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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Bloom Babe Abstract Floral Mesh Corset Top
All eyes go straight to you in this blooming floral corset top that is both sweet and unapologetically bold. The structured mesh hugs your shape with that sculpted, confident fit you reach for on every hot-girl outing.
Shop Matching Bottoms: Bloom Babe Abstract Floral Mesh Maxi Skirt
Fit & Features
- Mesh fabric, high stretch
- Abstract floral print
- Strapless straight-across neckline
- Flexible boning
- Mid-length angled hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000143
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Golden Drift Beaded Statement Necklace
Bring effortless, earthy elegance to your look with this sculpted beaded statement necklace. Its mix of organic-shaped beads, tonal accents, and subtle texture gives off that soft-luxe vibe—like vintage coastal meets modern cool girl.
Fit & Features
- Assorted resin beads with organic, irregular shaping
- Round spacer beads and filigree-style accent beads
- Lobster clasp closure with adjustable extender chain
Style Number/Barcode: 07002-000351
Category Name: Vacation Looks
Price: $3.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Charm Check Tortoise Cat Eye Sunglasses
Serving instant trendy energy, these tortoise cat-eye sunnies come with tiny pearl charms that sway every time you turn your head—aka extra drama in the cutest way.
Fit & Features
- Tortoise cat-eye frame
- Pearl charm detailing at the temples
- Dark-tinted lenses
Style Number/Barcode: 07008-000102
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bold Blend Bracelet Set
A chic collision of glossy acrylic and gleaming gold makes this cuff the easiest way to elevate your wrist stack. Clean, modern, and a little unexpected—it’s the kind of piece that pulls your whole look together without saying a word.
Fit & Features:
- Mixed acrylic and metal cuff design
- Smooth sculpted silhouette
- High-shine gold accent
- Easy slip-on style
Style Number/Barcode: 07003-000215
Category Name: Vacation Looks
Price: $15.90
Availability: Out of Stock
Product Badge:- Ships Free
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Vibe Check Statement Stone Necklace Set
This necklace set shows up the way you wish every accessory would—bold, layered, and ready to elevate anything you throw on. The mixed textures and statement stone add that effortlessly chic vibe.
Fit & Features
- Two-pack necklace set
- Layered necklace design with mixed chain textures
- Faceted natural-style stone pendant at center
- Adjustable lobster clasp closures with extenders
Style Number/Barcode: 07002-000355
Category Name: Vacation Looks
Price: $24.90
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Crush Hoop Halter Crop Top
When you want to bring a little chaos—in the cute way—this halter crop top steps in with all the confidence of a bold-print moment. Light, flouncy, and ready for any night you decide to turn up the charm.
Shop The Matching Skort: Wild Crush Ruffle Mini Skort
Fit & Features
- Sheer mesh fabrication with animal print
- Strapless neckline with halter strap featuring dual gold-tone O-ring hardware
- Ruched bodice creating a fitted silhouette
- Cropped hemline
- Runs true to size
Style Number/Barcode: 06001-000379
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: RED
Available Size: S, M, L
Product Badge:- Part of a Set
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Bloom Boldly Flower Drop Earrings
These cascading flower drop earrings bring that soft-glam drama your outfit’s been craving. Lightweight and eye-catching, they add just the perfect touch of bold.
Fit & Features
- Drop earrings with a cascading floral design
- Acrylic petals with textured detailing
- Gold-tone centers for subtle contrast
- Lightweight construction for comfortable wear
- Post-back post closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000232
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Shoreline Shine Metal Shell Clutch
This sculpted shell clutch is your instant glam upgrade — glossy, dimensional, and impossible to ignore. It brings that luxe, vacation-meets-night-out energy no matter what you’re wearing.
Fit & Features
- Hard case shell silhouette
- Metallic high-shine finish
- Short detachable chain top handle
- Detachable crossbody chain strap
- Spacious interior
- Structured mini size
Style Number/Barcode: 07203-000127
Category Name: Vacation Looks
Price: $28.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Mael Floral Rhinestone Mermaid Formal Dress
Special Occasion
Designed to mesmerize from every angle, the Mael gown drapes the body in a dreamy floral print that feels both romantic and striking. The rhinestone-kissed halter V-neckline and sultry open back create a fluid, sculpted silhouette that moves with unforgettable elegance.
