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.

  • Layered Luxe Bracelet Five-Pack

    Stacked and styled in seconds. This five-pack bangle bracelet mixes sleek metal bands with a bold hinge bangle for that effortless layered look, no overthinking required.

    Fit & Features

    • Five-pack bangle bracelet set
    • Various styles and designs
    • Hinge closure and slip-on styles

    Style Number/Barcode: 07003-000196

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Petals On Repeat Floral Earrings

    Soft glam, but make it playful. These floral drop earrings bring a flirty, feminine touch with cascading blooms that instantly dress up your brunch fits and date-night looks.

    Fit & Features

    • Linear drop silhouette
    • Triple floral design
    • Textured center detail
    • Post back closure

     

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

    Style Number/Barcode: 07001-000272

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All The Angles Textured Hoop Earrings

    Minimal effort, maximum polish. These textured hoop earrings add just enough shine and detail to make your everyday fit feel styled in seconds.

    Fit & Features

    • Polished construction
    • Medium hoop silhouette
    • Textured etched front detail
    • Post back closure

     

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

    Style Number/Barcode: 07001-000332

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Breezy Off-Shoulder Poncho Top

    That effortless throw-on and go layer. This crop poncho top drapes off the shoulder with a relaxed fit that pairs perfectly with denim, boots, and stacked jewelry for an easy, cute vibe.

    Fit & Features

    • Texture knit fabric
    • Off-shoulder neckline
    • Relaxed cropped silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000311

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: BROWN, IVORY, WINE

    Available Size: XS/S, M/L

    Product Badge:
    • Back In Stock
  • Island After Hours One Shoulder Maxi Dress

    This is what you pack when the itinerary says “sunset drinks,” and you plan on being the view. The one-shoulder neckline with hardware detail gives elevates the look, while the tropical floral print and front slit keep it flowy, flirty, and very camera-ready.

    Fit & Features

    • Tropical floral print knit fabric
    • One-shoulder neckline
    • Statement hardware strap detail
    • Front slit with ruffle accent
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 05102-000419

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Flirt Polka Dot Mesh Mini Skort

    Okay, but this skort just RSVP’d yes for you. This polka dot mesh mini skort drapes perfectly with a tiered ruffled design and flirty A-line fit, making it your go-to for party plans, birthday dinners, or that last-minute invite that has you walking in like you planned it all week.

    Shop Matching Top: Such A Flirt Polka Dot Mesh Cowl Neck Top

    Fit & Features

    • Polka dot mesh fabric, high stretch
    • Mid-rise waist with ruching
    • Tiered ruffled design
    • Mini-length overlay, A-line silhouette
    • Hidden fitted knit shorts
    • Runs true to size

    Style Number/Barcode: 06503-000245

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK/WHITE

    Available Size: L

    Product Badge:
    • Sale
  • Kim Rhinestone Leopard Mermaid Formal Dress

    Special Occasion

    Designed to command attention the moment you arrive, the Kim rhinestone leopard gown brings bold glamour to any formal setting. The mermaid floor-length silhouette is finished with a striking cutout back that feels confident, sculpted, and unforgettable.

    Fit & Features

    • Rhinestone embellished mesh-lined fabric, leopard pattern
    • Plunge V-neckline, wide shoulder straps
    • Side zipper and hook-eye closure
    • Cutout back detail
    • Mermaid floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Prom, black-tie galas, weddings, red-carpet occasions, formal birthday celebrations, upscale receptions, fancy art gallery openings, award show dinners, special date nights

    Style Number/Barcode: 05002-001039

    Category Name: Vacation Looks

    Price: $159.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bare Minimum Drama Sequin Crochet Fringe Poncho

    Sheer, shimmery, and not here to blend in. This sequin crochet fringe poncho is the ultimate layer when your bikini top or bralette deserves a little extra attention, but you still want that effortless, thrown on and thriving vibe.

    Fit & Features

    • Lightweight sheer crochet fabric
    • Sequin embellishments
    • Relaxed poncho silhouette
    • Open neckline with easy slip-on design
    • Fringe hem
    • Runs true to size

    Style Number/Barcode: 06005-000288

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dripping In Drama Hammered Lariat Necklace

    Serving poolside goddess with zero effort. This hammered lariat necklace drops low with bold statement shine, instantly elevating plunging necklines, swim looks, or that pic-worthy dress you’ve been saving.

