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.

  • Total Keep Crepe Tie-Front Top

    Dress up your outfit by layering on this crepe top featuring short sleeves and a tie-front closure along the cropped hem. Style with a basic cami and jeans.

    Fit & Features

    • Short sleeves
    • Tie-front closure
    • Cropped hem
    • Crepe fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06204-1386

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Getaway Sheer Mesh Duster

    Layer on this airy sheer mesh duster to look like you're ready for an island getaway! It features long fitted sleeves, an open front, a long, flowy silhouette, and an all-over palm leaf print. Style over your fave bikini as a chic cover-up.

    Fit & Features

    • Long fitted sleeves
    • Open front
    • Long flowy silhouette, relaxed fit
    • Palm leaf print
    • Sheer mesh fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06202-0302

    Category Name: Vacation Looks

    Price: $11.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Seasonal Striped Pleat Shorts

    Refresh your closet for summer! Show off your flirty style in these striped shorts featuring a high-rise waist, form-fitting silhouette, and pleated lined fabric. Complete the look in the matching top.

    Shop Matching Top: Seasonal Striped Pleat Tank Top

    Fit & Features

    • High-rise waist
    • Form-fitting
    • Striped pattern
    • Pleated lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06503-0700

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Seasonal Striped Pleat Tank Top

    Refresh your closet for summer! Show off your flirty style in this striped tank top featuring a sleeveless, sweetheart neckline, adjustable spaghetti straps, and a front twist accent on the cropped hem. Complete the look in the matching shorts.

    Shop Matching Shorts: Seasonal Striped Pleat Shorts

    Fit & Features

    • Sleeveless, sweetheart neckline, adjustable spaghetti straps
    • Front twist accent
    • Cropped hem
    • Striped pattern
    • Pleated lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06001-3987

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Beauty Tropical Print Halter Top

    Show off your beauty on your next vacay in this sleek knit halter top with a trendy O-ring bust accent and an alluring tropical palm leaf print.

    Fit & Features

    • Smooth knit fabric, high stretch
    • Tropical palm leaf print
    • Sleeveless V-neckline, bust O-ring accent
    • Halter strap
    • Partially open back
    • Fitted mid-length hem
    • Runs true to size

    Style Number/Barcode: 06001-000089

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Stroll Woven Slide Sandals

    Take the perfect summertime stroll in these chic woven slides! The sandals feature a rounded toe, a wide toe strap, a flat sole, and a woven raffia material. Style with a sleek pair of sunglasses.

    Fit & Features

    • Rounded toe
    • Wide toe strap
    • Flat sole
    • Woven raffia material
    • Runs true to size

    Style Number/Barcode: 07404-0980

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Mood Ombre Aviator Sunglasses

    Showcase major trendy vibes in these sleek aviator sunglasses! They feature a thin metal frame with mirrored ombre lenses. Style with a mini dress and boots for the cutest summer 'fit!

    Fit & Features

    • Aviator design
    • Thin metal frame
    • Mirrored ombre lenses
    • Rubber nose supports
    • UV 400 protection

    Style Number/Barcode: 07008-0973

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Give Me Glam Oversized Sunglasses

    You're all about that glam life. These oversized shades are a must-have for you! The sunglasses feature square-shaped tinted lenses, a plastic frame, metal side trims, and thin metal arms. Style with a chic crossbody purse.

    Fit & Features

    • Oversized design
    • Square-shaped tinted lenses
    • Plastic frame
    • Metal side trims
    • Thin metal arms
    • 100% UV protection

    Style Number/Barcode: 07008-0976

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Festive Babe Crochet Fringe Top

    Get ready for festival season babe! This boho crochet fringe top features a sleeveless, halter neck with tie closure, open-back, and a cropped length. Complete the look in distressed denim shorts and a ring set.

    Fit & Features

    • Sleeveless, halter neck with tie closure
    • Open-back
    • Cropped length
    • Crochet design with fringe
    • No stretch
    • Fits true to size

    Style Number/Barcode: 06005-1307

    Category Name: Vacation Looks

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dance All Day Crochet Halter Top

    Get ready to dance at every festival looking so fire in this crochet halter top featuring a trendy open-back with tie closure and a v-neck atop an ultra cropped hem. Complete the look in boho-flared pants.

    Fit & Features

    • Sleeveless, halter v-neck, tie closure
    • Open-back
    • Crochet design, unlined
    • Fits true to size, no stretch

    Style Number/Barcode: 06005-1401

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Everyday Trendsetter Cutout Crop Top

    Showcase major trendsetter status in this chic crop top that is perf for every day. It features a sleeveless racer neckline, an asymmetrical cutout above the bust, and a cropped, form-hugging fit. Style with a mini skirt and mules.

    Fit & Features

    • Sleeveless racer neckline
    • Asymmetrical cutout above the bust
    • Cropped, form-hugging fit
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4206

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • One Hit Wonder Surplice Tie Jumpsuit

    This sleeveless jumpsuit will be a hit everywhere you go! It features a collared v-neck, adjustable spaghetti straps, a surplice bodice, and a tie-waist on a straight-leg silhouette. Composed of woven fabric with a minimal stretch. Finish the look in lattice booties.

    Fit & Features

    • Sleeveless, collared v-neck, adjustable spaghetti straps
    • Back zipper closure
    • Surplice bodice
    • Tie-waist, straight-leg design
    • Woven fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 06402-0402

    Category Name: Vacation Looks

    Price: $6.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Skip A Beat Criss Cross Halter Top

    Your heart will skip a beat for this halter top! Featuring a sleeveless, criss-cross strap bodice with a keyhole accent, fitted crop hem, and an open-back design on stretchy rib-knit fabric. Complete the look in boyfriend jeans.

