Vacation Looks

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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.

  • Sunlit Mood Crochet Swim Shorts

    The swim shorts you slip into when you want that effortless confidence. The crochet wavy texture and swim short fit keep it flirty, lightweight, and ready for every sun-drenched plan.

    Shop Matching Top: Sunlit Mood Crochet Triangle Bikini Top

    Fit & Features

    • Low-rise waist
    • Crochet knit fabric with a multicolor wave pattern
    • Swim short silhouette
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000020

    Category Name: Vacation Looks

    Price: $25.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: L

    Product Badge:
    • Part of a Set
  • Blake Sequin Payette One Shoulder Formal Dress

    Special Occasion

    Designed for the kind of entrance that feels polished yet impossible to forget, the Blake sequin payette dress moves with a soft shimmer and confident ease. A one-shoulder neckline with dual spaghetti straps meets a cutout bodice with a hardware hoop insert and a high side slit, creating a form-hugging long silhouette made for every elevated RSVP.

    Fit & Features

    • Allover sequin payette embellishments with smooth-lined interior
    • One-shoulder neckline with dual adjustable spaghetti straps
    • Cutout bodice with a hardware hoop insert at the waist
    • Dual side zippers and hook-eye closures
    • High side slit for movement and leg-lengthening effect
    • Form-hugging long silhouette
    • Runs true to size

     

    Where to Wear:

    Destination weddings, bridal celebrations, galas, upscale cocktail receptions, special date nights, anniversaries, honeymoons, resort vacations, dinner parties, birthdays

    Style Number/Barcode: 05002-001025

    Category Name: Vacation Looks

    Price: $39.97 $84.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lily Abstract Print Mermaid Formal Dress

    Special Occasion

    The Lily dress is made for nights that feel artful and unforgettable, where every detail deserves attention. A multi-print abstract fabric shapes a form-hugging long silhouette, finished with a sweetheart neckline, cutout bust, and a high side slit that brings movement and allure.

    Fit & Features

    • Abstract print, mesh-lined fabric with stretch
    • Adjustable spaghetti straps with sweetheart neckline and twist-front bust detail
    • Front cutout at bodice, padded bra cups
    • Back zipper and hook-eye closure
    • Ruched mesh overlay through bodice and skirt
    • High front slit at hem, floor-length mermaid silhouette
    • Runs true to size

     

    Where to Wear:

    Destination weddings, evening ceremonies, dressy cocktail parties, birthday dinners, engagement parties, fashion forward events, anniversaries, honeymoons, vacations

    Style Number/Barcode: 05002-000573

    Category Name: Vacation Looks

    Price: $69.90

    Availability: In Stock

    Available Color: RED-2

    Available Size: XS, S, M, L, XL

  • Hollie Floral Halter Mermaid Formal Dress

    Special Occasion

    Designed to command attention from every angle, the Hollie mesh mermaid dress pairs a statement floral print with a halter keyhole neckline for a look that feels both sculptural and fluid. The open back and floor-length finish create an unforgettable balance of drama and refinement.

    Fit & Features

    • Mesh-lined fabric with all-over floral print
    • Halter neckline with deep V-shaped keyhole cutout
    • Twist-front bust with ruched detailing
    • Open back with adjustable halter tie
    • High-waist seam for a contoured fit
    • Floor-length mermaid silhouette
    • Runs true to size

     

    Where to Wear:

    Weddings, destination resorts, honeymoons, birthday dinners, dressy cocktail parties, gala dinners, engagement parties, rehearsal dinners, black tie occasions

    Style Number/Barcode: 05002-001156

    Category Name: Vacation Looks

    Price: $74.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Booked the Getaway Crop Top

    This top already feels like a destination. With a form-hugging fit, statement hardware, and a skin-baring cutout that moves when you do, it’s made for warm nights and last-minute getaways. 

    Shop The Matching Skirt: Booked the Getaway Maxi Skirt

    Fit & Features

    • Lightweight mesh-lined fabric with printed finish
    • Halter sweetheart neckline with hardware accent
    • Spaghetti strap ties
    • Cutout underbust design
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000388

    Category Name: Vacation Looks

    Price: $29.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Off Duty Attitude Cat Eye Sunglasses

    These are the sunglasses you reach for when your outfit already says enough. Sleek cat eye frames with a subtle edge make every look feel intentional, even on no-plan days.

