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.

  • Simply Elevated Cork Wedges

    Simply elevated is the vibe. These cork wedges pair a knotted woven toe strap with slim adjustable ankle straps and the luxe fit cushioned insole for polished height that moves from brunch to rooftop plans with ease.

    Fit & Features

    • Cork wedge heel
    • Open almond-shaped toe
    • Woven toe strap with knot design
    • Thin adjustable ankle straps, buckle closure
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07406-000037

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

    Product Badge:
    • New Arrival
  • Rare Find Animal Print Maxi Dress

    A little wild, a little glamorous, and impossible to scroll past. This animal print mesh maxi dress pairs a sweetheart neckline, cutout details, hardware accents, and a dramatic front sash for the kind of entrance people remember.

    Fit & Features

    • Multi-animal print, lined mesh fabric
    • Strapless sweetheart neckline
    • Hardware bust insert with cascading sash
    • Cutout bodice
    • Curve-hugging, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000803

    Category Name: Vacation Looks

    Price: $54.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Catherine Crochet Cutout Formal Dress

    Special Occasion

    Sunset plans, destination energy, and a dress that knows exactly how to make an entrance. This crochet mermaid gown brings the drama with a plunging halter neckline, waist cutouts, beaded accents, and fringe trim made to move with you.

    Fit & Features

    • Crochet knit fabric
    • Plunging halter neckline
    • Waist cutout design
    • Beaded tie front accents
    • Mermaid silhouette
    • Floor-length hem
    • Runs true to size

     

    Where to Wear:

    Destination weddings, honeymoons, resort getaways, vacations, cruises, yacht parties, sunset cocktail events, date nights, birthday dinners

    Style Number/Barcode: 05002-001605

    Category Name: Vacation Looks

    Price: $99.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunset Spritz Multi-Print Ruffle Mini Skort

    Pool plans, brunch plans, “wait where are we going next?” plans. This multi-print ruffle mini skort brings the flirty vibe with a flouncy hem, low-rise fit, and hidden shorts.

    Fit & Features

    • Knit fabric, high stretch
    • Floral and animal multi-print pattern
    • Low-rise waist, ruched detailing
    • Side ruffled accents
    • Tiered ruffled mini-length hem, A-line fit
    • Hidden built-in shorts
    • Runs true to size

    Style Number/Barcode: 06503-000327

    Category Name: Vacation Looks

    Price: $34.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Jailene Cutout Coin Charm Formal Dress

    Special Occasion

    Designed for the girl who never blends into the background, the Jailene formal dress is all about movement, shimmer, and statement-making confidence. Crafted from sleek slinky fabric, this halter mermaid gown features dramatic cutouts, a thigh-high slit, and cascading coin embellishments that catch the light with every step, dance, and slow-motion entrance.

    Fit & Features

    • Slinky knit stretchy fabric
    • Halter neckline, tie straps
    • Partial open
    • Cutout bodice with coin charm trimmed straps
    • High side slit
    • Mermaid floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Vacations, honeymoons, resort getaways, destination celebrations, birthday dinners, yacht parties

    Style Number/Barcode: 05002-001779

    Category Name: Vacation Looks

    Price: $79.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Ships Free
  • Floral Mood Mesh Lace-Up Tube Top

    Florals with a little edge. This mesh lace-up tube top brings a sleek strapless fit, lined stretch feel, and tie-back detail made for plans that need a stronger outfit. Style with the matching maxi skirt.

    Shop Matching Bottoms: Floral Mood Mesh Maxi Skirt

    Fit & Features

    • Mesh fabric with knit lining, high stretch
    • Large floral print
    • Strapless straight-across neckline
    • Lace-up back design, tie closure
    • Mid-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06001-000520

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Statement Maker Shield Sunglasses

    Serving expensive taste with minimal effort. These shield metal sunglasses bring instant attitude to any look, whether you're heading on vacation, running errands, or making the sidewalk your runway.

    Fit & Features

    • Shield silhouette
    • Clear tinted lenses
    • 100% UV protection
    • Rubber nose supports
    • Metal arms with plastic trim

    Style Number/Barcode: 07008-000183

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: NS

    Product Badge:
    • New Arrival
  • Treasure Found Coin Charm Earrings

    A little shimmer, a little movement. These teardrop hoop earrings feature a colored teardrop gem and cascading coin charm fringe that brings a boho-inspired allure to any look.

    Fit & Features

    • Sleek teardrop shaped hoop
    • Colored gemstone charm
    • Cascading mini coin charm fringe
    • Fish hook with rubber stoppers

     

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

    Style Number/Barcode: 07001-000403

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

    Product Badge:
    • New Arrival
  • Sun Chaser Beaded Crochet Mini Dress

    Vacation bag called. This beaded crochet mini dress is first on the list. The bodycon fit, halter neckline, and chic beaded details bring just enough drama for dinner plans, rooftop drinks, and every photo op.

