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.

  • Desert Dreamer Crochet Lace Kimono

    Channel those dreamy boho vibes in this gorgeously detailed crochet lace kimono. The long relaxed fit is perfect for a desert music festival.

    Fit & Features

    • Sheer crochet lace fabric
    • Half-length loose sleeves
    • Open front
    • Long-length hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06204-2068

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

  • Shadow Blooms Floral Skater Dress

    Delicate and dainty, unveil this skater dress for every soiree this season! The short dress features breezy peasant long sleeves, a sweetheart neckline, a padded bust, a smocked back, and a fit and flare silhouette with a ruffled short hem. The dress is designed with a floral jacquard pattern on an airy fabric with a smooth woven lining and no stretch. Complete the look with espadrille wedges for a baby or wedding shower!

    Fit & Features

    • Peasant long sleeves, elastic cinched hems
    • Sweetheart neckline, padded bust, smocked back
    • High waist seam, fit and flare, skater silhouette
    • Short-length hem
    • Floral jacquard pattern
    • Airy fabric, smooth woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2604

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Effortless Blis Sleeveless Bodycon Knit Midi Dress

    Sit back and watch the compliments roll in when you're seen in this knit midi dress over the weekend! Crafted from a unique knit fabric offering a stretchy knit lining for comfort. It features adjustable spaghetti straps, a square neckline with a flirty bust tie, and a flattering bodycon midi-length silhouette. Complete the look in strappy sandals and a purse.

    Fit & Features

    • Unique knit fabric, stretchy knit lining
    • Adjustable spaghetti straps
    • Square neckline, bust tie
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5712

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Vacay Tropical Print Woven Romper

    Look like you're ready to jet-set off to a dreamy vacay in this bold tropical print romper! The lightweight woven fabric is accented with an abstract tropical palm leaf print with bright hues perf for sunny days by the water. The romper features a sleeveless sweetheart neckline with a dainty eyelet lace trim, a ruched bust with a tie-front detail, thin tank straps that lead to a smocked back for added stretch, a fitted high waist, and flowy shorts for a relaxed look. Style with strappy sandals!

    Fit & Features

    • Abstract tropical print
    • Woven fabric with top knit lining, eyelet lace trim
    • Sweetheart neckline, ruched bust, tie-front detail
    • Thin tank straps, stretchy smocked back, zipper with hook and eye closure
    • Fitted high waist, flowy shorts
    • Runs true to size

    Style Number/Barcode: 06403-0462

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Babe Gingham Print Side Tie Bikini Bottoms

    Channel that flirty babe style in these adorable gingham printed side tie bikini bottoms with a dainty eyelet trim. Pair with one of the matching bikini tops for a sweet and sassy look.

    Shop Matching Tops: Flirty Babe Gingham Print Triangle Bikini Top, Flirty Babe Gingham Print Bandeau Bikini Top

    Fit & Features

    • Nylon-blend fabric, high stretch
    • Gingham print
    • Eyelet trim
    • High-cut design, side tie closures
    • Cheeky fit
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-0865

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Just A Girl Mid-Rise Striped Boxer Skort

    You're just a girl who loves to look cute and casual, and this striped boxer skort is just the ticket! With a flattering mid-rise waist with button accents and a form-hugging fit, you'll love having this skort in the lineup.

    Fit & Features

    • Striped print, woven fabric
    • Elasticized mid-rise waist, button accents
    • Form-hugging fit
    • Shorts lining
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06303-000024

    Category Name: Vacation Looks

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: PINK

    Available Size: M

    Product Badge:
    • Sale
  • Fall Favorite Turtleneck Braided Sleeve Sweater

    Look no further for your new favorite turtleneck sweater this season! It features long sleeves with an eye-catching braided design, a cropped hem, and is crafted from a soft rib knit fabric perfect for keeping cozy and cute. Complete the look in a trendy pleated mini skirt for a coffee date and movie!

    Fit & Features

    • Long sleeves, braided design
    • Turtleneck
    • Cropped hem
    • Soft rib knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1751

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everyday Style Short Sleeve Ruched Mini Dress

    Level up your everyday style with this simple yet chic mini dress! The lightweight smooth nylon fabric includes a knit lining and offers plenty of stretch for ultra-comfortable wear. Shaped with a classic scoop neckline and short sleeves, the mini-length dress features ruching down the side seams to flaunt your figure on the bodycon silhouette. Pair with a denim jacket and sneakers.