    Fit & Features

    • Lightweight plastic frame
    • Cat eye silhouette
    • Tinted lenses
    • Slim metal arms
    • 100% UV protection

    Style Number/Barcode: 07008-000106

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunkissed Round Metal Sunglasses

    Meet the retro-inspired round sunnies that instantly give every outfit that effortlessly-cool, “I just landed in Ibiza” vibe. The slim metal frames and tinted lenses keep things minimal but totally magnetic.

    Fit & Features

    • Lightweight metal round frames
    • Slim arms with comfortable ear tips
    • Tinted lenses
    • Rubber nose supports
    • 100% UV protection

    Style Number/Barcode: 07008-000107

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bare It Bold Halter Mini Dress

    This one doesn’t wait for an invite. A barely-there halter with bold cutouts and an O ring detail that knows exactly what it’s doing—made for warm destinations and sunset dinners.

    Fit & Features

    • Soft ribbed fabric with a slinky feel
    • Triangle halter neckline with tie straps
    • O ring center with waist cutout detail
    • Mini-length skirt with ruffle hem
    • Runs true to size

    Style Number/Barcode: 05102-000389

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: XS, S, M, L

  • Golden Hour Drama Leaf Earrings

    All the drama, zero effort. These sculptural leaf earrings catch the light with every move and instantly upgrade even the simplest look.

    Fit & Features

    • Lightweight metal with textured finish
    • Statement drop silhouette with organic leaf shape
    • Post back closure

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-000289

    Category Name: Vacation Looks

    Price: $16.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Chic Stack Five Piece Bangle Bracelet Set

    More is more, babe. This five-piece bangle bracelet set makes stacking look effortless with its mix of textures and metallic finishes. Wear them solo for a subtle shimmer or all at once for that “I planned this” kind of energy.

    Fit & Features

    • Five-piece bangle bracelet set
    • Mixed textures and finishes
    • Stackable design

    Style Number/Barcode: 07003-000104

    Category Name: Vacation Looks

    Price: $13.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Finishing Touch Three-Pack Earring Set

    These are the kind of earrings that pull everything together without trying too hard. A mixed hoop set with warm stone details that feels styled, balanced, and very much on purpose.

    Fit & Features

    • Set of three hoop earring pairs with stud accents
    • Polished metal base with tiger eye stone detailing
    • Mix of stud and hoop silhouettes
    • Secure post-back and hinge closures

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-000240

    Category Name: Vacation Looks

    Price: $13.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Soft Shine Layered Chain Necklace

    Effortless shine, zero overthinking—this layered necklace brings together smooth gold discs on delicate chains for that modern, polished vibe. It’s the piece you throw on when you want your outfit to feel instantly put-together without trying too hard.

    Fit & Features

    • Layered chain
    • Disc charms
    • Mixed textures
    • Lobster clasp closure

    Style Number/Barcode: 07002-000298

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Instant Impact Statement Stud Earrings

    Bold shape, effortless polish. These hammered circle stud earrings add just enough texture to make your look feel intentional, even when you got dressed in five minutes.

    Fit & Features

    • Textured metal with a hammered finish
    • Oversized circle statement stud silhouette
    • Flat silhouette
    • Post back closure 

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-000277

    Category Name: Vacation Looks

    Price: $4.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stack The Shine Beaded Stretch Bracelet Set

    When your outfit needs a little extra glow, this bracelet set comes through like it was made for the moment. Each beaded stretch bracelet adds its own texture and shine, creating a stack that is trendy and chic.

    Fit & Features

    • Set of five mixed-shape beaded stretch bracelets
    • Polished high-shine finish
    • Easy slip-on styling
    • Flexible fit for various wrist sizes

    Style Number/Barcode: 07003-000156

    Category Name: Vacation Looks

    Price: $14.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sculpted Swirl Statement Earrings

    These circle wave earrings are the kind of statement that feels intentional, not loud — sculpted, fluid, and designed to elevate anything from a sleek bun to your go-to blowout. They’re bold without trying too hard.

    Fit & Features

    • Sculpted circle wave silhouette
    • Lightweight statement design
    • Polished finish
    • Post-back closure

     

    Earrings are final sale and may not be returned or exchanged

    Style Number/Barcode: 07001-000290

    Category Name: Vacation Looks

    Price: $3.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Artsy Chic Statement Pendant Necklace

    When you want something low-effort but high-impact, this pendant necklace steps in and steals the room. The hammered metal and smooth faux leather cord bring that effortlessly artsy vibe that works from coffee catch-ups to late-night plans.