    Fit & Features

    • Crochet knit fabric, moderate stretch
    • Sleeveless V-neckline, beaded trim under the bust
    • Halter strap
    • Open back
    • Mini-length hem, beaded fringe trim
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000375

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Paradise Crush Halter Skater Dress

    Serving vacation plans from every angle. This flirty mesh skater dress pairs a plunging halter neckline with an open tie-back and layered ruffle skirt for a look that's made for getaways, birthday dinners, and golden hour photos.

    Fit & Features

    • Multi-print lined mesh fabric, tulle trim lining
    • Plunge halter neckline, tie straps
    • Open dual tie back straps
    • Fitted bodice
    • Tiered ruffle mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000983

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Floral Mood Mesh Maxi Skirt

    Florals with a little edge. This mesh lace-up maxi skirt brings a sleek bodycon fit, lined stretch feel, and back slit detail made for plans that need a stronger outfit. Style with the matching tube top.

    Shop Matching Top: Floral Mood Mesh Lace-Up Tube Top

    Fit & Features

    • Mesh fabric with full-length knit lining, high stretch
    • Large floral print
    • High-rise waist
    • Back slit accent
    • Maxi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06501-000133

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Polished Halter Bodycon Maxi Dress

    A smooth, shine-kissed finish makes this one feel instantly dressed up. The curve-hugging shape, plunging neckline, and waist cutouts bring the drama for vacation dinners, cocktail parties, and every RSVP that needs a little extra.

    Fit & Features

    • Slinky knit fabric with stretch
    • Halter neckline with plunging V front
    • O-ring hardware at center waist
    • Side and underbust cutout details
    • Body-hugging maxi fit
    • Runs true to size

    Style Number/Barcode: 05102-000825

    Category Name: Vacation Looks

    Price: $46.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Hardware Cutout Halter Maxi Dress

    Consider this your shortcut to a sharper going-out look. Metallic ring accents and angled front openings give this body-skimming dress a sculpted finish made for dressy occasions.

    Fit & Features

    • Lined smooth stretch knit fabric
    • Halter tie neckline
    • Front cutouts with metal hardware accents
    • Body-skimming fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000807

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • All Eyes Here Crochet Mini Dress

    This is the dress that gets the double-take. With a sculpting crochet-knit texture, side cutouts, and a lace-up back that steals the show, it's made for cocktails, birthday plans, and vacations.

    Fit & Features

    • Crochet fabric
    • Strapless neckline
    • Cutout design
    • Lace-up back detail
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000398

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Caught Daydreaming Butterfly Lace Top

    Designed with intricate butterfly lace, subtle sequin details, and an open tie-back silhouette, this halter top is romantic and unforgettable. Pair it with your favorite bottoms and sandals.

    Fit & Features

    • Butterfly sequin-embellished fabric
    • Halter V-neckline, tie straps
    • Open tie-back detail
    • Sheer fitted hem
    • Runs true to size

    Style Number/Barcode: 06003-000384

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: BROWN, TEAL

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Sweet Bloom Flower Earrings

    The kind of earrings that do all the talking. Featuring dimensional flower petals with a luminous pearl center, these statement earrings bring a romantic finish to wedding guest looks, cocktail soirees, and every outfit that deserves a statement.

    Fit & Features

    • Dimensional flower shape design
    • Faux pearl center accent
    • Post-back closure 

     

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

    Style Number/Barcode: 07001-000433

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: PEARL

    Available Size: NS

    Product Badge:
    • New Arrival
  • Blooming With Plans Flower Earrings

    These cascading flower earrings bring a playful touch of shine and movement that's ready for weddings, showers, and every RSVP on your calendar.

    Fit & Features

    • Polished metal finish
    • Cascading flower design
    • Sleek linear silhouette
    • Fish hook with rubber stopper

     

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

    Style Number/Barcode: 07001-000409

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

    Product Badge:
    • New Arrival
  • Art Of Accessorizing Statement Necklace

    The kind of necklace that makes a simple outfit look styled. With its oversized pendant and mixed-material design, this statement necklace is perfect for vacations, weekend plans, and summer date nights!

    Fit & Features

    • Layered chain design
    • Statement stone pendant
    • Statement mixed metal and wood accent pendant
    • Lobster clasp closure

    Style Number/Barcode: 07002-000487

    Category Name: Vacation Looks

    Price: $16.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

    Product Badge:
    • New Arrival
  • Artsy Trio Hoop Earrings

    These hoop earrings bring instant dimension with a layered look that makes even the simplest outfit feel thoughtfully styled.

    Fit & Features

    • Hammered texture design
    • Cascading hoop silhouettes
    • Post-back closure

     

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

    Style Number/Barcode: 07001-000389

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: SILVER

    Available Size: NS

    Product Badge:
    • New Arrival
  • Delicate Details Stone Belly Chain

    Delicate chains and colorful stone accents give this dainty belly chain a collected-on-vacation feel that's perfect for bikinis, low-rise bottoms, and every bare midriff look.

    Fit & Features

    • Colored stone embellishments
    • Dainty chain design
    • Polished finish
    • Lobster clasp closure

    Style Number/Barcode: 07002-000490

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: PINK

    Available Size: NS

    Product Badge:
    • New Arrival