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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.

  • Day to Night Clear Wedges

    These chic wedges are a wardrobe essential! The wedges feature a square toe, a PVC strap and an adjustable ankle strap. Style them with a midi dress and a boyfriend blazer for the perfect day to night look.

    Fit & Features

    • Square toe
    • Clear PVC Strap
    • Wedges
    • Fits true to size

    Style Number/Barcode: 07406-0250

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek And Trendy Aviator Sunglasses

    Sleek and trendy, these sunglasses are a must-have for the summer season. They feature an angled aviator design, a silver metal frame, and tinted lenses. Style these shades with a graphic tee and denim shorts.

    Fit & Features

    • Angled aviator design
    • Silver metal frame
    • Tinted lenses
    • 100% UV Protection

    Style Number/Barcode: 07008-0874

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Dream Tassel Earrings

    Add a boho touch to your look with these tassel earrings. They feature a metal bamboo circle post with an attached tassel fringe. Pair them with a tropical print matching set and sandals.

    Fit & Features

    • Metal bamboo circle post
    • Tassel fringe
    • Post-back closure


    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged

    Style Number/Barcode: 07001-0567

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bikinis And Bellinis Graphic Tube Top

    The perfect graphic tube top for summer parties! This trendy style features a strapless neckline, ruching, a fitted mid-length hem, and a script that reads, "Bikinis & Bellinis."

    Fit & Features

    • Knit fabric, moderate stretch
    • Strapless straight-across neckline
    • Front script reading, "Bikinis & Bellinis"
    • Ruching
    • Fitted mid-length hem
    • Runs true to size

    Style Number/Barcode: 06002-000147

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Fab Find Oversized Sunglasses

    These trendy shades are a fab find for the summer season! The sunglasses feature an oversized square-shaped design, a plastic frame with open side details, and tinted lenses. Style these sunnies with a floppy hat.

    Fit & Features

    • Oversized square-shaped design
    • Plastic frame, open side details
    • Tinted lenses
    • 100% UV Protection

    Style Number/Barcode: 07008-0875

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fun And Fierce Espadrille Wedges

    Get a fun and fierce vibe for the summer with these cute wedges! They feature an open round toe with a toe strap, an adjustable ankle strap, a trendy cheetah print, and an espadrille wedge heel. Style these shoes with a casual dress and cat-eye sunglasses.

    Fit & Features

    • Open round toe, toe strap
    • Adjustable ankle strap, buckle detail
    • Heel strap
    • Cheetah print
    • Espadrille wedge heel
    • Runs true to size

     

    Style Number/Barcode: 07406-0275

    Category Name: Vacation Looks

    Price: $7.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Snapshot Floral Mesh Mini Skirt

    Get the best pics for the gram in this stunning mesh mini skirt featuring a high-rise waist, short curve-hugging fit, and large floral print pattern.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Large floral print
    • High-rise waist
    • Mini-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-000057

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual And Chic Slides

    These trendy slides will give you a casual-chic vibe for the summer! They feature an open round toe, a faux leather wide toe strap with a scrunched design, and a flat sole. Style these shoes with a cute crop top and denim shorts.

    Fit & Features

    • Open round toe
    • Faux leather wide toe strap, scrunched design
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-0765

    Category Name: Vacation Looks

    Price: $10.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fab And Trendy Heart-Shaped Sunglasses

    Fall head over heels for these fab sunglasses that will give you a trendy look! They feature a heart-shaped design with a plastic trim and tinted lenses. Style these shades with your fave bikini for a beach trip with the squad.

    Fit & Features

    • Heart-shaped design
    • Plastic trim
    • Tinted lenses
    • 100% UV Protection

    Style Number/Barcode: 07008-0870

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High Slit Maxi Knit Skirt

    Keep it effortlessly stylish with a skirt that is perf for your next beach day! The skirt features a high-rise waist, a high side slit, and a maxi-length silhouette. The skirt is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with a crop top. 

    Fit & Features

    • High rise waist
    • High side slit
    • Maxi length silhouette 
    • Knit fabric 
    • Form hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-0419

    Category Name: Vacation Looks

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bohemian Dreams Paisley Print Headwrap

    Channel those dreamy vibes with a paisley headwrap that keeps tresses relaxed and stylish. The headwrap is composed of mesh fabric and has an oversized-fit wrap-around design. Complete the look with the matching swim cover-up, bikini top, and bikini bottoms.

    Shop Matching Swim Coverup: Bohemian Dreams Ruched Paisley Print Swim Coverup

    Shop Matching Bikini Top: Bohemian Dreams Paisley Print Bikini Top

    Shop Matching Bikini Bottoms: Bohemian Dreams Paisley Print Bikini Bottoms

    Fit & Features

    • Wrap-around design
    • Paisley print
    • Mesh material

    Style Number/Barcode: 07305-0301

    Category Name: Vacation Looks

    Price: $8.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer-Ready Platform Mules

    These boho-chic platform mules will have you totally summer-ready! They feature an open round toe, a double-banded design, and a tall platform and block heel with a stunning multi-colored woven pattern. Style these mules with a breezy maxi dress for your next weekend getaway.

    Fit & Features

    • Open round toe
    • Double-banded design, faux microsuede material
    • Tall platform and block heel
    • Multi-colored woven pattern
    • Runs true to size

     

    Style Number/Barcode: 07401-3096

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Whisked Away Wide-Leg Pants

    Get whisked away in these chic pants! The pants feature a high-rise waist, straight leg, and a wide-leg hem. Complete the look with the matching top and wedges for your Hampton's ready look!

    Shop Matching Top: Boho-Chic Convertible Crop Top

    Fit & Features

    • High-rise elastic banded waist
    • Pleated detailing
    • Straight leg 
    • Wide-leg hem
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06502-0753

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Romanced By Ruffles Chiffon Floral Dress

    Bring the romance with a ruffled mini dress! The dress features a sleeveless V-neckline, adjustable spaghetti straps that cross at the back, a floral print, tiered ruffles, and a mini-length silhouette. The dress is composed of a lined chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, cross at back
    • Floral print
    • Tiered ruffles
    • Lined chiffon fabric 
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 05101-0648

    Category Name: Vacation Looks

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Glam Tropical Maxi Dress

    Dazzle with an island-inspired look in this maxi dress that brings those vacay vibes! The dress features a sleeveless V-neckline, spaghetti straps, a tropical floral print, a high side slit, and a maxi length silhouette. Complete look with wedges and a floppy hat. 

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Tropical floral print
    • High side slit
    • Maxi length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05101-0318

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fab And Fresh Floral Tie Front Top

    Keep it fresh with a trendy tie-front top that keeps your look on point! The top features a plunging V-neckline, tie-front accent, short sleeves, cropped hem, and a ditsy floral print. Complete the look with the flared pants. 

    Shop Matching Pants: Fab And Fresh Floral Flared Pants

    Fit & Features

    • V-neckline
    • Tie-front 
    • Short sleeves
    • Cropped hem
    • Ditsy floral print
    • Form hugging fit, runs true to size

    Style Number/Barcode: 06202-0191

    Category Name: Vacation Looks

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Bound Ruched Tropical Romper

    Make a tropical escape with this cute romper! The romper features a sweetheart neckline with a ruched tie front, fluttery cap sleeves, a smocked back, tropical print, and cheeky wide-leg shorts. Complete look with wedges and tassel earrings. 

    Fit & Features

    • Sweetheart neckline
    • Cap sleeves
    • Smocked back
    • Tropical print
    • Cheeky wide leg shorts
    • Form hugging fit
    • Runs true to size

    Style Number/Barcode: 06303-0103

    Category Name: Vacation Looks

    Price: $15.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunset Stunner Asymmetrical Midi Dress

    This dress will have you looking stunning as you watch the sunset on your next vacay! It features a sleeveless V-neckline, adjustable spaghetti straps, a beautiful tropical floral print, and a mid-length, curve-hugging silhouette with an asymmetrical hem. Style this dress with hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Back cross-back design
    • Ruched detailing
    • Mid-length, form-hugging fit, asymmetrical hem
    • Knit fabric, moderate stretch, tropical floral print
    • Runs true to size

    Style Number/Barcode: 05102-1860

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Getaway Lace-Up Espadrille Wedges

    These chic espadrille wedges are the perfect excuse for a weekend getaway! They feature a trendy closed square toe and lace-up ankle straps that let you customize the look.

    Fit & Features

    • Espadrille wedge heel
    • Closed square toe
    • Lace-up ankle straps
    • Runs true to size

    Style Number/Barcode: 07406-000025

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: TAN

    Available Size: 10

    Product Badge:
    • Sale
  • Floral Fever Ribbed Knit Mini Dress

    Keep it stylish with a floral dress that is all the rage! The dress features a sleeveless sweetheart neckline, spaghetti straps, a tie-front at the bust, a ditsy floral print, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps
    • Tie-front 
    • Ditsy floral print 
    • Mini-length silhouette 
    • Ribbed knit fabric, form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-2032

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic High-Slit Basic Maxi Dress

    Basic yet oh-so-chic, this sleeveless maxi dress will be your new go-to. It features a crew neckline, tank shoulder straps, a sultry thigh-high side slit, and a floor-length fitted silhouette. Style this dress with sleek hoop earrings.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Thigh-high side slit
    • Floor-length fitted silhouette
    • Ribbed cotton fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4090

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sealed In Chic Tie Front Top

    Seal in a chic look with this cute tie-front top! The top features a plunging V-neckline, a cinching tie-front, short sleeves, and a cropped hem. Complete look with high waist shorts and platform wedges. 

    Fit & Features

    • V-neckline
    • Tie-front
    • Short sleeves
    • Cropped hem 
    • Form hugging fit
    • Runs true to size

    Style Number/Barcode: 06204-0903

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dreaming Of Paradise Maxi Skirt

    This beautiful maxi skirt will have you dreaming of jetting off to paradise! It features a high-rise waist, a chic thigh-high front slit, a flowy silhouette, and a trendy all-over tropical leaf print. Style this skirt with a crop top and a floppy hat for a vacay-ready look!

    Fit & Features

    • High-rise elastic banded waist
    • Thigh-high front slit
    • Flowy fit
    • Knit fabric, moderate stretch, tropical leaf print
    • Runs true to size

    Style Number/Barcode: 06501-0445

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stunning Beauty Floral Jumpsuit

    Showcase your stunning beauty in this blooming floral printed jumpsuit. It features a strapless square neckline, a high waist, front pockets, and a wide-leg fit. Style this jumpsuit with clear heels for a summer party.

    Fit & Features

    • Strapless square neckline
    • High waist
    • Front pockets
    • Wide-leg fit
    • Knit fabric, floral print
    • Runs true to size

    Style Number/Barcode: 06502-0592

    Category Name: Vacation Looks

    Price: $16.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free