Fit & Features
- Mesh-lined fabric with floral print and rhinestone embellishment
- Halter V-neckline, spaghetti strap tie back closure, padded bra cups
- Open back with flattering ruched detailing
- Mermaid silhouette with floor-length hem
- Runs true to size
Where to Wear:
Weddings, destination vacations, resort dinners, upscale date nights, engagement parties, art museum soiree, birthday celebrations, cocktail parties
Style Number/Barcode: 05002-000750
Category Name: Vacation Looks
Price: $39.97 $84.90
On Sale: Yes
Availability: In Stock
Available Color: RED
Available Size: XS, S, L
Product Badge:- Sale
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Street Sleek Sunglasses
When you want that effortlessly cool vibe without even thinking about it, these everyday sunglasses do the work for you. Clean lines, a refined frame, and a just-right attitude make them the pair you grab on repeat.
Fit & Features
- Classic everyday silhouette
- Smooth curved temples
- Dark-tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000103
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty Intent Butterfly Side Sunglasses
Delicate but definitely noticed. These sunglasses add a subtle glam touch that feels elevated, effortless, and just extra enough for everyday styling.
Fit & Features
- Rimless lens design
- Butterfly side hardware detail
- Rubber nose supports
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000245
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BROWN, PURPLE
Available Size: NS
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Minimalist Sleek Oval Sunglasses
A chic little finishing touch that upgrades your whole mood. These oval sunglasses add a sleek, minimalist edge to any 'fit, from coffee runs to content strolls.
Fit & Features
- Oval frame design adds a sleek, minimalist touch
- Lightweight plastic frame construction
- Built-in nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000122
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: BROWN, BLACK
Available Size: NS
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Signature Vibe Square Sunglasses
These are the shades you wear when you want your vibe to speak first. The slim square silhouette adds that clean, modern edge you love for elevated 'fits and effortless daytime looks.
Fit & Features
- Rectangular metal frame
- Sleek, slim silhouette
- Dark-tinted lenses
- Adjustable rubber nose pads for customized comfort
- Lightweight construction
Style Number/Barcode: 07008-000124
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Vibe Tie-Front Bandeau Bikini Top
A little flirty, a little floaty—this tie-front bandeau bikini top brings soft glam with zero effort. The ruffled layer moves with you for that breezy, beach-dream vibe you’ll want in every sun-soaked moment.
Shop Matching Bottoms: Flirty Vibe V-Cut Bikini Bottoms
Fit & Features
- Strapless bandeau neckline with flyaway ruffle layer
- Center front tie detail for adjustable fit
- Smooth stretch knit fabric
- Cropped length
- Runs true to size
Style Number/Barcode: 07104-000011
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: IVORY
Available Size: L
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Flirty Vibe V-Cut Bikini Bottoms
Meet the bikini bottom that nails that effortless, flirty vibe without overthinking it. The sharp V-cut sculpts your shape and serves up that confident, beach-dream vibe you’ll want in every sun-soaked moment.
Shop Matching Top: Flirty Vibe Tie-Front Bandeau Bikini Top
Fit & Features
- V-cut front waist
- High-cut sides for a sleek, minimal look
- Cheeky back coverage
- Smooth stretch knit fabric
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000019
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: IVORY
Available Size: L
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Easy Days Raffia Buckle Slide Sandals
Slip on and step out, plans optional. These raffia buckle slide sandals keep things polished yet stylish, perfect for a destination vacation or strolling a beachside town.
Fit & Features
- 1" Low block heel for comfortable lift
- Open square toe
- Single wide strap across the vamp
- Decorative buckle detail
- Slip-on mule silhouette
- Raffia-textured upper
- Runs true to size
Style Number/Barcode: 07404-000043
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Mix It Up Three-Pack Hoop Earrings
Options are the vibe. This hoop earring trio gives you three distinct looks to rotate, stack, or style solo depending on the mood you’re in.
Fit & Features
- Polished metal and resin construction
- Classic hoop silhouettes in varied textures
- Three pair set for versatile styling
- Post back closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000243
Category Name: Vacation Looks
Price: $13.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Monroe Metallic Knit Mermaid Formal Dress
Special Occasion
The Monroe dress is made for evenings that linger, flowing effortlessly with a soft metallic knit that catches the light as you move. A plunge-wired halter neckline with a front sash and ruched mermaid silhouette creates a look that feels sculpted, graceful, and undeniably striking.
