Vacation Dresses & Outfits

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STYLE SPOTLIGHT

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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.

  • Casually Cool Slit Maxi Dress

    Stroll outside looking casually cool and cute in this basic maxi dress design with a sleeveless scoop neck with bungee spaghetti straps, a form-hugging silhouette, and a high-cut side slit. Complete the look in a crop denim jacket and sneakers.

    Fit & Features

    • Sleeveless scoop neck
    • Bungee spaghetti straps
    • Form-hugging
    • High-cut side slit
    • Maxi-length hem
    • Rib-knit fabric, lined, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4883

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Darling Woven Drop-Waist Skater Dress

    Create a sweet summer look that is oh-so-darling with this drop-waist skater dress. Designed with a lightweight woven fabric, the bodice is accented with a dainty lace trim for a pretty vibe. The short dress features a sleeveless sweetheart neckline, a ruched bust with a small tie-front adjustable detail, and thin tank straps leading to an alluring lace-up back for a customized fit. The asymmetric drop-waist is detailed with pleated side panels, flowing down to a tiered A-line silhouette for a flirtatious look. Style with hoop earrings and a charm necklace.

    Fit & Features

    • Woven fabric with lace trim woven lining
    • Sweetheart neckline, ruched bust, adjustable tie-front
    • Tank straps, lace-up back design
    • Back zipper and hook-eye closure
    • Asymmetric drop-waist, pleated side panels
    • Tiered A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3378

    Category Name: Vacation Dresses & Outfits

    Price: $64.90

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: L

  • So Darling Woven Drop-Waist Skater Dress

    Create a sweet summer look that is oh-so-darling with this drop-waist skater dress. Designed with a lightweight woven fabric, the bodice is accented with a dainty lace trim for a pretty vibe. The short dress features a sleeveless sweetheart neckline, a ruched bust with a small tie-front adjustable detail, and thin tank straps leading to an alluring lace-up back for a customized fit. The asymmetric drop-waist is detailed with pleated side panels, flowing down to a tiered A-line silhouette for a flirtatious look. Style with hoop earrings and a charm necklace.

    Fit & Features

    • Woven fabric with lace trim woven lining
    • Sweetheart neckline, ruched bust, adjustable tie-front
    • Tank straps, lace-up back design
    • Back zipper and hook-eye closure
    • Asymmetric drop-waist, pleated side panels
    • Tiered A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3377

    Category Name: Vacation Dresses & Outfits

    Price: $64.90

    Availability: In Stock

    Available Color: WHITE, SAGE

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

  • Meet In The Hamptons Linen Wide Leg Pants

    These linen wide-leg pants have a Hampton's getaway written all over it! Look cute strolling through the town in these pants featuring a flattering high-rise waist and a hidden back zipper closure. Style with the matching top and a dainty necklace to complete the chic look!

    Shop Matching Top: Meet In The Hamptons Linen Crop Top

    Fit & Features

    • High-rise waist
    • Hidden back zipper closure
    • Wide-leg silhouette
    • Lined linen fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0723

    Category Name: Vacation Dresses & Outfits

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunlight Dream Floral Paisley Silk Scarf

    Create a dreamy daytime vibe with this silk scarf featuring a blooming floral paisley print and multiple styling options! Complete the look with a basic bodysuit, jeans, and a coffee in hand to stroll the streets of a cute downtown area.

    Fit & Features

    • Floral paisley print
    • Silky material
    • Multiple styling options

    Style Number/Barcode: 07305-0450

    Category Name: Vacation Dresses & Outfits

    Price: $4.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

  • Cuddle Time Chenille Crop Cardigan

    Wrap yourself in this chenille crop cardigan for a cute and cuddly vibe! The sweater features long sleeves, a ribbed open-front design, and a cropped hem on ultra-soft and cozy chenille knit fabric. Complete the look in the matching cozy pajama top and bottoms for a chill night in!

    Shop Matching Pajama Top: Chill Night Chenille Crop Tank Top

    Shop Matching Pajama Bottoms: Feeling The Vibe High-Rise Chenille Joggers

    Fit & Features

    • Long sleeves
    • Ribbed open-front design
    • Cropped hem
    • Ultra-soft and cozy 
    • Chenille knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 07103-0946

    Category Name: Vacation Dresses & Outfits

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Arrived In Style Chiffon Sheer Kimono

    Arrive wherever you're headed in this stylish chiffon sheer kimono to elevate your outfit! It features breezy short sleeves, an open front design, side slit accents, and a flowy mid-calf length hem. Layer over a crop top, shorts, and sassy lace-up heels to complete your look!

    Fit & Features

    • Breezy short sleeves
    • Open front design
    • Side slit accents
    • Flowy mid-calf length hem
    • Sheer, airy chiffon fabric
    • Runs true to size

    Style Number/Barcode: 06204-1333

    Category Name: Vacation Dresses & Outfits

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Smoke And Mirrors Square Sunglasses

    No matter your mood, these square sunglasses are perfect for slipping on when you can't even! They feature a sleek metal frame with cool, smokey pink-tinted lenses and rubber nose supports. Complete the look in a flirty printed sundress for a day out.

    Fit & Features

    • Square sleek metal frame
    • Rubber nose supports
    • Smokey pink tinted lenses

    Style Number/Barcode: 07008-1006

    Category Name: Vacation Dresses & Outfits

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

  • Coastal Babe Slip-On Wedge Sandals

    For strolls along the coast or any weekend adventure, these slip-on wedge sandals provide comfort and style! They feature a square toe, a wide strap, and a platform sole of faux leather material. Complete the look with cute sunglasses.

    Fit & Features

    • Square toe, wide strap
    • Platform sole
    • Wedge style
    • Slip-on and off styling
    • Faux leather material, cushioned insole
    • Runs true to size

    Style Number/Barcode: 07404-1093

    Category Name: Vacation Dresses & Outfits

    Price: $12.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sangria Please Striped Halter Top

    Can't you imagine wearing this striped halter top while sipping on a sangria? Set the tone this vacay-ready crop top featuring a sleeveless, halter neck, tie-closure, striped pattern, and a smocked back. Complete the look in the matching bottoms.

    Shop The Matching Bottoms: Sangria Please Striped Wide Leg Pants

    Fit & Features

    • Sleeveless, halter neck, tie-closure
    • Cropped hem
    • Smocked back
    • Striped pattern
    • Gauze woven fabric, no stretch, fits true to size

    Style Number/Barcode: 06003-1568

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wandering Bliss Halter Crochet Jumpsuit

    Wander in bliss looking so boho in this sleeveless jumpsuit perfect for a music festival or summer vacation! It features a halter V-neckline with tie closure, an open back, a crochet waist, and a flowy wide-leg silhouette on gauze-woven fabric. Complete the look n espadrille wedges.

    Fit & Features

    • Sleeveless halter V-neckline, tie closure
    • Open back
    • Crochet waist
    • Wide-leg silhouette
    • Gauze woven fabric
    • No stretch
    • Runs true to size

    Style Number/Barcode: 06302-0724

    Category Name: Vacation Dresses & Outfits

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Staple Faux Fur Ankle Booties

    Fit & Features

    • Flat sole
    • Ankle-fit
    • Almond toe
    • Faux suede exterior
    • Faux fur lined insole
    • Runs true to size

    Style Number/Barcode: 07408-0114

    Category Name: Vacation Dresses & Outfits

    Price: $28.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glow Up Button-Front Cropped Vest

    Hit the scene in the glow up button-front cropped vest. This ribbed knit piece flaunts a sleeveless V-neckline and a chic button-front. Perfect for adding a touch of glam to any outfit.

    Fit & Features

    • Lurex knit fabric
    • Sleeveless V-neckline
    • Single button-front closure
    • Fitted cropped ribbed hem
    • Runs true to size

    Style Number/Barcode: 06005-2149

    Category Name: Vacation Dresses & Outfits

    Price: $26.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: XS, S, M, L

  • Cozy Bliss Faux Fur Bucket Hat

    Fit & Features

    • Oversized bucket design
    • Faux fur fabrication

    Style Number/Barcode: 07302-1734

    Category Name: Vacation Dresses & Outfits

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

  • Party Hour Rhinestone Beer And Lime Earrings

    Dive into fun with these rhinestone beer and lime earrings. Featuring a lime slice post and sparkling beer bottle design, these earrings are your perfect party pals. Cheers to style!

    Fit & Features

    • Lime slice post
    • Hanging beer bottle design
    • Mini rhinestone embellishments
    • Post-back closure

     

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

    Style Number/Barcode: 07001-2321

    Category Name: Vacation Dresses & Outfits

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Luxe Lurex Knit Pants

    Get cozy in the luxe lurex knit pants. With a mid-rise drawstring waist and straight-leg fit, these pants are your go-to for effortless style and comfort.

    Fit & Features

    • Lurex knit fabrication
    • Mid-rise waist
    • Drawstring waist
    • Straight-leg fit
    • Runs true to size

    Style Number/Barcode: 06502-2556

    Category Name: Vacation Dresses & Outfits

    Price: $44.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: XS, S, M, L

  • Pretty Aura Floral Print Strapless Crop Top

    Nail your look with cute jeans and this floral print strapless crop top. Featuring a V-cut insert and ruching, this flirty piece hugs your curves and brings all the vibes.

    Fit & Features

    • Lined knit fabric with plenty of stretch
    • Large floral print
    • Strapless neckline with V-cut insert
    • Ruching
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5552

    Category Name: Vacation Dresses & Outfits

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coastal Chic Starfish Dangle Earrings

    Fit & Features

    • Dangle design
    • Textured starfish charm
    • Fish hook closure

     

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

    Style Number/Barcode: 07001-2329

    Category Name: Vacation Dresses & Outfits

    Price: $7.90

    Availability: Out of Stock

  • Cutely Charming One-Shoulder Crop Top

    Go ahead and strut your cute and charming self in this sleeveless crop top to elevate your basics collection! It boasts a one-shoulder neckline with a cinch detail, and a fitted crop hem on stretchy rib knit fabric. Complete the look in a denim midi skirt and sandals!

    Fit & Features

    • Stretchy rib knit fabric
    • One-shoulder neckline
    • Tank strap with cinch detail
    • Fitted crop length hem
    • Runs true to size

    Style Number/Barcode: 06002-1909

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fierce Allure Leopard Print Mesh Maxi Dress

    Flaunt a fierce allure in this curve-hugging leopard print maxi dress! The airy sheer mesh fabric lined with knit offers plenty of stretch and showcases a leopard print pattern for a sultry-chic vibe. The long dress features a sleeveless V-neckline, spaghetti straps, a form-fitting silhouette to accent your gorgeous curves, and a maxi-length hem. Style with strappy mules for a rooftop happy hour.

    Fit & Features

    • Leopard print
    • Sheer mesh fabric with knit lining, plenty of stretch
    • V-neckline
    • Spaghetti straps
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05101-3328

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wildly Sultry Tie-Front Leopard Rose Mesh Crop Top

    Wildly sultry is exactly how you'll look in this leopard rose mesh crop top on a night out!  The flared long sleeves and V-neckline with tie closure give a playful touch, while the center slit adds a touch of allure. The cropped length and striking leopard rose print make this top a must-have for any bold fashionista. Complete the look with the matching skirt.

    Shop Matching Bottoms: Wildy Sultry High Rise Leopard Floral Maxi Skirt

    Fit & Features

    • Leopard rose print, sheer mesh fabric, moderate stretch
    • Flared long sleeves
    • V-neckline
    • Tie-front closure and center slit
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06202-0472

    Category Name: Vacation Dresses & Outfits

    Price: $29.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 50s Icon Halter Plunge Neck Skater Romper

    Chanel a popular 50s iconic look in this halter plunge skater romper perfect for themed parties or summer holidays! With a flattering halter neckline and charming tie closure, this romper will create a stunning silhouette. The skater shape and short hem add to its playful appeal. Complete the look with hoop earrings.

    Fit & Features

    • Smooth cotton-blend knit fabric, moderate stretch
    • Halter plunge neckline, tie closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 06503-1138

    Category Name: Vacation Dresses & Outfits

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK, BROWN

    Available Size: XS, S, M, L

  • Wildy Sultry High Rise Leopard Floral Maxi Skirt

    Wildly sultry is exactly how you'll look in this leopard rose mesh maxi skirt on a night out! The skirt boasts a flattering high-rise waist complimented by a bodycon silhouette that accentuates your curves along the midi-length hem. Complete the look with the matching top.

    Shop Matching Top: Wildly Sultry Tie-Front Leopard Rose Mesh Crop Top

    Fit & Features

    • Leopard floral print, mesh fabric lined with stretchy knit
    • High-rise waist
    • Hip-hugging fit
    • Maxi-length 
    • Runs true to size

    Style Number/Barcode: 06501-1052

    Category Name: Vacation Dresses & Outfits

    Price: $36.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Grandeur Blooms Strapless Slit Floral Maxi Dress

    Gorgeous blooms dance across this floral maxi dress making every entrance statement worthy! Perfect for cocktail parties or dressy dinners, this strapless dress boasts a form-hugging fit, a high side slit allowing for movement, and a maxi-length hem. Complete the look with a clutch purse and heels.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • Strapless neckline
    • High side slit
    • Form-hugging fit
    • Runs true to size
    • Please note flower placement may vary

    Style Number/Barcode: 05101-4107

    Category Name: Vacation Dresses & Outfits

    Price: $39.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, L