Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • Weekend Date Lace-Up Espadrille Wedges

    These lace-up espadrille wedges will make a cute finishing touch for your date this weekend! 

    Fit & Features

    • Wedge heel
    • Almond toe with crisscross straps
    • Lace-up ankle straps
    • Espadrille material
    • Runs true to size

    Style Number/Barcode: 07406-000001

    Category Name: Vacation Looks

    Price: $30.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 6, 7.5

  • Vacation Queen High-Rise Slit Tropical Maxi Skirt

    Unleash your inner vacation queen with this tropical maxi skirt! Made from stretchy knit fabric, this skirt is perfect for any tropical adventure with its eye-catching palm print. Its high-rise waist and flowy silhouette will flatter your figure, while the high front slit adds a touch of sass. Complete the look with sandals.

    Fit & Features

    • Tropical palm print, stretchy knit fabric, bikini brief lining
    • High rise waist
    • High front slit
    • Flowy silhouette
    • Runs true to size

    Style Number/Barcode: 06501-0967

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Playful Distraction Low Rise Ruffled Mini Skirt

    Be a playful distraction in this low-rise mini skirt this summer! Crafted from jacquard pattern woven fabric, it's the perfect way to make a stylish statement with a touch of whimsy. Features a low-rise waist paired with a tiered ruffled silhouette creating a flirty mini-length hem. Complete the look in a crop top and platform sneakers!

    Fit & Features

    • Jacquard pattern, woven fabric lined with stretchy knit
    • Low rise waist
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 06401-0674

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All-Day Slay Oversized Cat-Eye Sunglasses

    Show off an all-day slay in these sleek cat-eye sunglasses! They feature an oversized cat-eye design with a thin metal frame, sassy leopard-printed arms, and tinted lenses. Style these chic shades with hoop earrings.

    Fit & Features

    • Oversized cat-eye design
    • Thin metal frame
    • Leopard-printed arms
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1066

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • City In Style Rhinestone Trim Sunglasses

    Stroll the city in these stylish sunglasses for a trendy allure. They feature tinted lenses with rhinestone trim for a hint of glam, rubber nose supports, and a comfortable fit. Complete the look in a basic midi dress for shopping and grabbing coffee!

    Fit & Features

    • Tinted lenses with rhinestone trim
    • Rubber nose supports
    • Comfortable fit
    • 100% UV protection

    Style Number/Barcode: 07008-1079

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Magic Of Memories Abstract Halter Crop Top

    Create fabulous memories in this crop top for any occasion! With a daring plunge halter neckline and gorgeous abstract print, you'll turn heads everywhere you go.

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Plunge halter neckline
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000147

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: PINK

    Available Size: S, M, L

    Product Badge:
    • Best Seller
  • Sunshine Babe Ditsy Floral Cropped Tube Top

    Radiate sunny vibes in the cutest cropped tube top! Designed with an adorable ditsy floral print on stretchy smocked knit fabric, it features a strapless straight-across neckline, a cropped hem, a dainty ruffled trim, and a form-hugging fit. Style with denim shorts and sneakers.

    Fit & Features

    • Ditsy floral print
    • Stretchy smocked ribbed knit fabric
    • Strapless straight neckline
    • Cropped hem
    • Ruffled trims
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06002-1901

    Category Name: Vacation Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In My Feels High-Rise Midi Skirt

    Whether you're on vacay or sitting poolside, this high-rise midi skirt will have you feeling yourself! Pair with the matching top.

    Fit & Features

    • Stretchy knit fabric
    • High-rise waist
    • Column silhouette
    • Midi-length hem
    • Runs true to size

     

    Shop The Matching Top: In My Feels Scoop Neck Bra Top

    Style Number/Barcode: 06501-1138

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Living In The Palms Wide Leg Palazzo Pants

    Escape to a tropical island in these breezy palm print palazzo pants perfect for dinners with a view or exploring with a cocktail in hand! These pants have a flattering high-rise elastic waistband and wide-leg silhouette for style and comfort on stretchy knit palm print fabric. Complete the look with the matching top.

    Shop Matching Top: Living In The Palms Tie-Front Crop Top

    Fit & Features

    • Palm print, stretchy knit fabric
    • High-rise elastic waistband
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2462

    Category Name: Vacation Looks

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Crushin' On You Lace Trim Babydoll Floral Crop Top

    Look and feel like a precious flirt in this babydoll crop top! Made from an airy mesh fabric with an adorable floral print, this top features a delicate lace trim V-neckline, spaghetti straps, and a layered ruffled crop hem. Complete the look in denim shorts and sandals for casual plans!

    Fit & Features

    • Floral print, mesh fabric, bust lining
    • Spagehtti straps
    • Lace trim V-neckline
    • Layered ruffled crop hem
    • Runs true to size

    Style Number/Barcode: 06001-5413

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Glow-Up Watercolor Woven Tube Top

    Show off a summer glow-up in this watercolor-printed woven tube top designed with a strapless sweetheart neckline, tie-front, and fitted ultra-cropped hem. Style with the matching shorts for a chic vibe.

    Shop Matching Bottoms: Summer Glow-Up Watercolor Woven Shorts

    Fit & Features

    • Linen-like woven fabric, watercolor print
    • Strapless sweetheart neckline
    • Tie-front design
    • Stretchy smocked back
    • Fitted ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-000034

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • On The Prowl High Rise Zebra Maxi Skirt

    On the prowl and ready to unleash fierceness in this zebra print maxi skirt! It features a flattering high-rise waist with an elastic banded back for added stretch, a high front slit to show some leg, and a flowy maxi silhouette. Complete the look with the matching top.

    Shop Matching Top: On The Prowl Strapless Zebra Crop Top

    Fit & Features

    • Zebra print, woven fabric
    • High-rise waist with elastic banded back
    • High front slit
    • Flowy maxi silhouette
    • Runs true to size

    Style Number/Barcode: 06301-0191

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Looks V-Neck Lace Babydoll Dress

    Sweeten any occasion in this lace babydoll dress with a charming ruffled silhouette and mini-length hem!

    Fit & Features

    • Lace fabric, stretchy knit lining
    • V-neckline
    • Adjustable spaghetti straps
    • Ruffled babydoll silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000093

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: L

  • Laid Back Cutie High-Rise Wide-Leg Pants

    Unleash your inner laid back cutie with these high-rise wide-leg pants. The drawstring waist and side pockets provide comfort and convenience, while the flowy gauze woven fabric adds a touch of bohemian charm. Complete the look in a basic crop top for casual plans or travel!

    Fit & Features

    • Gauze woven fabric, no stretch
    • High rise drawstring waist
    • Side pockets
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06302-0813

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Oh So Sweet Tie Back A-Line Mini Dress

    You're going to look so sweet in this A-line mini dress for weekend plans! Featuring cap sleeves, a square neckline, and a tie-back design to turn heads. The A-line silhouette and mini-length hem will have you looking effortlessly chic! Complete the look in platform shoes.

    Fit & Features

    • Smooth knit fabric lined with stretchy knit
    • Square neckline
    • Tie back design
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5682

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 90s Icon Platform Block Heel Mules

    Strut like a '90s icon in these statement mules designed with a platform sole and block heel to elevate your favorite looks!

    Fit & Features

    • Block heel
    • Square toe
    • Wide foot strap
    • Platform sole
    • Jelly material
    • Runs true to size

    Style Number/Barcode: 07401-000274

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: BLACK, GOLD

    Available Size: 10, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9

  • Alluring 'Fit Plunging Halter Mini Dress

    Create an alluring 'fit for sunset drinks in this textured knit mini dress featuring a plunging V-neck with a bust tie accent, halter straps, and a bold open back with a tie-back design. The short, bodycon silhouette will flaunt your gorgeous curves.

    Fit & Features

    • Sheer textured knit fabric with knit lining, high stretch
    • Sleeveless plunging V-neckline, bust tie accent
    • Tie-back halter spaghetti straps
    • Open back, tie-back spaghetti straps
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000020

    Category Name: Vacation Looks

    Price: $29.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cabana Honey Tie Front Crochet Crop Sweater

    Head to the cabana in this stylish crochet crop sweater perfect for layering over your swimsuit! Featuring long sleeves with flare cuffs for added trendiness, dual tie-front closures, and a cropped hem that flaunts your figure. Complete the look with sunnies.

