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.

  • Free Spirit Chick High-Rise Boho Flare Pants

    These boho pants are for the free-spirit chicks who want to look trendy during festivals, concerts, or at parties! Made from a soft brushed knit stretchy fabric with a bohemian-inspired print, they feature a flattering high-rise elasticized waist for comfort, a hip-hugging fit, and a flared hem. Style with a cute crop top!

    Fit & Features

    • Bohemian-inspired print
    • Brushed knit stretchy fabric
    • Hip-hugging fit
    • Flared hem
    • Runs true to size

    Style Number/Barcode: 06502-2459

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Inspired Art Abstract Bodycon Mini Dress

    Bring a little extra artsy glamour to any plans in this abstract bodycon mini dress sure to inspire many compliments! 

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Adjustable spaghetti straps
    • Square neckline, padded bra cups
    • Front ruched drawstring
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-5952

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Coastal Destination Halter Tie-Front Crop Top

    Go bold in this halter crop top designed to bring an alluring look with a center slit and string tie-front. Perfect for coastal vacays!

    Fit & Features

    • Texture knit fabric, bust knit lining
    • Halter plunge V-neckline, spaghetti strap tie
    • String tie-front with beaded ends
    • Center slit design
    • Crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000032

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: In Stock

    Available Color: MOCHA

    Available Size: S, M, L

  • Perfect Style Faux Leather Platform Block Heels

    These on-trend platform block heels are the perfect style for elevating your look! Designed with smooth faux leather material, they feature a chunky block heel for comfortable wear, an open almond-shaped toe with a wide criss-cross strap design, thin adjustable ankle and heel straps with a buckle closure, and a tall platform sole for that added height. Pair with a flowy sundress for a weekend party!

    Fit & Features

    • 4.5" Chunky block heel
    • Faux leather upper, padded insole
    • Open almond toe
    • Criss-cross strap design
    • Adjustable ankle and heel straps with buckle closure
    • Platform sole
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4670

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Romance Floral Lace-Up Maxi Dress

    Evoke chic romance on date night in this gorgeous floral maxi dress designed with an open lace-up strappy back and floor-length form-hugging silhouette. Style with a sleek handbag and stiletto heels.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Large floral print
    • Sleeveless deep V-neckline
    • Spaghetti straps
    • Open cross-back lace-up strappy design
    • Maxi-length hem, form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000111

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L, XL

  • Clean Lines Scoop Neck Seamless Top

    This minimalistic basic top is what every girl needs for everyday styling! The crop top features long fitted sleeves, and a scoop neck, and is composed of a buttery soft knit fabric with a seamless design. Complete the look in a cute jean jacket, paper bag pants, and booties! 

    Fit & Features

    • Long fitted sleeves
    • Scoop neck
    • Cropped hem
    • Buttery soft knit fabric, seamless design
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1534

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Luxury Cowl Neck Marble Glitter Mini Dress

    Indulge in the flirty luxury of this mesh mini dress for a night on the town! Crafted from an airy mesh fabric adorned with a glam marble print with glitter streaks, this dress is ready to be the most divine at the club. Featuring a sultry cowl neckline, adjustable spaghetti straps for a custom fit, and side ruched seams along the bodycon silhouette that flaunts your figure! Complete the look with platform heels.

    Fit & Features

    • Marble print, glitter streaks
    • Mesh fabric, sewn-in knit lining with stretch
    • Adjustable spaghetti straps
    • Side ruching
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-5432

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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 Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: MINT

    Available Size: M

    Product Badge:
    • Sale
  • Put A Ring On It Sweater Midi Dress

    A sultry take on a classic staple! This sweater midi dress features fitted long sleeves, a v-neckline, a front cutout with a ring hoop insert, and a form-hugging silhouette with a flirty front slit. Style with pointed-toe booties to complete the look!

    Fit & Features

    • Fitted long sleeves
    • V-neckline
    • Front cutout with a ring hoop insert
    • Form-hugging silhouette
    • Front slit, midi-length hem
    • Rib-knit sweater fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1612

    Category Name: Vacation Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Fab Zip-Front Denim Romper

    Trendy fab will be your vibe in this cool-girl denim romper featuring a collared neckline, zip-front design, and form-hugging fit!

    Fit & Features

    • Denim fabric, minimal stretch
    • Sleeveless collared neckline
    • Zip-front V-neckline
    • High-rise waist, belt loops
    • Single front pocket
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06603-0481

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: MEDIUM, DENIM

    Available Size: XS, S, M, L

  • Henley Formal Lace-Up Midi Dress

    Special Occasion

    Lace-up in a formal dress that brings the radiance to your evening! Henley features a sleeveless square neckline, spaghetti straps, a bold lace-up back, and a midi-length silhouette accented with a high-side slit. The dress is composed of a lined crepe fabric that offers a form-flattering fit with a moderate stretch. Complete look with rhinestone heels and a sphere clutch. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Lace-up back 
    • Midi length silhouette
    • High side slit
    • Lined crepe fabric 
    • Form-hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05001-0755

    Category Name: Vacation Looks

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Strut It Out Abstract Zebra Tie-Front Top

    Fit & Features

    • Sheer mesh fabrication
    • V-neckline
    • Tie-front bodice
    • Long sleeves
    • Zebra print
    • Cropped hem
    • Runs true to size 


    Shop Matching Skirt: Strut It Out Abstract Zebra Maxi Skirt

    Style Number/Barcode: 06202-0505

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: L

    Product Badge:
    • Part of a Set
  • Set It Off Ruffled Bodycon Dress

    Set off your night with a head-turning bodycon that raises the heat! The dress features a sleeveless wrap V-neckline, spaghetti straps, a ruched body, and a mini-length silhouette with a ruffled hem. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with rhinestone heels and a clutch. 