    Fit & Features

    • Smooth nylon fabric with knit lining, plenty of stretch
    • Scoop neckline
    • Short sleeves
    • Ruched side seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5669

    Category Name: Vacation Looks

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • New Addiction Mid-Rise Fray Denim Shorts

    Upgrade your denim collection with these mid-rise denim shorts with a trendy frayed hem and perfect vintage-inspired look and feel!

    Fit & Features

    • Medium wash denim
    • Front button and zipper closure, belt loops
    • Five-pocket styling
    • Frayed hem
    • Runs true to size

    Style Number/Barcode: 06603-0508

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: MED, DENIM

    Available Size: S, XL

  • Charming Appeal Puff Sleeve Eyelet Knit Skater Dress

    The sweet eyelet design and adorable details give this puff sleeve skater dress a charming appeal! Made with an airy sheer eyelet knit fabric with a partial knit lining, this short dress is perfect for your spring and summer weekend outings. It features a square neckline with chic ruching at the bust, sheer short puff sleeves with a dainty ruffled trim, a sheer corset-style bodice to create a cinched look, and a fit-and-flare skater silhouette for a flirty vibe. Complete your outfit with hoop earrings!

    Fit & Features

    • Sheer eyelet knit fabric, partial knit lining, plenty of stretch
    • Square neckline with ruched bust
    • Sheer short puff sleeves, ruffled trim, elastic cinched hems
    • Sheer corset-style bodice, stretchy high waist seam
    • Fit and flare skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5427

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Stand Out Faux Leather Suede Sneakers

    Are you looking to make your casual 'fits stand out? These sneakers feature a round toe and lace-up placket for the perfect fit. The faux suede pattern adds a touch of contrast while the rubber sole provides traction. Crafted from sleek faux leather, these sneakers are a must-have! Style with a trendy denim jumpsuit for weekend plans!

    Fit & Features

    • Round toe
    • Lace-up placket
    • Faux suede contrast pattern
    • Rubber traction sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07407-0224

    Category Name: Vacation Looks

    Price: $24.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Greetings From Mallorca Graphic Tee

    A cute knit tee to pack with you on vacay! It boasts a front graphic with a script that reads "Greetings From Mallorca" and a fitted crop hem perfect for styling with high-rise bottoms.

    Fit & Features

    • Stretchy cotton-blend knit fabric
    • Crew neckline
    • Short sleeves
    • Front graphic, script reads "Greetings From Mallorca"
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-000038

    Category Name: Vacation Looks

    Price: $22.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beach Siren Energy Crochet Lace Duster

    Sunkissed, styled, and totally that girl—this crochet lace duster brings the heat wherever you go. With a flirty tie-front finished with boho-chic beads and a dreamy longline fit, it's the layer your bikini or outfit has been begging for

    Fit & Features

    • Sheer crochet lace
    • Tie-front with bead detail
    • Bell long sleeves
    • Flowy longline hem
    • Runs true to size

    Style Number/Barcode: 06202-000021

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: TAN

    Available Size: S, M, L, XL

  • Glam Squad Faux Leather Rhinestone Sneakers

    Make any outfit shine in these fashion sneakers! With a round toe, rhinestone embellished lace-up placket and tongue, a platform rubber sole, and a sleek faux leather upper, these sneakers are perfect for stepping out with your glam squad. Complete the look in a smooth knit dress to elevate your style for day or night plans!

    Fit & Features

    • Round toe
    • Rhinestone-embellished lace-up placket
    • Rhinestone embellished tongue
    • Platform rubber sole
    • Faux leather upper
    • Cushioned footbed
    • Runs true to size

    Style Number/Barcode: 07407-0218

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jetset Babe One Shoulder Tropical Maxi Dress

    Jetset off on vacation like a babe in this tropical maxi dress! With a flirty and flattering one-shoulder neckline, ruched seams, and a bodycon silhouette, you'll be turning heads. Plus, the side slit and maxi-length hem add a touch of allure. Complete the look in sandals and sunglasses.

    Fit & Features

    • Tropical palm leaf print, stretchy knit
    • One shoulder neckline
    • Bodycon silhouette
    • Side slit
    • Runs true to size

    Style Number/Barcode: 05102-5702

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Enticing Sass Halter Cutout Wide-Leg Jumpsuit

    Unlock the sass in this sleeveless knit jumpsuit featuring a sultry halter neckline, a cutout front, and a flattering wide-leg silhouette perfect for styling with sandals. The smooth knit fabric offers a comfortable stretch.

