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.

  • Sweet For The Summer Babydoll Dress

    Sweet and chic, this babydoll dress is perf for the summer season. It features a square neckline, three-quarter length puff sleeves with cute ruffled hems, a high waist seam, and a short, flowy, flared-out silhouette. Style this dress with a trendy shoulder bag and mules for a weekend brunch.

    Fit & Features

    • Square neckline
    • Three-quarter length puff sleeves, ruffled elastic cinched hems
    • Stretchy smocked back detail, high waist seam
    • Mini-length silhouette
    • Flowy, flared-out fit
    • Twill fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4109

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flared Glamour Tie Front Top

    Bring the flare with a cute tie-front top! The top features a plunging V-neckline, a tie-front accent, long bell sleeves, and a cropped hem. The top is composed of a crepe fabric that offers a relaxed fit with a moderate stretch. Complete look with high waist shorts. 

    Fit & Features

    • Plunging V-neckline
    • Tie-front accent
    • Long bell sleeves
    • Cropped hem 
    • Crepe fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06204-0887

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry-Chic Style Mini Dress

    Elevate your style with this sultry-chic mini dress! It features a sleeveless deep V-neckline, spaghetti straps, sexy cutouts at the waist, and a short, form-hugging fit that will hug your curves. Complete the look with sleek earrings and cute mules.

    Fit & Features

    • Sleeveless deep V-neckline
    • Spaghetti straps
    • Cutouts at the waist
    • Mini-length, form-hugging silhouette
    • Ribbed knit fabric, smooth knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4119

    Category Name: Vacation Looks

    Price: $5.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Cuts Perforated Block Heels

    Stay on the cutting edge with chic heels! The heels feature an open back, a wide adjustable ankle strap, a perforated pattern body, a peep toe, and a block heel. The heels are composed of a faux nubuck material. Complete look with a romper and a dainty butterfly charm anklet. 

    Fit & Features

    • Open back 
    • Wide adjustable ankle strap
    • Perforated pattern body
    • Peep toe
    • Block heel
    • Faux nubuck material 

    Style Number/Barcode: 07403-1321

    Category Name: Vacation Looks

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Faux Leather Quilted Chic Sneakers

    Lace-up in glam sneakers to keep it chic and sporty! The sneakers feature a lace-up front, an almond toe, a quilted diamond design, and a wide sole. The sneakers are composed of a faux leather material. Complete look with a crop top and biker shorts. 

    Fit & Features

    • Lace-up front
    • Almond toe
    • Quilted diamond design 
    • Wide sole 
    • Faux leather material

    Style Number/Barcode: 07407-0206

    Category Name: Vacation Looks

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Butterfly Printed Satin Scarf

    Style up your pretty tresses with a chic printed scarf! This scarf is composed of a lightweight satin material and features a trendy all-over butterfly pattern. Complete the look with cute sunglasses.

    Fit & Features

    • Satin material
    • Butterfly print

    Style Number/Barcode: 07305-0306

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Vibes Platform Block Heels

    Style your weekend outfits with these adorable block heels for stylish looks this summer! They feature an open round toe with a toe strap, an adjustable ankle strap, and a trendy cork platform and block heel. Style these shoes with cute sunglasses.

    Fit & Features

    • Open round toe, faux leather toe strap
    • Faux leather adjustable ankle strap, buckle detail
    • Open back
    • Cork platform and block heel
    • Runs true to size

    Style Number/Barcode: 07401-3285

    Category Name: Vacation Looks

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Rhinestone Butterfly Earrings Set

    Get a pretty and glamorous look with this adorable earring set! It features three pairs of earrings, including a pair of dainty rhinestone studs, rhinestone embellished butterfly-shaped studs, and sleek small hoops with rhinestone butterfly charms. Style these earrings with a trendy ring set.

    Fit & Features

    • Three pairs of earrings
    • Rhinestone studs, post back closures
    • Rhinestone butterfly studs, post back closures
    • Small hoops with rhinestone butterfly charms, omega closures


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

    Style Number/Barcode: 07001-0841

    Category Name: Vacation Looks

    Price: $5.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Days Platform Heels

    These adorable platform heels were made for sunny days! They feature an open almond-shaped toe, a faux leather braided toe strap, a faux leather adjustable ankle strap, and a cork platform and block heel. Style these shoes with your fave floral dress.

    Fit & Features

    • Open almond-shaped toe
    • Faux leather braided toe strap
    • Faux leather adjustable ankle strap, buckle detail
    • Open back
    • Cork platform and block heel
    • Runs true to size

    Style Number/Barcode: 07401-3297

    Category Name: Vacation Looks

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lookin' Fab Floral Maxi Dress

    Style up this adorable floral maxi dress for a fab summertime look! It features a sleeveless V-neckline, adjustable spaghetti straps, front ruched detailing, a fitted bodice leading to a flowy silhouette, and a high front slit. Complete the look with chic mules.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, back zipper closure
    • Front ruching
    • Fitted bodice leading to a flowy silhouette
    • High front slit
    • Chiffon fabric, ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05101-1117

    Category Name: Vacation Looks

    Price: $20.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Evil Eye Rhinestone Choker Set

    Ward off bad vibes with this choker set that brings positive energy! The choker set includes a rhinestone choker, a snake chain choker, a dainty chain link choker with rhinestone evil eye charm, and a fringe choker. Complete look with a white mini dress and mules.

    Fit & Features

    • Set includes 4 chokers
    • Snake chain
    • Rhinestones
    • Evil eye charm
    • Fringe 
    • Lobster clasp closure 

    Style Number/Barcode: 07002-0753

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropic Like It’s Hot Wide Leg Cowl Neck Jumpsuit

    This tropical jumpsuit keeps it cool with a strappy open back and wide-leg silhouette perfect for rooftop dates or vacay nights!

    Fit & Features

    • Tropical print, smooth knit stretchy fabric
    • Halter cowl neckline, spaghetti strap tie, bust knit lining
    • Open back with spaghetti strap tie
    • Flowy wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-000029

    Category Name: Vacation Looks

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Instant Classic Faux Suede Platform Block Heels

    These heels are an instant classic, babe! The heels feature an open back, an adjustable ankle strap, an open almond toe with a wide strap over the toe, a wide platform, and a block heel. The heels are composed of a faux suede material. Complete look with a bodysuit and mini skirt. 

    Fit & Features

    • Open back 
    • Adjustable ankle strap
    • Open almond toe, wide strap over the toe
    • Wide platform
    • Block heel
    • Faux suede material 

    Style Number/Barcode: 07401-3205

    Category Name: Vacation Looks

    Price: $16.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always On-Trend Lug Sole Platform Heels

    You're always on top of the latest trends, so you def can't pass up these chic platform heels. They feature an open almond-shaped toe with a toe strap, an adjustable ankle strap, a platform with a lug sole, and a tall block heel. Style these faux leather heels with a cute jumpsuit for happy hour.

    Fit & Features

    • Open almond-shaped toe
    • Toe strap
    • Adjustable ankle strap, buckle detail
    • Platform, lug sole
    • Tall block heel
    • PU material
    • Runs true to size

    Style Number/Barcode: 07401-3294

    Category Name: Vacation Looks

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Gorgeous Glam Layered Belly Chain Set

    Accessorize your poolside look with these glam belly chains for a gorgeous vibe! The set features three belly chains in a layered design with a twisted chain, a thin flat chain, and a thicker chain. Style this set with your fave bikini and trendy shades.

    Fit & Features

    • Belly chain set
    • Three-row layered design
    • Twisted chain
    • Thin flat chain
    • Thicker chain
    • Adjustable lobster clasp closures

    Style Number/Barcode: 07002-0883

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Layered Luxe Swag Chain Belt

    Layer on the luxe with a stylish swag chain belt! The belt features a triple-row design and chunky chain links. Includes a lobster clasp closure. Complete look with a matching top and skirt set and clear heels. 

