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.

  • 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
  • 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
  • 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
  • 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
  • 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
    • 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
    • Better Together Bangle Bracelet Set

      The wrist stack practically styled itself. This bangle bracelet set features three resin bangles in varying silhouettes, making it the easiest way to add dimension and personality to any outfit.

      Fit & Features

      • Three-pack bangle bracelet set
      • Resin material
      • Varying silhouettes

      Style Number/Barcode: 07003-000259

      Category Name: Vacation Looks

      Price: $14.90

      Availability: In Stock

      Available Color: MULTI

      Available Size: NS

      Product Badge:
      • New Arrival
    • Aloha For Now Flower Hair Pin Set

      Say aloha to your new vacay-inspired look. These hibiscus flower hair pins add a playful tropical touch to ponytails, buns, and beach-day looks with a bloom for every mood.

      Fit & Features

      • Hibiscus flower designs
      • Metal clip closures
      • Three-pack set

      Style Number/Barcode: 07006-000159

      Category Name: Vacation Looks

      Price: $12.90

      Availability: In Stock

      Available Color: MULTI

      Available Size: NS

      Product Badge:
      • New Arrival
    • Low Key Luxe Tinted Sunglasses

      The kind of sunglasses that make even a simple outfit feel a little more polished. Featuring slim metal frames and warm brown-tinted lenses, this pair delivers a sleek, vintage-inspired finish.

      Fit & Features

      • Sleek round frames
      • Rubber nose supports
      • Tinted lenses
      • 100% UV protection

      Style Number/Barcode: 07008-000165

      Category Name: Vacation Looks

      Price: $12.90

      Availability: In Stock

      Available Color: BROWN

      Available Size: NS

      Product Badge:
      • New Arrival
    • Lei It On Me Flower Chain Belt

      The outfit was cute, then the flower chain belt showed up. Finished with sculpted hibiscus blooms, this statement belt brings vacation-ready charm to bottoms, swimsuits, and everything packed in between.

      Fit & Features

      • Hibiscus flower designs
      • Polished shine finish
      • Chain
      • Lobster clasp closure

      Style Number/Barcode: 07301-000397

      Category Name: Vacation Looks

      Price: $16.90

      Availability: In Stock

      Available Color: GOLD

      Available Size: NS

      Product Badge:
      • New Arrival
    • Destination Darling Floral Crop Top

      Vacation mode looks good on you. This floral halter top pairs a draped neckline with an open back silhouette for the kind of outfit perfect for every getaway plan.

      Fit & Features

      • Tropical floral print, stretchy knit fabric
      • Cowl halter neckline with tie straps
      • Open back
      • Fitted crop hem
      • Runs true to size

      Style Number/Barcode: 06001-000675

      Category Name: Vacation Looks

      Price: $26.90

      Availability: In Stock

      Available Color: MULTI

      Available Size: XS, S, M, L

      Product Badge:
      • New Arrival
    • Paradise Glow Tropical Sequin Beaded Mini Dress

      Vacation booked or not, this tropical sequin beaded mini dress is already packed for the plot. The stretchy lined mesh hugs close with a square neckline, strappy back cutout, and just enough shine to make every entrance feel intentional.

      Fit & Features

      • Tropical printed mesh fabric with knit lining, high stretch
      • Sequin and beaded swirl embroidered pattern
      • Sleeveless square neckline
      • Adjustable spaghetti straps
      • Lower back cutout
      • Mini-length bodycon silhouette
      • Runs true to size

      Style Number/Barcode: 05103-000878

      Category Name: Vacation Looks

      Price: $59.90

      Availability: In Stock

      Available Color: BLUE

      Available Size: XS, S, M, L

      Product Badge:
      • New Arrival
    • Meet Me In Maui Mesh Maxi Dress

      Covered in oversized tropical blooms and saturated sunset shades, this mesh midi dress brings vacation energy, whether you're headed to dinner by the water or a relaxing cruise.