    Fit & Features

    • Sheer crochet fabric, no stretch
    • Dual tie-front closures
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-1743

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Dream Crochet Espadrille Platform Sandals

    These boho crochet espadrille platform sandals are a summer dream! They feature an open square-shaped toe, double-banded straps with a cute multi-colored crochet design, an open back for effortless on-and-off styling, and a tall espadrille platform sole and wide block heel. Style with a flowy sundress.

    Fit & Features

    • 4" Wide block heel
    • Espadrille material, faux leather upper
    • Open square toe
    • Double-banded straps, multi-colored crochet design
    • Open back, on-and-off styling
    • Platform sole
    • Luxe fit cushion insole
    • Runs true to size

    Style Number/Barcode: 07401-4721

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Best In Style Halter Button Up Vest

    You'll be voted best in style wearing this sleeveless vest perfect for weekend getaways or brunch with the ladies! The vest boasts a chic halter neckline, a partially open back to reveal some skin, button front closures, and a cropped hem to flaunt your cute self. Complete the look in trouser pants and mules for an effortless flair.

    Fit & Features

    • Twill cotton woven fabric, no stretch
    • Halter strap with button closures
    • Button front closures
    • Faux pockets
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-1715

    Category Name: Vacation Looks

    Price: $15.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dose Of Sweetness Bodycon Floral Mini Dress

    Ditsy florals add sweetness to this bodycon mini dress you'll adore for casual summer plans! Designed with a sheer eyelet knit fabric with a knit lining, this dress offers plenty of stretch for comfortable wear. It features adjustable spaghetti straps, a sleeveless square neckline with a dainty lace trim, ruching at the bust accented with a mini flower detail, and a flattering bodycon fit with a mini-length hem. Complete the look with earrings and sneakers.

    Fit & Features

    • Ditsy floral print
    • Sheer eyelet knit fabric with knit lining, plenty of stretch
    • Adjustable spaghetti straps
    • Square neckline, dainty lace trim
    • Ruched bust with mini flower detail
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5730

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island It Girl One-Shoulder Cutout Maxi Dress

    Giving tropical baddie with a side of luxury, this one-shoulder maxi brings the heat with a bold leaf print, cutout waist, and gold hardware that says, "I didn’t come to play." It's made for vacation slays, beach weddings, or poolside parties!

    Fit & Features

    • Tropical leaf print, smooth stretchy knit fabric, short lining
    • One-shoulder neckline with hardware trim
    • Side cutout bodice
    • High side slit
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000082

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Marvelous Darling Lace-Up Floral Chiffon Dress

    This floral chiffon dress is a must-have for any fashionista attending many events this season! With a floral print and ruffled hem, this fit-and-flare dress is both charming and chic. The V-neckline and ruffled straps add a touch of flirty femininity, while the open lace-up back will have everyone love swept, and is finished with a ruffled short-length hem. Complete the look with a ring set and mules!

    Fit & Features

    • Floral print, chiffon fabric lined with stretchy knit
    • Ruffled straps
    • Lace-up, back zipper and hook-eye closure
    • Fit and flare silhouette
    • Ruffled short-length hem
    • Sticky bra or pasties recommended
    • Runs true to size

    Style Number/Barcode: 05101-2962

    Category Name: Vacation Looks

    Price: $6.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ready To Charm Halter Cutout Wide-Leg Jumpsuit

    This sleeveless jumpsuit is ready to charm everyone this season! This jumpsuit features a halter neckline with a tie and strappy cutout back. The wide-leg silhouette adds a touch of breezy style to your look perfect for any occasion! Complete the look in heeled sandals.

    Fit & Features

    • Sheer woven fabric with woven lining, no stretch
    • Halter neckline with tie
    • Strappy cutout back
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06402-1415

    Category Name: Vacation Looks

    Price: $11.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale