000771
Category Name: Vacation Looks
Price: $54.90
Availability: Out of Stock
Product Badge:- Ships Free
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Tropic Temptation Beaded Body Chain
Consider this your outfit’s plus one. Layered beads and draped chain details create a bold, body-framing design perfect for concerts, festivals, and beach parties.
Fit & Features
- Multi-colored bead chain design
- Layered body-framing silhouette
- Lobster clasp closures
Style Number/Barcode: 07002-000769
Category Name: Vacation Looks
Price: $54.90
Availability: In Stock
Available Color: GREEN
Available Size: NS
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Elevated Look Faux Leather Wedge Sandals
Consider your outfit officially elevated. These faux leather wedge sandals pair a sculpted heel with a thong strap and open almond toe for an easy statement with minis, denim, or going-out looks.
Fit & Features
- Wedge heel
- Open almond-shaped toe
- Thong strap design
- Open back, easy on-and-off styling
- Faux leather material
- Runs true to size
Style Number/Barcode: 07406-000077
Category Name: Vacation Looks
Price: $28.90
Availability: In Stock
Available Color: BLACK
Available Size: 5.5, 6, 6.5, 7, 7.5, 10
Product Badge:- Best Seller
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Coastal Crush Starfish Statement Necklace
Beachy, but nowhere near basic. This starfish statement necklace pairs a bold sculptural pendant with layered mesh strands for an elevated coastal finish that instantly upgrades plunging necklines, dresses, and vacation looks.
Fit & Features
- Layered mesh strand construction
- Oversized sculptural starfish pendant
- Statement necklace silhouette
- Lobster clasp with adjustable chain extender
Style Number/Barcode: 07002-000693
Category Name: Vacation Looks
Price: $19.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