      Fit & Features

      • Tropical print, lined mesh fabric with stretch
      • Strapless neckline
      • Bodycon silhouette
      • Fitted maxi-length hem
      • Runs true to size

      Style Number/Barcode: 05102-000763

      Category Name: Vacation Looks

      Price: $44.90

      Availability: In Stock

      Available Color: PINK

      Available Size: S, M, L

      Product Badge:
      • New Arrival
    • Ruffle Rush Tropical Floral Mini Dress

      Booked trip or just booking attention, this tropical floral ruffle mini dress gets the invite. The stretchy lined mesh, halter cowl neckline, open back, and flowy ruffled sash bring flirty movement with a fitted A-line shape.

      Fit & Features

      • Mesh fabric with knit lining, high stretch
      • Tropical floral print
      • Sleeveless cowl neckline
      • Tie-back halter straps, open back, lower tie-back spaghetti straps
      • Asymmetric tiered ruffled design, ruffled side sash accent
      • Mini-length hem, fitted A-line silhouette
      • Runs true to size

      Style Number/Barcode: 05102-000624

      Category Name: Vacation Looks

      Price: $49.90

      Availability: In Stock

      Available Color: MULTI

      Available Size: XS, S, M, L

      Product Badge:
      • New Arrival
    • Flirty Forecast Halter Ruffle Mini Dress

      Cue the entrance, this halter ruffle mini dress came ready to flirt. The high-stretch knit sculpts with ruching through the waist, a deep V-neckline, and tiered ruffles that bring movement without overthinking the outfit.

      Fit & Features

      • Sleek knit fabric, high stretch
      • Sleeveless deep V-neckline, beaded hardware accents
      • Tie-back halter straps, partially open back
      • Ruched detailing, drop waist
      • Tiered ruffled design, mini-length hem
      • A-line silhouette
      • Runs true to size

      Style Number/Barcode: 05103-001139

      Category Name: Vacation Looks

      Price: $42.90

      Availability: In Stock

      Available Color: PINK, TURQUOISE

      Available Size: XS, S, M, L

      Product Badge:
      • New Arrival
    • Wild Card Cowl Halter Mini Dress

      This dress doesn't do subtle, and that's exactly the point. The draped cowl neckline, daring open back, and mixed animal print make this halter mini dress the first thing you'll reach for when packing for vacation or nights out.

      Fit & Features

      • Mixed animal print, knit-lined fabric
      • Plunge cowl halter neckline, tie straps
      • Open tie back
      • Bodycon mini-length fit
      • Runs true to size

      Style Number/Barcode: 05103-001060

      Category Name: Vacation Looks

      Price: $39.90

      Availability: In Stock

      Available Color: GRAY

      Available Size: XS, S, M, L

      Product Badge:
      • New Arrival
    • Hailie Tropical Floral Lace Formal Dress

      Special Occasion

      Designed for the guest list that calls for something unforgettable, the Hailie dress brings together tropical lace, cascading ruffles, and a sculptural orchid accent for a look that feels equal parts romantic and statement-making. The plunging halter neckline, open back, and mermaid silhouette create striking movement from every angle.

      Fit & Features

      • Tropical floral print, lace fabric, smooth knit lining
      • Plunge ruffled halter neckline, tie straps
      • Front tropical flower pin
      • Open tie-back, lower zipper and hook-eye closure
      • Cascading ruffle trim
      • Mermaid floor-length silhouette
      • Runs true to size

       

      Where to Wear:

      Destination weddings, vacations, honeymoons, resorts, cruises, engagement parties, cocktail events, birthday dinners, date nights, summer galas, yacht parties

      Style Number/Barcode: 05002-001583

      Category Name: Vacation Looks

      Price: $79.90

      Availability: In Stock

      Available Color: PINK

      Available Size: XS, S, M, L

      Product Badge:
      • Ships Free
    • Seaside Stunner Halter Maxi Dress

      The kind of dress that makes an entrance. With a textured finish, beaded cutout details, and a sleek halter neckline, this maxi dress is perfect for vacations, bridal celebrations, and brunch dates.

      Fit & Features

      • Sweater knit fabric, knit lining
      • Halter neckline, tie straps
      • Cutout bust with beaded accents
      • Center back slit
      • Bodycon maxi silhouette
      • Runs true to size

      Style Number/Barcode: 06005-000326

      Category Name: Vacation Looks

      Price: $44.90

      Availability: In Stock

      Available Color: WHITE

      Available Size: XS, S, M, L

      Product Badge:
      • New Arrival
    • Beach Treasures Earrings Pack

      This 20-piece earring set is packed with beach-inspired details, from shells and starfish to palms and pearls, making it the perfect mix-and-match collection for vacations, weekend plans, and everyday styling.

      Fit & Features

      • 20-piece earring set
      • Various styles and beach-inspired designs
      • Faux pearls and rhinestone embellishments
      • Polished metal finish
      • Post-back and omega closures

       

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

      Style Number/Barcode: 07001-000416

      Category Name: Vacation Looks

      Price: $14.90

      Availability: In Stock

      Available Color: GOLD

      Available Size: NS

      Product Badge:
      • New Arrival
    • Catch The Vibe Beaded Halter Top

      The outfit did not come to play, and neither did this top. Featuring beaded string detailing, a halter neckline, and an open back design, this crop top brings the sass to denim shorts and sandals.

      Fit & Features

      • Knit fabric
      • Square halter neckline, tie straps
      • Open tie-back
      • Beaded front design
      • Crop-length hem
      • Runs true to size

      Style Number/Barcode: 06001-000523

      Category Name: Vacation Looks

      Price: $39.90

      Availability: In Stock

      Available Color: BROWN

      Available Size: XS, S, M, L

      Product Badge:
      • New Arrival
    • Snap Ready Rectangle Phone Grip

      Your phone just got a better grip on the situation. This rectangle phone grip keeps scrolling, selfies, and content checks feeling way more secure without adding bulk.

      Fit & Features

      • Flexible rubber material
      • Rectangle shape
      • Raised suction cup design

      Style Number/Barcode: 07308-000106

      Category Name: Vacation Looks

      Price: $6.90

      Availability: In Stock

      Available Color: CLEAR, BLACK, PINK

      Available Size: NS

      Product Badge:
      • New Arrival
    • Georgina Glitter Cutout Formal Dress

      Special Occasion

      The Georgina formal dress blends shimmering glitter knit fabric with a sleek, form-hugging long silhouette. A sleeveless halter sweetheart neckline with hardware stone and ball inserts, side cutout bodice, hoop detail, and high side slit create a look that feels equal parts polished and unforgettable.

      Fit & Features

      • Glitter knit fabric, smooth knit lining, high stretch
      • Halter neckline, padded bra cups, hardware stone and ball inset
      • Adjustable spaghetti straps
      • Side bodice cutout, hoop waist insert
      • High side slit
      • Form-hugging long-length silhouette
      • Runs true to size

       

      Where to Wear:

      Destination weddings, cocktail celebrations, birthday dinners, vacations, honeymoons, resort getaways, date nights, luxury cruises, yacht parties

      Style Number/Barcode: 05002-001423

      Category Name: Vacation Looks

      Price: $69.90

      Availability: In Stock

      Available Color: BROWN

      Available Size: XS, S, M, L

      Product Badge:
      • New Arrival
    • After Hours Bloom Floral Maxi Dress

      Sleek, sculpted, and made to linger in the memory. This mesh maxi dress features a square neckline and a curve-hugging fit that feels elevated enough for dressy occasions and vacay.

      Fit & Features

      • Stretch mesh fabrication with smooth lining, floral print
      • Spaghetti straps with a square neckline
      • Fitted bodice through the hips
      • Curve-hugging fit, flared maxi hem
      • Runs true to size

      Style Number/Barcode: 05101-000721

      Category Name: Vacation Looks

      Price: $49.90

      Availability: In Stock

      Available Color: BLACK

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

      Product Badge:
      • New Arrival
    • Vivid Escape Ruffle Halter Mini Dress

      A bold mix of prints and flowing movement makes this one impossible to overlook. This printed mini dress features a halter neckline, plunging front, and layered ruffle hem that creates dimension with every step. Perfect for vacations, day parties, and warm-weather plans that deserve something a little more memorable.

      Fit & Features

      • Lined mesh fabric
      • Halter neckline with plunging front detail
      • Mixed floral and animal print design
      • Form-hugging fit
      • Layered ruffle mini hem with cascading side ruffle
      • Runs true to size

      Style Number/Barcode: 05103-000937

      Category Name: Vacation Looks

      Price: $46.90

      Availability: In Stock

      Available Color: PINK

      Available Size: XS, S, M, L

      Product Badge:
      • New Arrival