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
  • Summer Crush Striped Crochet Midi Skirt

    POV: you just found your new fave beach-to-brunch vibe. This striped crochet midi skirt serves laid-back heat with a form-hugging fit and thigh-high slit made for turning heads from sunrise to sunset.

    Shop Matching Top: Summer Crush Striped Crochet Bralette Top

    Fit & Features

    • Crochet knit fabric
    • Striped pattern
    • High-rise waist
    • Thigh-high side slit
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-000027

    Category Name: Vacation Dresses & Outfits

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • 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: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sun-Kissed Moments Tie-Strap Bikini Bottoms

    You'll have sun-kissed moments in these trendy low-rise bikini bottoms featuring tie straps on each side with beaded detailing. Style with the matching bikini top.

    Shop Matching Top: Sun-Kissed Moments Triangle Bikini Top

    Fit & Features

    • Nylon-blend fabric, high stretch
    • Low-rise waist
    • Tie straps on each side, beaded details
    • Cheeky fit
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000009

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: L

  • Wild Card Leopard Floral Print Maxi Skirt

    This skirt’s got plot twist energy—sweet florals meet fierce leopard in a ruffled maxi made for your wild side. Let the bold print and thigh-high slit steal the spotlight from brunch to beach nights.

    Fit & Features

    • Sheer mesh fabric with mini-length knit lining, high stretch
    • Leopard and floral multi-print pattern
    • High-rise waist
    • Ruching, hip-hugging fit
    • Thigh-high side slit, ruffled hem
    • Maxi-length hem, flowy silhouette
    • Runs true to size

    Style Number/Barcode: 06501-000061

    Category Name: Vacation Dresses & Outfits

    Price: $36.90

    Availability: In Stock

    Available Color: LEOPARD

    Available Size: S, M, L

  • Coastal Crush Starfish And Pearl Drop Earrings

    Giving mermaid-core in the cutest way possible. These starfish drop earrings with faux pearls are your new fave vacation plus-one—just add salty waves and a sundress.

    Fit & Features

    • Textured metal starfish stud detail
    • Faux pearl drop with glossy finish
    • Lightweight dangle silhouette
    • Push-back post closure


    Earrings are final sale and may not be returned or exchanged

    Style Number/Barcode: 07001-000127

    Category Name: Vacation Dresses & Outfits

    Price: $7.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • Wildflower Energy Cowl Halter Romper

    This sheer mesh halter romper mixes floral and animal vibes for a look that’s flirty, fierce, and ready for your next night out!

    Fit & Features

    • Floral and leopard mix print, mesh-lined fabric
    • Halter cowl neckline, spaghetti strap tie
    • Open strappy back
    • Built-in mini shorts with flirty skirt overlay
    • Curve-hugging fit
    • Runs true to size

    Style Number/Barcode: 06503-000082

    Category Name: Vacation Dresses & Outfits

    Price: $39.90

    Availability: In Stock

    Available Color: LEOPARD

    Available Size: XS, M

    Product Badge:
    • Best Seller
  • 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

    Product Badge:
    • Ships Free
  • Sea You Later Chain Belt

    Giving mermaid off-duty energy. This chain belt brings all the coastal cuteness with starfish and shell accents—wear it poolside, seaside, or whenever you’re channeling beach babe vibes.

    Fit & Features

    • Chain-link design
    • Starfish and shell accents
    • Adjustable fit with lobster clasp closure

    Style Number/Barcode: 07301-000139

    Category Name: Vacation Dresses & Outfits

    Price: $18.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • 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
  • Savor The Moment Halter Cutout Maxi Dress

    Step into the spotlight in this halter maxi dress on vacation or for some summer fun! Featuring a striking halter neckline adorned with elegant hardware and a shimmering stone insert, this bodycon dress offers a bold cutout design that highlights your figure.

    Fit & Features

    • Smooth knit stretchy fabric
    • Halter neckline with tie closure
    • Hardware and stone insert
    • Cutout accents
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000030

    Category Name: Vacation Dresses & Outfits

    Price: $39.90

    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
  • Such A Delight Bow Flat Sandals

    Perfect for the beach or any casual plans, these flat sandals will delight with a charming bow strap and comfortable footbed. 

    Fit & Features

    • Square toe
    • H-shaped band with bow
    • Cushioned insole
    • Faux leather material
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1288

    Category Name: Vacation Dresses & Outfits

    Price: $18.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: 6, 7.5, 9

  • 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

    Product Badge:
    • Ships Free
  • Getaway Girlie Halter Bead Crochet Mini Dress

    Your next getaway calls for this crochet mini dress! This dress has a stunning halter bead neckline that adds a touch of boho, a cutout accent, and a flattering bodycon silhouette.

    Fit & Features

    • Crochet lined fabric
    • Halter beaded neckline, spaghetti strap ties
    • Padded bra cups
    • Back zipper hook-eye closure, lower ruched seam
    • Cutout front accent
    • Bodycon silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6116

    Category Name: Vacation Dresses & Outfits

    Price: $44.90

    Availability: In Stock

    Available Color: MINT

    Available Size: XS, S, M

    Product Badge:
    • Best Seller
  • 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
  • Poolside Paradise Floral Triangle Bikini Top

    So pretty and made for tanning, this floral bikini top offers flattering triangle-shaped cups and dual spaghetti strap ties that let you customize the style! Pair with the matching bikini bottoms.

    Shop Matching Bottoms: Poolside Paradise Floral Scrunch Bikini Bottoms

    Fit & Features

    • Floral print, stretchy knit fabric
    • V-shaped low-rise waist
    • Scrunched thong back coverage
    • Runs true to size

    Style Number/Barcode: 07104-000007

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Scandal Tropical Cutout Maxi Dress

    Booked the trip? Now bring the drama in this tropical maxi dress! With metal hardware and skin-baring cutouts, this maxi is not for blending in—it's bold, body-hugging, and built for after-hours.

    Fit & Features

    • Tropical print, mesh fabric, smooth stretchy knit lining
    • Halter neckline with hardware accents, spaghetti strap tie
    • Bandeau-style cutout bodice with center metal U-ring
    • Ruched high waist with hardware accent
    • High front slit on a body-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000032

    Category Name: Vacation Dresses & Outfits

    Price: $20.97 $45.90

    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 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

    Product Badge:
    • Ships Free
  • 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: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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