    Fit & Features

    • Sleeveless wrap V-neckline
    • Spaghetti straps
    • Ruched body
    • Mini length silhouette, ruffled hem 
    • Smooth knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4464

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Light Sleeveless Linen Corset Top

    Keep it light and effortless in this linen corset top for a day spent under the sun! With a sleeveless V-wired neckline and tank straps, this top offers a flattering fit. The cropped hem flaunt your figure, while the linen fabric elevates the look. Style with the matching bottoms.

    Shop Matching Bottoms: Keep It Light High Rise Linen Palazzo Pants

    Fit & Features

    • Linen woven fabric, no stretch
    • Tank straps
    • Cropped hem
    • Multiple back hook and eye fasteners
    • Runs true to size

    Style Number/Barcode: 06003-2359

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Love High-Rise Lace Trim Skort

    This high-rise skort is perfect for any fun occasion! The high waist and flowy silhouette provide a flattering fit, while the uneven lace trim hem adds a touch of charm.

    Fit & Features

    • Stretchy knit fabric
    • Folded high-rise waist
    • Flowy silhouette
    • Uneven lace trim mini-length hem
    • Shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000025

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: OFF, WHITE

    Available Size: S, M, L

  • Wild Card Knit Cutout Crop Top

    Match your wardrobe to your mood! This flirty crop top features long sleeves, a v-neck, and dual front twist accents and cutouts on brushed knit fabric with plenty of stretch. Style with high-rise jeans for happy hour!

    Fit & Features

    • Long sleeves
    • V-neck
    • Dual front twist accents and cutouts
    • Cropped hem
    • Brushed knit fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06001-4554

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Too Glam To Shade Square Rhinestone Trim Sunglasses

    These sleek square frames with rhinestone-embellished trim bring full diva energy wherever you go!

    Fit & Features

    • Rhinestone-embellished trim on arms
    • Sleek square metal frames
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000008

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: NS

  • Casual Classic Button-Front Henley Bodysuit

    This casual classic henley bodysuit will be a new wardrobe staple! It features a V-neckline, a partial faux button-front design, short sleeves, a thong bottom with a dual snap-button closure, and a form-hugging fit. The ribbed knit fabric offers plenty of stretch. Style with high-rise denim and your fave mules.

    Fit & Features

    • V-neckline
    • Partial faux button-front design
    • Short sleeves
    • Thong bottom, dual snap-button closure
    • Form-hugging fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06002-1560

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • A Sweet Look Sleeveless Ruffled Skater Dress

    A sweet skater dress for showers or brunch! With its romantic sweetheart neckline and bust tie, you'll feel so flirty. The adjustable spaghetti straps allow for a perfect fit while the ruffled skater silhouette and short-length hem add a touch of playful charm. The partially smocked back offers added stretch. Complete the look with a heart necklace and sandals.

    Fit & Features

    • Gauze woven fabric with stretchy knit lining
    • Sweetheart neckline, bust tie
    • Adjustable spaghetti straps
    • Stretchy smocked back
    • Ruffled skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5499

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Fun High Rise Striped Knit Midi Skirt

    Give your vacay style a dynamic upgrade in this flirty knit midi skirt perfect for a getaway or weekend fun! The skirt boasts a high-rise waist, a bodycon fit, a center back slit for movement, and a midi-length hem on pointelle knit fabric showcasing a trendy striped pattern. Complete the look with the matching top.

    Shop Matching Top: Flirty Fun V-Neck Tie Striped Knit Crop Top

    Fit & Features

    • Pointelle knit fabric, striped pattern
    • High-rise waist
    • Center back slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-1013

    Category Name: Vacation Looks

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunkissed and Snatched Halter Midi Dress

    Serving body, legs, and “where’d you get that?” energy. This halter midi dress hugs every curve in a flattering bodycon fit while the cutouts do all the flirting! Pair with cute sandals or mules.

    Fit & Features

    • Stretchy knit fabric
    • Halter neckline with tie straps
    • Side cutouts
    • Side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000022

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS, S, M, L

  • Whimsical Muse Chiffon Swiss Dot Skater Dress

    You'll be a chic whimsical muse in this airy chiffon skater dress! The short dress features a square neckline, short billowy puff sleeves with ruffled accents at the shoulders, an open back with an adorable bow tie-back design, and a short skater skirt with a flared-out silhouette. The lined chiffon fabric features an all-over swiss dot pattern. Style this flirty dress with classic block heels.

    Fit & Features

    • Square neckline
    • Short puff sleeves, ruffled accents, elasticized hems
    • Open-back, bow design, tie closure
    • Empire waist, elastic back
    • Short skater skirt, fit and flare silhouette
    • Sheer chiffon fabric, swiss dot pattern, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2288

    Category Name: Vacation Looks

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Follow Your Heart Sleeveless Ruffled Lace Maxi Dress

    Follow your heart and it'll lead you to this lace maxi dress! Perfect for bridal showers, dressy brunches, or parties. This sleeveless dress brings an allure of romance in a square neckline with adjustable spaghetti straps, a stretchy smocked bodice, and a tiered ruffled silhouette. Complete the look in strappy heeled sandals.

    Fit & Features

    • Lace fabric, stretchy knit lining
    • Adjustable spaghetti straps
    • Square neckline
    • Tiered ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3382

    Category Name: Vacation Looks

    Price: $28.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' The Heat Halter Crop Top

    Vacation or staycation, this halter crop top turns up the heat anywhere you go! 

    Fit & Features

    • Slinky knit stretchy fabric
    • Halter neckline with decor insert
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000056

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: WHITE, RUST

    Available Size: M, L, S

    Product Badge:
    • Best Seller