Fit & Features
- Metallic knit-lined fabric with moderate stretch
- Plunging V-neckline with underwire support
- Ruched detailing through bodice and hips
- Center front sash detail
- Back zipper and hook-eye closure
- Mermaid silhouette with floor-length hem
- Runs true to size
Where to Wear:
Destination weddings, galas, evening fundraisers, formal dinners, upscale receptions, evening ceremonies, resort vacations, honeymoons, milestone celebrations
Style Number/Barcode: 05002-000992
Category Name: Vacation Looks
Price: $89.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
Product Badge:- Ships Free
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Layton Mesh One Shoulder Mermaid Formal Dress
Special Occasion
Striking yet refined, the Layton mesh mermaid gown is designed for entrances that feel confident and considered. A one-shoulder neckline with hardware inset meets a sculpting side cutout, while the sheer floor-length hem adds fluid movement with a modern edge.
Fit & Features
- Mesh fabric, partial knit lining, sheer finish
- One-shoulder neckline with hardware inset detail
- Side cutout accented with coordinating hardware
- Sheer mermaid floor-length hem
- Runs true to size
Where to Wear:
Black-tie weddings, formal galas, red-carpet events, award nights, upscale destination weddings and receptions, luxury rooftop hotel soirees, city formal events, elegant evenings
Style Number/Barcode: 05002-001694
Category Name: Vacation Looks
Price: $69.90
Availability: In Stock
Available Color: WHITE, BLACK
Available Size: XS, S, M, L, XL
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Milana Velvet Open Back Mermaid Formal Dress
Special Occasion
The Milana dress is designed for evenings that feel refined yet undeniably captivating, blending rich flocked velvet with a silhouette that skims and sculpts. A V-neck front leads into a striking cutout tie open back, flowing into a mermaid floor-length shape made for polished entrances.
Fit & Features
- Burnout velvet fabric with floral pattern
- V-neckline with adjustable spaghetti straps
- Triangle bust with underbust twist detail
- Back zipper and hook-eye closure
- Side waist cutouts with open-back tie closure
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Weddings, black tie galas, elegant cocktail parties, celebrations, destination resorts, honeymoons, birthday dinners, fashion-forward occasions, red-carpet events
Style Number/Barcode: 05002-000530
Category Name: Vacation Looks
Price: $19.97 $89.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Sale
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Golden Blessings Charm Layered Necklace Set
Channel chic blessings with this charm-packed jewelry set featuring iconic pendants, dainty cross studs, and a sparkling chain bracelet. It's perfect for giving your look a radiant glow.
Fit & Features
- Mixed charm necklace with saint medallions, coin charms, and celestial details
- Lobster clasp closure
- Dainty cross stud earrings, post-back closure
- Rhinestone-trim chain bracelet, cross charm, adjustable slider bead
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07002-000319
Category Name: Vacation Looks
Price: $4.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Quiet Luxury Back Chain Body Jewelry
This is the kind of detail that changes the whole look without saying a word. Delicate chains drape just right, adding subtle shine and intention to open backs, low cuts, and barely-there moments.
Fit & Features
- Rhinestone accents along the neckline chain
- Multi-drop chain design for front and back styling
- Adjustable lobster clasp closure
Style Number/Barcode: 07002-000296
Category Name: Vacation Looks
Price: $15.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Soft Focus Shine Beaded Necklace
Low effort, high impact—the kind of necklace that pulls a whole look together without trying too hard. This layered rosary-style necklace adds just enough shine to sit perfectly against bare skin, plunging necklines, or your favorite going-out top.
Fit & Features
- Polished layered rosary-style necklace
- Beaded chain detailing with contrast accents
- Cross pendant drop design
- Lobster clasp closure
Style Number/Barcode: 07002-000362
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Sunlit Mood Crochet Triangle Bikini Top
The bikini top you reach for when you want effortless allure without overthinking it. The crochet wavy texture and triangle fit keep it flirty, lightweight, and ready for every sun-drenched plan.
Shop Matching Bottoms: Sunlit Mood Crochet Swim Shorts
Fit & Features
- Triangle cups with adjustable halter and back ties
- Sliding cup design for customizable coverage
- Crochet knit fabric with a multicolor wave pattern
- Runs true to size
Style Number/Barcode: 07104-000012
Category Name: Vacation Looks
Price: $25.90
Availability: Out of Stock
Product Badge:- Ships Free
- Triangle cups with adjustable halter and back ties