    Fit & Features

    • Triple-row
    • Swag chain design 
    • Chunky chain link
    • Lobster clasp closure 

    Style Number/Barcode: 07301-0323

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Faux Suede Double Buckle Slip On Sandals

    Slip on these stylish sandals that feature a slip-on design, an open almond toe, a double row of straps with buckle, toe loop, and a cork sole. Complete look with a romper and trendy scrunchie. 

    Fit & Features

    • Slip-on design 
    • Double row of straps with buckle
    • Toe loop
    • Cork sole
    • Faux microsuede

    Style Number/Barcode: 07404-0866

    Category Name: Vacation Looks

    Price: $12.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Days Criss Cross Espadrille Wedges

    Keep it lowkey stylish this season with wedges to pair with your favorite floral dresses! The wedges feature an open back, an adjustable ankle strap, clear criss-cross straps, an open almond toe, and an espadrille wedge heel. 

    Fit & Features

    • Open back
    • Adjustable ankle strap
    • Clear criss-cross straps 
    • Open almond toe
    • Espadrille wedge heel

    Style Number/Barcode: 07406-0273

    Category Name: Vacation Looks

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Instincts Basic Tube Dress

    Tap into your stylish instincts with a basic tube dress. The dress features a sleeveless square neckline and a midi-length silhouette. The dress is composed of a knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and a jelly purse. 

    Fit & Features

    • Sleeveless square neckline
    • Midi length silhouette
    • Knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0975

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vacay Mode Bandeau Top

    Get ready for your weekend getaway with this effortlessly chic top. It features a bandeau design with a strapless sweetheart neckline, a tie-front detail, spaghetti straps, and a cropped fit. Style this top with the matching kimono and shorts.

    Shop Matching Kimono: Vacay Mode Flowy Kimono

    Shop Matching Bottoms: Vacay Mode Flowy Shorts

    Fit & Features

    • Bandeau design
    • Strapless sweetheart neckline
    • Tie-front detail
    • Spaghetti straps
    • Cropped fit
    • Woven fabric
    • Runs true to size

    Style Number/Barcode: 06003-1423

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic And Sheer Lace Kimono

    Chic and sheer, this lace kimono is the perf lightweight layer for the summer. It features half-length kimono-style sleeves and a high-low silhouette with a flowy, relaxed fit. Style this kimono over your favorite bikini as a cute swim coverup!

    Fit & Features

    • Half-length kimono-style sleeves
    • High-low silhouette
    • Flowy, relaxed fit
    • Sheer lace fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06204-0968

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Mode Flowy Shorts

    Get ready for your weekend getaway with these effortlessly chic shorts. They feature a high-rise banded waist and a flowy, relaxed fit. Style these shorts with the matching top and kimono.

    Shop Matching Top: Vacay Mode Bandeau Top

    Shop Matching Kimono: Vacay Mode Flowy Kimono

    Fit & Features

    • High-rise banded waist
    • Flowy, relaxed fit
    • Woven fabric
    • Runs true to size

    Style Number/Barcode: 06303-0136

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Mode Flowy Kimono

    Get ready for your weekend getaway with this effortlessly chic kimono. It features three-quarter length kimono-style sleeves, an open front with a draped design, and a flowy, relaxed-fitting silhouette. Style this kimono with the matching bandeau top and shorts.

    Shop Matching Top: Vacay Mode Bandeau Top

    Shop Matching Bottoms: Vacay Mode Flowy Shorts

    Fit & Features

    • Three-quarter length kimono-style sleeves
    • Open front, draped design
    • Flowy, relaxed-fitting silhouette
    • Woven fabric
    • Runs true to size

    Style Number/Barcode: 06204-1046

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fiercely Stylish Lace-Up Leopard Maxi Dress

    Keep it fiercely stylish with a maxi dress that is part bold, part glam! The dress features a leopard print, a sleeveless square neckline with racer bust, spaghetti straps, lace-up straps at back, and a flowy A-Line silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with sandals and metal bangles. 

    Fit & Features 

    • Sleeveless square neckline
    • Spaghetti straps
    • Lace-up back 
    • A-line silhouette
    • Leopard print
    • Lightweight woven fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-1195

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free