    Fit & Features

    • Hammered metal pendant with an open-circle shape
    • Smooth faux-leather cord
    • Lightweight construction
    • Tie-back closure

    Style Number/Barcode: 07002-000346

    Category Name: Vacation Looks

    Price: $4.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Golden Spotlight Plunge Long Sleeve Maxi Dress

    Bring the drama and the dazzle. This luxe long sleeve maxi dress mixes a sultry plunge with a draped overlay and a bold statement hardware accent that instantly steals the spotlight.

    Fit & Features

    • Smooth knit stretch fabric
    • Plunge cowl neckline
    • Halter bralettes accent with hardware insets
    • Fitted long sleeves
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000784

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Bold Plans Tropical Floral Mini Tube Dress

    A floral moment that knows it’s being noticed. This tropical floral mini tube dress hugs you in all the right places with a smooth, stretchy feel that’s made for warm nights, bold plans, and outfits that don’t blend in.

    Fit & Features

    • Smooth knit fabric, sewn-in lining
    • High stretch for a body-hugging fit
    • Large-scale tropical floral print
    • Strapless straight-across neckline
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000413

    Category Name: Vacation Looks

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Catrina Crochet Slit Formal Dress

    Special Occasion

    Designed for destination moments that call for understated allure, the Catrina crochet column dress feels both romantic and refined. A strapless sweetheart neckline meets a sculptural hardware cutout and high side slit, creating a silhouette that feels effortless, modern, and perfectly bridal for sun-soaked celebrations.

    Fit & Features

    • Crochet fabric lined with mesh
    • Strapless sweetheart neckline with hardware insert, padded bra cups
    • Keyhole cutout
    • Tie-back detail, zipper and hook-eye closure
    • High side slit for movement
    • Curve-hugging column silhouette
    • Floor-length hem
    • Runs true to size

     

    Where to Wear:

    Destination weddings, bridal rehearsal dinners, bachelorette trips, tropical resorts, sunset cocktail parties, honeymoons, upscale beachside restaurants, weekend getaways

    Style Number/Barcode: 05002-001128

    Category Name: Vacation Looks

    Price: $69.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Poolside Proof Hoop Detail Bandeau Bikini Top

    This one hits before you even hit the water. The bandeau halter bikini top features a clean metal accent for a trendy vibe made for sun-soaked plans. Pair with the matching bottoms.

    Shop The Matching Bottoms: Poolside Proof High-Cut Bikini Bottoms

    Fit & Features

    • Sleek knit-lined fabric
    • Bandeau halter-style neckline with ties
    • Removable padding
    • Hoop insert
    • Runs true to size

    Style Number/Barcode: 07104-000015

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: PINK

    Available Size: M, L

  • Poolside Proof High-Cut Bikini Bottoms

    This one hits before you even hit the water. These bikini bottoms feature a clean high V-cut accent for a trendy vibe made for sun-soaked plans. Pair with the matching top.

    Shop The Matching Top: Poolside Proof Hoop Detail Bandeau Bikini Top

    Fit & Features

    • Sleek knit-lined fabric
    • Bandeau halter-style neckline with ties
    • Removable padding
    • Hoop insert
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000023

    Category Name: Vacation Looks

    Price: $25.90

    Availability: In Stock

    Available Color: PINK

    Available Size: M, L

  • Hot Weather Favorite String Bikini Top

    Sun out, confidence on. These string bikini bottoms keep it clean and flattering with a barely there fit that feels effortless from shoreline walks to all-day lounging. 

    Shop The Matching Bikini Bottoms: Hot Weather Favorite Bikini Bottoms

    Fit & Features

    • Smooth swim fabric with a soft stretch feel
    • Halter triangle bust design
    • Removable padding for support and shaping
    • Adjustable string ties for a customizable fit
    • Hoop inserts
    • Runs true to size

    Style Number/Barcode: 07104-000016

    Category Name: Vacation Looks

    Price: $26.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hot Weather Favorite Bikini Bottoms

    Sun out, confidence on. These bikini bottoms keep it clean and flattering with a barely there fit that feels effortless from shoreline walks to all-day lounging. 

    Shop The Matching Bikini Top: Hot Weather Favorite String Bikini Top

    Fit & Features

    • Smooth swim fabric with a soft stretch feel
    • Hoop inserts
    • Minimal coverage
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000024

    Category Name: Vacation Looks

    Price: $25.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: M, L

  • Late Bloom Energy Floral Mesh Maxi Dress

    This is the kind of dress that makes the plan feel official. A floral mesh maxi dress with a sleek V-neck and open back moment that moves with you from drinks to dinner.

    Fit & Features

    • Lightweight floral mesh fabric with soft lining
    • V-neckline with spaghetti straps
    • Open back design
    • Body-skimming maxi dress silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001252

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L