    Fit & Features

    • Metal construction with hammered texture
    • Long lariat silhouette
    • Oversized shaped pendants

    Style Number/Barcode: 07002-000371

    Category Name: Vacation Looks

    Price: $19.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beachside Siren Mesh Swim Cover Up

    Beach walk, but make it cinematic. This mesh cinched cover up hugs in all the right places with adjustable side ties and a dramatic slit, perfect for layering over your bikini when you want a little mystery with your moment.

    Fit & Features

    • Lightweight sheer mesh fabric
    • Fitted maxi cover-up silhouette
    • Mid-rise waist
    • High side slit 
    • Ruched accents
    • Runs true to size

    Style Number/Barcode: 07105-000038

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: L/XL

    Product Badge:
    • Sale
  • Sun Chaser Studded Bandeau Bikini Top

    Sun out, standards high. This bandeau bikini top keeps it sleek with a halter strap detail and subtle stud trim, giving you that sculpted, secure fit whether you’re beach lounging or chasing the next swim pic.

    Shop Matching Bottoms: Sun Chaser Studded Bikini Bottoms

    Fit & Features

    • Smooth stretch fabrication
    • Bandeau bikini top silhouette
    • Halter neck strap for added support
    • Studded trim
    • Runs true to size

    Style Number/Barcode: 07104-000019

    Category Name: Vacation Looks

    Price: $10.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Whimsical Charm Butterfly Claw Clip Set

    Your five-minute hair routine just got a glow up. This four-piece butterfly claw clip set adds a dreamy, throwback touch to messy buns, half-up styles, and everything in between—cute, effortless, and always camera ready.

    Fit & Features

    • Four-piece hair claw clip set
    • Butterfly designs
    • Claw clip closure

    Style Number/Barcode: 07006-000119

    Category Name: Vacation Looks

    Price: $3.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bloom Agenda Floral Mesh Halter Maxi Dress

    RSVP secured and outfit handled. This floral mesh halter maxi dress sculpts with high-stretch comfort, features a statement flower hardware accent, and serves a partially open back that’s perfect for photo ops.

    Fit & Features

    • Sheer mesh fabric with full-length knit lining, high stretch
    • Large floral print
    • Sleeveless halter neckline, tie-back design
    • Metal flower hardware accent
    • Partially open back
    • Maxi-length form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000881

    Category Name: Vacation Looks

    Price: $54.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Compliment Me Lace Ruffle A-Line Mini Dress

    This lace ruffle A-line mini dress hugs through the sweetheart bodice, shows just enough with waist cutouts, and flares into a floaty silhouette that moves when you do—perfect for parties, bridal events, or any time you want compliments on repeat.

    Fit & Features

    • Sheer lace fabric with lining
    • Sleeveless sweetheart neckline
    • Tie-back halter straps, partially open back
    • Asymmetric waist cutouts leading to open lower back
    • Ruffled trim
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000867

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Soft Glam Agenda Lace Ruffle Skater Dress

    Soft glam just secured your weekend plans. This lace skater dress hugs at the waist, flares into flirty ruffles, and is basically made for date night, birthday dinners, and any invite that says “dress cute.”

    Fit & Features

    • Lace fabric with lining
    • Sleeveless deep V-neckline
    • Halter tie-back straps
    • Open back
    • Tiered ruffled design
    • Short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001100

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • DIME Retro Slim Sunglasses

    Serving vintage energy with a modern edge. These DIME slim rectangular sunglasses feature a rich mocha hue frame with tinted lenses that instantly elevate any look—from coffee runs to coastlines.

    Fit & Features

    • Slim rectangular frame
    • Tinted lenses
    • 100% UV protection
    • Lightweight feel
    • "Dime" logo on the arms

    Style Number/Barcode: 07008-000144

    Category Name: Vacation Looks

    Price: $14.97 $30.00

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • DIME Glendale Shield Sunglasses

    If the invite calls for sunny day fun, these are coming with you. These DIME oversized shield sunglasses bring bold energy with a mirrored lens and sleek arms that instantly level up any look.