    Fit & Features

    • Sleeveless, halter neckline
    • Criss-cross straps
    • Keyhole accent
    • Fitted crop hem
    • Open-back design
    • Stretchy rib-knit fabric
    • Runs true to size

    Style Number/Barcode: 06001-4208

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • May Blooms Lace-Up Midi Dress

    May flowers are blooming on this sultry midi dress featuring a sleeveless, cowl neck, spaghetti straps that lace up on the open back, a form-hugging fit, and a side slit accent. Complete the look in simple block heels for a daytime event.

    Fit & Features

    • Sleeveless, cowl neck, spaghetti straps
    • Open-back, lace-up design
    • Form-hugging fit
    • Side slit accent
    • Midi-length hem
    • Slinky knit fabric, moderate stretch. fits true to size

    Style Number/Barcode: 05101-1625

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Remy High Rise Fray Denim Shorts By Windsor Denim

    Don't get stressed cause you'll be well dressed in the Remy high-rise denim shorts by Windsor Denim! Your curves will be blessed in these jean shorts featuring a flattering, high-rise waist, distressed accents, figure-flattering design, and a frayed cutoff hem on a medium wash denim fabric with a vintage-inspired color fade effect. Complete the look in a cute crochet crop top for a music concert.

    Fit & Features

    • High-rise waist
    • Distressed accents, frayed cutoff hem
    • Figure-flattering design
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Medium wash denim, color fade effect, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06603-0240

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Good Times Flow Tulip Pants

    Make many memories in these tulip pants featuring a high-rise elasticized waist, front partial slits that run from top to bottom, and a flowy wide-leg silhouette on woven fabric. Complete the look in a boho crop top and sandals for a trendy summer night dinner.

    Fit & Features

    • High-rise elasticized waist
    • Front partial slits that run top to bottom
    • Flowy wide-leg silhouette
    • Back zipper closure
    • Woven fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06302-0659

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Palms Strapless Jumpsuit

    The palms on this breezy jumpsuit are a total summer vibe! It features a strapless, sweetheart neck, a knot accented bust, elasticized lattice straps on the open back, a cutout bodice, and a wide-leg silhouette. Complete the look in sandals for a vacation fit.

    Fit & Features

    • Strapless, sweetheart neck
    • Elasticized lattice straps on the open back
    • Knot accented bust, cutout bodice
    • Wide-leg silhouette
    • Palm print, gauze woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0618

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Paper Bag Of Tricks Denim Cuff Shorts

    These denim shorts are such a treat with no tricks! They feature a cute, paper bag high-rise waist, roll cuffed hem, dual button front, hidden zipper closure, belt loop accents, and a classic 5-pocket design. Complete the look in a bodysuit and sandals.

    Fit & Features

    • Paper bag high-rise waist
    • Roll cuffed hem
    • Dual button front and hidden zipper closure
    • Belt loop accents
    • Classic 5-pocket design
    • Non-stretch denim fabric
    • Fits true to size

    Style Number/Barcode: 06603-0265

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Strut It Out Abstract Zebra Maxi Skirt

    Perfect your vibe with the strut it out abstract zebra maxi skirt. This sheer mesh beauty flaunts a zebra print and mid-rise waist for a fierce look. Pair it with the matching top for ultimate style.

    Fit & Features

    • Sheer mesh fabrication lined with stretchy knit
    • Mid-rise waist
    • Zebra print
    • Maxi length hem
    • Runs true to size


    Shop Matching Top: Strut It Out Abstract Zebra Tie-Front Top

    Style Number/Barcode: 06501-1105

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Boho Bliss Crochet Lace Crop Top

    The cute crochet lace detailing of this crop top makes it so boho-chic! The top features a sleeveless V-neckline, adjustable spaghetti straps, a floral crochet lace design, and a cropped fit with a scalloped trim. Style with printed flare pants and espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Floral crochet lace design
    • Partially smocked back
    • Cropped fit, scalloped trim
    • Woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-1791

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tropical Glam Ruched Short Dress

    Keep it glam on your tropical getaway with a mini dress that brings those island vibes! The dress features a tropical floral print, a sleeveless square neckline, spaghetti straps, ruching, and a short length with a rounded hem. The dress is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and a straw hat

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching
    • Tropical floral print
    • Short length hem
    • Lined smooth knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4683

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Standout In Glam Thong Wedge Sandals

    Stand out in these glam sandals while soaking up the sun! They feature a round toe, clear stone embellished thong strap, wedge sole, and a comfort foam footbed. Complete the look in a chic swimsuit and wrap.

    Fit & Features

    • Round toe
    • Clear stone embellished thong strap
    • Wedge sole
    • Comfort foam footbed
    • Slide-on/off styling
    • Runs true to size

    Style Number/Barcode: 07404-1012

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Silky Chic Kimono Tie-Front Top

    Silky and so chic! Luxe up your look in this satin crop top featuring three-quarter-length kimono sleeves, a plunge V-neckline, a tie-front closure, and a cropped hem. Complete the look in trouser shorts and sandals for vacation.

    Fit & Features

    • Three-quarter-length kimono sleeves
    • Plunge V-neckline
    • Tie-front closure
    • Cropped hem
    • Silky satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1298

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Tide Halter Cutout Midi Dress

    Flaunt this midi dress on your island getaway! Designed to accentuate your fab figure on a sleeveless, halter neck with tie closure, and sultry side cutouts on the form-fitting silhouette. Complete the look in strappy mules for a sunset dinner.

    Fit & Features

    • Sleeveless, halter neck, tie closure
    • Side cutouts
    • Partial open-back design
    • Form-fitting silhouette
    • Midi-length hem
    • Sweater-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1313

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance