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.

  • Vacay RSVP Tropical Flower Statement Earrings

    Serving vacation RSVP energy. These tropical flower statement earrings bring the fun to strapless dresses, beach dinners, and every outfit that needs one extra thing to feel fully styled.

    Fit & Features

    • Acrylic material
    • Statement tropical flower design
    • Post-back closure

     

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

    Style Number/Barcode: 07001-000346

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: PINK

    Available Size: NS

  • Island On The Mind Tropical Tank Top

    This top feels like booking the trip. The halter neckline and oversized floral print bring instant vacation vibes, whether you’re headed beachside or just dressing like it.

    Fit & Features

    • Knit stretchy fabric
    • Tropical floral print
    • Halter neckline, tie straps
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-000628

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: TEAL

    Available Size: XS, S, M, L

  • Just Enough Drama Hammered Drop Earrings

    These hammered drop earrings bring that bold, sculptural vibe to dinner reservations, rooftop cocktails, and every last-minute “wait, I’m coming too” text.

    Fit & Features

    • Drop silhouette
    • Hammered metal design
    • Post-back closure

     

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

    Style Number/Barcode: 07001-000354

    Category Name: Vacation Looks

    Price: $9.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Luxe Vacay Statement Rhinestone Leaf Stud Earrings

    Vacation state of mind, but make it sparkly. These statement rhinestone leaf stud earrings bring just enough drama to dress up bikinis, oversized button-downs, or that last-minute dinner look.

    Fit & Features

    • Large leaf stud design
    • Mini rhinestone embellishments
    • Post-back closure

     

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

    Style Number/Barcode: 07001-000348

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Sultry Tease Open Back Top

    This top was basically made for parties, dancing, and taking “just one pic” that turns into fifty. The draped halter neckline and chunky ring details bring the perfect mix of sultry and effortless to your look.

    Fit & Features

    • Slinky knit fabric
    • Cowl halter neckline, hoop ring inserts
    • Open tie back design
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000661

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: TEAL

    Available Size: XS, S, M, L

  • Vacay Vibe Leaf Bobby Pin Set

    Caught the vacay vibe before the outfit even loaded. This leaf bobby pin set adds a little extra something to buns, braids, and last-minute hair days that still deserve compliments.

    Fit & Features

    • Four-pack bobby pin set
    • Metal pins
    • Resin and metal leaf-shaped designs

    Style Number/Barcode: 07006-000133

    Category Name: Vacation Looks

    Price: $8.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Cabana Crush Chevron Bikini Top

    Booked the cabana before you even finished packing. This bikini top brings major resort mood with its retro-inspired chevron print, hoop inserts, and matching pieces that was made for poolside photos.

    Shop The Matching Bottoms: Cabana Crush Chevron Bikini Bottoms
    Shop The Matching Sarang: Cabana Crush Chevron Sarong Wrap

    Fit & Features

    • Chevron print, sleek knit-lined fabric
    • Hoop insert halter neckline
    • Adjustable back ties
    • Padded bra cup inserts
    • Runs true to size

    Style Number/Barcode: 07104-000033

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: S, M, L

  • Cabana Crush Chevron Sarong Wrap

    Booked the cabana before you even finished packing. This sarang wrap bring major resort mood with its retro-inspired chevron print, tie-waist design, and matching pieces that was made for poolside photos.

    Shop The Matching Top: Cabana Crush Chevron Bikini Top
    Shop The Matching Bottoms: Cabana Crush Chevron Bikini Bottoms

    Fit & Features

    • Chevron print, sleek knit fabric
    • Tie-waist design
    • Wrap styling
    • Runs true to size 

    Style Number/Barcode: 07105-000048

    Category Name: Vacation Looks

    Price: $25.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: NS

  • Cabana Crush Chevron Bikini Bottoms

    Booked the cabana before you even finished packing. These bikini bottoms bring major resort mood with its retro-inspired chevron print, hoop inserts, and matching pieces that was made for poolside photos.

    Shop The Matching Top: Cabana Crush Chevron Bikini Top
    Shop The Matching Sarang: Cabana Crush Chevron Sarong Wrap

    Fit & Features

    • Chevron print, sleek knit-lined fabric
    • Hoop insert waist detail
    • Cheeky cut
    • Runs true to size 
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000047

    Category Name: Vacation Looks

    Price: $25.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: S, M, L

  • Chic Invite Metallic Rope Box Clutch

    Tiny bag, huge social calendar. This metallic rope box clutch brings the chic finishing touch your looks have been waiting for, whether you’re headed to cocktails, weddings, or dressing like the RSVP said “best dressed only.”

    Fit & Features

    • Oval-shaped design
    • Metallic woven rope exterior
    • Top metal clasp closure, metal trim
    • Woven interior lining
    • Attachable chain-link shoulder strap

    Style Number/Barcode: 07203-000184

    Category Name: Vacation Looks

    Price: $30.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Pretty Extra Flower Statement Stud Earrings

    Pretty extra in the best way. These flower statement stud earrings were made for rooftop dinners, spontaneous selfies, and making a simple outfit look way more intentional.

    Fit & Features

    • Metal stud earrings
    • Large filigree flower design with layered petals
    • Post-back closures

     

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

    Style Number/Barcode: 07001-000430

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Perfect Flirt Ruffle Sleeve Tie-Front Top

    The kind of top that suddenly has your group chat asking for the link. This ruffle sleeve tie-front top features a flattering fitted silhouette with a cropped hem that pairs perfectly with the matching mini skort.

    Shop Matching Bottoms: Perfect Flirt Ruffle Mini Skort

    Fit & Features

    • Sleek knit fabric, high stretch
    • V-neckline, tie-front design
    • Short ruffle sleeves
    • Cropped hem
    • Fitted silhouette
    • Runs true to size

    Style Number/Barcode: 06202-000115

    Category Name: Vacation Looks

    Price: $22.90

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Diamond District Arm Cuff

    Minimal outfit, dramatic accessories, problem solved. This sleek arm cuff wraps around with sculptural shine and rhinestone details that catch the light from every angle.

    Fit & Features

    • Textured polished finish
    • Open wrap silhouette
    • Rhinestone accents
    • Sculptural design

    Style Number/Barcode: 07003-000232

    Category Name: Vacation Looks

    Price: $13.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

    Product Badge:
    • Best Seller
  • Trendy Style Resin Bangle Bracelet Set

    Serving stacked wrist moments with zero effort required. This resin bangle bracelet set adds the perfect pop to tanks, oversized button-downs, and every last-minute outfit that somehow still looks planned.

    Fit & Features

    • Two-pack bangle bracelet set
    • Resin material
    • Smoothy, glossy finish
    • Wide designs

    Style Number/Barcode: 07003-000308

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: NS

  • Stacked And Booked Bangle Bracelet Set

    Your outfit called and said it needed these. This bangle bracelet set mixes resin textures, sleek metal details, and mini rhinestone accents for the kind of stack that makes even a basic tee feel planned.

    Fit & Features

    • Five-pack bangle bracelet set
    • Two resin bangles
    • Three metal bangles
    • Assorted silhouettes and designs
    • Mini rhinestone embellishments

    Style Number/Barcode: 07003-000307

    Category Name: Vacation Looks

    Price: $15.90

    Availability: In Stock

    Available Color: GREEN

    Available Size: NS

  • Extra Chic Pearl Charm Bracelet

    A little extra in the best way possible. This pearl charm bracelet brings the layered look without the styling stress, thanks to the chunky chain and mixed charms that make every outfit feel way more chic.

    Fit & Features

    • Chunky chain
    • Beaded, faux pearl, and circular textured charms with mini rhinestones
    • Lobster clasp closure with extender

    Style Number/Barcode: 07003-000309

    Category Name: Vacation Looks

    Price: $11.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Artsy Edge Flower Statement Cuff

    This flower statement cuff understood the assignment the second you put it on. The sculpted design and textured metal finish bring an artsy edge that makes even a basic outfit feel styled.

    Fit & Features

    • Thin textured metal silhouette
    • Flower sculpted statement design
    • Hinge closure

    Style Number/Barcode: 07003-000310

    Category Name: Vacation Looks

    Price: $14.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Extra Attention Slinky Knit Cutout Maxi Dress

    The kind of dress that changes the whole mood the second you walk in. This slinky knit maxi dress hugs in all the right places with daring cutouts, gleaming hardware accents, and a plunging halter neckline made for plans that deserve a little extra attention.

    Fit & Features

    • Slinky knit fabric, high stretch
    • Sleeveless plunging V-neckline
    • Dual waist cutouts, hardware accents
    • Tie-back halter straps
    • Partially open back, lower zipper closure
    • Maxi-length hem, bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001205

    Category Name: Vacation Looks

    Price: $54.90

    Availability: In Stock

    Available Color: BLACK

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

  • Off Duty Cutie Foldover Knit Shorts

    The shorts you'll love for off-duty days. Designed with a soft textured knit and foldover waistband, these ultra-comfy knit shorts are giving beach mornings, coffee runs, and cute looks all weekend.

    Fit & Features

    • Soft texture knit fabric with stretch
    • Foldover waistband
    • Form-hugging fit
    • Cheeky hem
    • Runs true to size

    Style Number/Barcode: 06503-000272

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Bethany Tropical Bead A-Line Mini Dress

    Special Occasion

    The Bethany mini dress was made for sunny destinations. This beaded mesh mini dress features a tropical pattern, an open back, and a flattering A-line silhouette that brings just the right amount of getaway glamour.

    Fit & Features

    • Tropical beaded pattern, mesh fabric, smooth lining
    • Square neckline
    • Spaghetti straps
    • Cutout back detail
    • A-line mini-length silhouette
    • Runs true to size

    Where to Wear:

    Vacations, honeymoons, birthday dinners, getaways, date nights, parties

    Style Number/Barcode: 05001-000656

    Category Name: Vacation Looks

    Price: $89.90

    Availability: In Stock

    Available Color: CORAL

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

    Product Badge:
    • Ships Free
  • Flirty Chic Cutout Maxi Dress

    The kind of dress that makes every plan feel a little more chic. With its flowy silhouette, flirty cutout detail, and side pockets, this maxi dress was made for vacations, weekend plans, and showers.

    Fit & Features

    • Gauze cotton woven fabric, woven lining
    • Sweetheart neckline, spaghetti straps
    • Open tie-back design
    • Cutout bodice
    • Hidden side pockets
    • Flowy maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000559

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Vacation Flirt Knit Cutout Maxi Dress

    Serving vacation flirt and trendy vibes. This knit maxi dress hugs in all the right places with lace-up cutouts, a plunging halter neckline, and an open back that knows exactly what it’s doing.

    Fit & Features

    • Knit fabric with flame stitch pattern
    • Sleeveless plunging V-neckline, beaded strap
    • Tie-back halter straps
    • Lace-up side cutouts
    • Open back, lower tie-back spaghetti straps
    • Maxi-length bodycon silhouette, back slit accent
    • Runs true to size

    Style Number/Barcode: 05102-000606

    Category Name: Vacation Looks

    Price: $48.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

  • On Your Mind Abstract Print Mesh Mini Dress

    This mini dress doesn’t wait for compliments. The abstract print, plunging halter neckline, and ruched mesh fit were made for making an entrance and staying on everyone’s mind.

    Fit & Features

    • Mesh fabric with knit lining, high stretch
    • Abstract print
    • Sleeveless plunging scoop neckline
    • Tie-back halter straps, open back
    • Ruched wrap-front design, hardware accent, center sash
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000641

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Sunkissed Stunner Halter Maxi Dress

    Vacation mode called, and this maxi dress already answered. With a plunging halter neckline, bold cutout details, and a flowy front slit silhouette, this maxi dress was made for beachside brunches, sunny getaways, and weekend plans.

    Fit & Features

    • Artsy print, woven fabric
    • Halter neckline
    • Strappy cutout bodice, back zipper and hook-eye closure
    • High front slit
    • Flowy maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000645

    Category Name: Vacation Looks

    Price: $59.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: XS, S, M, L