    Fit & Features

    • Lightweight frames
    • Oversized shield silhouette
    • Mirrored tinted lens
    • 100% UV protection
    • Slim arms with "Dime" logo

    Style Number/Barcode: 07008-000140

    Category Name: Vacation Looks

    Price: $14.97 $30.00

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • DIME Cat Eye Sunglasses

    Minimal effort, maximum attitude. These DIME sleek cat eye sunglasses feature a sharp silhouette and polarized tinted lenses that instantly elevate leather jackets, slick buns, and last-minute dinner plans.

    Fit & Features

    • Glossy acetate frame
    • Narrow cat eye silhouette
    • Polarized tinted lenses with 100% UV protection
    • Slim arms with "Dime" logo

    Style Number/Barcode: 07008-000139

    Category Name: Vacation Looks

    Price: $14.97 $30.00

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • DIFF Aspyn Ovard Tortoise Sunglasses

    POV: you just found the sunglasses that pull the whole outfit together. These DIFF oval sunglasses add instant cool to your everyday looks, whether you’re headed to brunch, campus, or a last-minute photo dump moment.

    Fit & Features

    • Smooth acetate material
    • Structured oval sunglasses silhouette
    • Tinted lenses with 100% UV protection
    • Slim curved arms with "Diff" logo

    Style Number/Barcode: 07008-000142

    Category Name: Vacation Looks

    Price: $98.00

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweetly Calculated Lace Trim Mini Dress

    A little romance, a little edge. This halter mini dress hugs through the bodice, flares into an easy A-line shape, and finishes with lace trim that makes it feel styled even before you add heels.

    Fit & Features

    • Mesh-lined fabric, lace trim
    • Halter neckline
    • Partial open back
    • Bodycon A-line mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000828

    Category Name: Vacation Looks

    Price: $44.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Golden Glow Strapless Maxi Dress

    Serving sunkissed confidence with every step. The strapless lace maxi dress contours through the bodice, highlights the neckline with hardware detail, and falls into a sleek, elongating shape that feels equal parts elevated and effortless.

    Fit & Features 

    • Striped design, lace-lined fabric
    • Strapless sweetheart neckline, hardware insert, non-slip grip lining
    • Form-hugging
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000425

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Confidence Halter Crop Top

    It’s the kind of top that makes sunset cocktails turn into dinners with a view. The floral cowl halter crop top features a fluid drape, statement orchid accent, and tie-back halter neckline that feels flirty, elevated, and ready for warm nights out.

    Shop The Matching Skirt: Floral Confidence Maxi Skirt

    Fit & Features

    • Floral pattern, mesh lined fabric
    • Orchid inset, halter cowl neckline, tie straps
    • Open back design
    • Crop-length hem
    • Runs true to size

    Style Number/Barcode: 06001-000468

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Delicate and Daring Strappy Crop Top

    This beaded hanky hem top contours through the bodice, dips into a V-neckline, and ties across the open back for a barely-there finish that pairs perfectly with tailored pants or a sleek mini skirt.

    Fit & Features

    • Mesh-lined fabric with beaded detailing
    • V-neckline with slim adjustable straps
    • Fitted bodice with hanky hem
    • Open back with adjustable tie closure
    • Runs true to size

    Style Number/Barcode: 06001-000486

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: BROWN, CHARTREUSE, PLUM

    Available Size: XS, S, M, L

    Product Badge:
    • Back In Stock
  • Floral Confidence Maxi Skirt

    It’s the kind of skirt that makes sunset cocktails turn into dinners with a view. The floral maxi skirt features a fluid drape, statement silhouette, and flared hem that feels flirty, elevated, and ready for warm nights out.

    Shop The Matching Top: Floral Confidence Halter Crop Top

    Fit & Features

    • Tropical statement floral print
    • Mesh fabric with smooth knit lining
    • Mid-rise waist
    • Curve-hugging
    • Maxi flared hem
    • Runs true to size

    Style Number/Barcode: 06501-000116

    Category Name: Vacation Looks

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BANANA

    Available Size: L

    Product Badge:
    • Sale