    Fit & Features

    • Smooth knit fabric, moderate stretch
    • Halter neckline, spaghetti strap tie
    • Cutout front
    • Wide-leg silhouette
    •  Jumpsuit has a 12.5” front rise with a 33” inseam
    • Runs true to size

    Style Number/Barcode: 06502-2535

    Category Name: Vacation Looks

    Price: $34.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Give Me Cozy Half-Zip Fuzzy Knit Crop Sweater

    Cozy up in this fuzzy knit sweater for warm cuddles all day and a cute look! The sweater features slouchy long sleeves with ribbed cuffs, a half-zipper front closure, a foldover collar neckline, and a cropped rib hem. Style with high-rise jeans for school or casual weekend plans!

    Fit & Features

    • Slouchy long sleeves with ribbed cuffs
    • Half-zipper front closure
    • Foldover collar neckline
    • Cropped rib hem
    • Fuzzy knit sweater fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1757

    Category Name: Vacation Looks

    Price: $3.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Flirt High Waist Ditsy Floral Ruched Mini Skirt

    Sweet and flirty, this floral ruched mini skirt will capture the soft girl trend! The lightweight knit fabric is detailed with an adorable ditsy floral print for the cutest vibes. The skirt features a high-rise elasticized waist, a ruched seam with an adjustable drawstring for a customized fit, a short front slit, and a bodycon silhouette. Style with the matching tie-front top for a day date!

    Shop Matching Top: Sweet Flirt Flutter-Sleeve Ditsy Floral Tie-Front Top

    Fit & Features

    • Ditsy floral printed knit fabric, moderate stretch
    • High-rise elasticized waist
    • Ruched seam with adjustable drawstring
    • Short slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-1005

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Boho Scallop Hem Knit Hot Shorts

    Create a boho babe vibe in these high-rise knit hot shorts with a cheeky form-hugging fit and trendy scalloped hem. Style with the matching top for festival season!

    Shop Matching Top: Feelin' Boho Halter Open Back Knit Top

    Fit & Features

    • Sweater knit fabric
    • High-rise banded waist
    • Cheeky form-hugging fit
    • Scalloped hem
    • Runs true to size

    Style Number/Barcode: 06503-1275

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Cozy Weather Faux Fur Bucket Hat

    This adorable faux fur bucket hat is a cozy must-have for your cold-weather 'fits! It features a classic bucket hat design composed of an ultra-plush faux fur material with a smooth woven lining. Style with a sherpa-lined jacket for all the comfy vibes this season!

    Fit & Features

    • Classic bucket hat design
    • Short brim
    • Faux leather material
    • Woven interior

    Style Number/Barcode: 07302-1568

    Category Name: Vacation Looks

    Price: $4.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Butterfly Effect Rimless Square Sunglasses

    Giving fairycore with a side of don’t talk to me. These rimless tinted lenses and butterfly accents are straight-up magical for brunch, beach, or bossing up.

    Fit & Features

    • Rimless square tinted lenses
    • Delicate butterfly accents on frame corners
    • Lightweight plastic arms
    • Nose support pads

    Style Number/Barcode: 07008-000014

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: PINK

    Available Size: NS

  • Cold Babe Faux Sherpa Block Heel Booties

    Strut like a babe in these cozy faux leather booties! They feature a square-shaped toe, an inner zipper closure, a platform sole, a tall block heel, and a soft faux sherpa trim to help keep you warm on chilly days. Complete the look with a cozy jacket.

    Fit & Features

    • Square toe
    • Inner zipper closure
    • Platform sole
    • Tall block heel
    • Faux sherpa trim
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1681

    Category Name: Vacation Looks

    Price: $12.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Take Me Away Tube Midi Dress

    Effortless but still a serve. This strapless knit midi hugs your curves with a twist-front neckline and scalloped hem—perfect for brunches, beach dates, or packing for your next getaway!

    Fit & Features

    • Texture knit cotton-blend fabric, moderate stretch
    • Sweetheart strapless tube neckline
    • Twist bust
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000018

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: SAGE

    Available Size: XS, S, M, L

  • Layer Up Sleeveless Puffer Vest With Pockets

    Style up your look in this puffer vest for the chilly season ahead! Featuring a sleeveless design with a standing collar neckline, front zipper closure, and an elasticized cropped hem. Crafted with an insulated nylon woven fabric and hidden side pockets with snap-button closures for extra comfort and warmth. Complete the look in a basic long sleeve top and jeans for a coffee run and errands!

    Fit & Features

    • Sleeveless standing collar neckline
    • Front zipper closure
    • Hidden side pockets with snap-button closures
    • Elasticized cropped hem
    • Insulated nylon woven fabric for warmth
    • Puffer design
    • Runs true to size

    Style Number/Barcode: 06201-0428

    Category Name: Vacation Looks

    Price: $18.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale