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.

  • Nautical Vibes Striped Ribbed Knit Cropped Tank Top

    Show off trendy nautical vibes this season in this casual striped knit tank top! Made with an ultra-stretchy ribbed knit fabric, the crop top features a sleeveless notched V-neckline, thin tank shoulder straps, and a form-hugging fit for a snatched look. Style with high-rise jean shorts and sneakers for your laid-back weekend plans.

    Fit & Features

    • Stretchy ribbed knit fabric
    • Notched V-neckline
    • Tank straps
    • Cropped
    • Fitted
    • Runs true to size

    Style Number/Barcode: 07109-0383

    Category Name: Vacation Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

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  • Breezy Vibes Boho Print Knit Flare Pants

    Channel those effortless and breezy vibes in these boho print knit flare pants perf for festival season. The soft and stretchy brushed knit fabric features a trendy bohemian-inspired multi-print pattern for an eye-catching look. The high waist has a V-front design to create that snatched silhouette, with a back elastic band for comfortable wear. The hip-hugging fit continues through the leg, leading to a flared hem. Complete your outfit with a crochet top and strappy sandals!

    Fit & Features

    • Stretchy brushed knit fabric
    • Bohemian multi-print pattern
    • High waist with V-front design
    • Back elastic band
    • Hip-hugging fit
    • Flared leg
    • Runs true to size

    Style Number/Barcode: 06502-2440

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Chic Season Ruffled Wrap-Front Woven Romper

    Create a chic vibe for your summer plans in this ruffled wrap-front romper! Designed with a lightweight woven fabric, it features a surplice V-neckline with a flirty ruffled trim, adjustable spaghetti straps for a customized fit, and a secure back zipper closure. The high waist is accented with a chic wrap-front overlay with a tie-front design and an envelope hem, layered over fitted shorts. Complete the look with strappy sandals for a weekend getaway.

    Fit & Features

    • Woven fabric with no stretch, lining
    • Surplice V-neckline with ruffled trim, hook and eye closure
    • Adjustable spaghetti straps
    • Hidden back zipper with hook and eye closure
    • Wrap-front overlay, tie-front, envelope hem
    • Fitted shorts
    • Runs true to size

    Style Number/Barcode: 06403-0542

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Feeling Good Criss Cross Faux Leather Flat Sandals

    Slip on these flat sandals you'll be feeling good and looking stylish! The round-toe design and micro suede footbed offer all-day comfort, while the crisscross faux leather straps add a touch of chic to any look. Complete the look with a crossbody bag.

    Fit & Features

    • Round toe
    • Crisscross faux leather straps
    • Flat sole
    • Micro suede footbed
    • Runs true to size

    Style Number/Barcode: 07404-1178

    Category Name: Vacation Looks

    Price: $12.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Effortlessly Stylish Linen Dress

    You'll look effortlessly stylish this season in this lightweight and flowy linen dress! Designed with a breezy woven fabric, this short dress is perfect for your summer parties. The bodice is shaped with a square neckline with ruching at the bust and long balloon sleeves. The fitted waistband creates a cinched silhouette, flowing out to a short ruffled hem with an A-line fit for a pretty flair. Complete the look with clear heels.

    Fit & Features

    • Linen woven fabric, no stretch
    • Square neckline, ruched bust
    • Long balloon sleeves, elastic cinched hems
    • Front waistband, back zipper closure
    • Ruffled hem
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-4246

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Instant Classic Aviator Sunglasses

    These sleek aviator sunglasses will be an instant classic and staple for the season! They feature a traditional aviator design with tinted lenses, a thin metal frame with thin arms, a brow bar and nose bridge, and rubber nose pads for support. Style these sunnies with a denim jacket for that casual-cool vibe.

    Fit & Features

    • Aviator design
    • Tinted lenses
    • Thin metal frame and arms
    • Thin brow bar and nose bridge
    • Rubber nose pads

    Style Number/Barcode: 07008-1046

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek Icon Oversized Cat-Eye Sunglasses

    Elevate your trendy looks with these sleek cat-eye sunnies! The sunglasses feature an oversized cat-eye design, a thin metal frame and nose bridge, plastic arms, rubber nose pads, and tinted lenses. Style with strappy sandals.

    Fit & Features

    • Oversized cat-eye design
    • Thin metal frame and nose bridge
    • Plastic arms
    • Rubber nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1069

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Bold Flair Oversized Square Sunglasses

    These chic oversized sunnies will add that bold flair to your fave looks! The sunglasses feature an oversized square-shaped design, a thin metal frame and nose bridge, sleek side accents, thin metal arms, rubber nose pads, and tinted lenses. Style with chunky hoop earrings.

    Fit & Features

    • Oversized square-shaped design
    • Thin metal frame and nose bridge
    • Side accents
    • Thin metal arms
    • Rubber nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1068

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ready Set Chic Oversized Square Sunglasses

    Amp up the chic vibes of your looks with these oversized shades! The sunglasses feature an oversized square-shaped design, a thin metal frame, sleek chain-link designed arms, rubber nose pads, and tinted lenses. Style with hoop earrings.

    Fit & Features

    • Oversized square-shaped design
    • Thin metal frame and nose bridge
    • Chain-link designed arms
    • Rubber nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1064

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Chic Drama Oversized Square Sunglasses

    These fabulous oversized square sunglasses will bring the chic drama and level up your looks! They feature an oversized angled square-shaped design, a plastic frame and arms with sleek metal accents at each side, built-in nose pads, and tinted lenses. Style with a chain necklace.

    Fit & Features

    • Oversized angled design
    • Plastic frame and arms
    • Metal accents
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1063

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • So 2000s Square-Shaped Sunglasses

    Bring that early 2000s energy to your everyday looks with these trendy sunnies! The sunglasses feature a Y2K-inspired square-shaped design, a thin metal nose bridge, thin metal arms with a sleek cutout design, rubber nose pads, and tinted lenses. Style with a mini handbag.

    Fit & Features

    • Square-shaped design
    • Metal nose bridge
    • Cutout metal arms
    • Rubber nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1062

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Shady Baby Oval Sunglasses

    Serving throwback attitude with a modern twist—these cat eye sunglasses are the ultimate finishing touch to any 'fit. Whether it’s brunch, beach, or just a vibe check, they’ll have you looking instantly cooler.

    Fit & Features

    • Oval round design
    • Plastic frame
    • Gradient-tinted lenses
    • Polycarbonate
    • Blocks 100% UV

    Style Number/Barcode: 07008-000039

    Category Name: Vacation Looks

    Price: $2.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Clear Intentions Crossbody Bag With Straw Pouch

    Keep your style in the clear with this crossbody bag with a convenient straw pouch! Perfect for any occasion, this bag features a chain crossbody shoulder strap, a top flap with turn lock closure, and a straw zipper pouch for keeping extra essentials in. Complete the look with sandals.

    Fit & Features

    • Clear crossbody bag
    • Chain crossbody shoulder strap
    • Front flap with turn-lock closure
    • Straw zipper pouch

    Style Number/Barcode: 07203-1978

    Category Name: Vacation Looks

    Price: $12.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Contemporary Cutie Clear Cork High Heel Sandals

    Contemporary and cute, these high heel sandals are a fresh find for all of your upcoming spring-to-summer occasions! Features a comfortable almond toe and a clear PVC band, adding a touch of modern style. The block heel provides stability and a subtle boost, a lightly cushioned insole ensures all-day comfort, while the cork material offers a chic finish. Complete the look with a trendy crossbody bag.

    Fit & Features

    • 4" Block heel
    • Almond toe
    • Clear PVC band
    • Lightly cushioned insole
    • Cork material
    • Runs true to size

    Style Number/Barcode: 07401-4831

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Factor Oversized Square-Shaped Sunglasses

    Amp up the sleek factor of your 'fits with these fab oversized shades! The sunglasses feature a trendy oversized square-shaped design with a thin metal frame, thin metal arms, sleek cutout accents at each side, and tinted lenses. Style with hoop earrings and a chain necklace.

    Fit & Features

    • Oversized square-shaped design
    • Thin metal frame, thin metal arms
    • Rubber nose pads
    • Cutout sides
    • Tinted lenses

    Style Number/Barcode: 07008-1067

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Kiss And Shell Crochet Belt

    You'll fall for this crochet belt's beachy vibes to go with your weekend or vacation attire! The belt features round shells connected by crochet strings and has a self-tie closure. Complete the look in a tropical dress for your next escape.

    Fit & Features

    • Crochet belt
    • Round shell decorations
    • Self-tie closure

    Style Number/Barcode: 07301-1116

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Bon Voyage Sweetheart Floral Chiffon Skater Dress

    Say bon voyage looking darling in this floral chiffon skater dress whether you're heading out on your honeymoon or a trip abroad! Made from an airy chiffon fabric showcasing an adorable ditsy floral print that will make you stand out in the crowd. The sweetheart neckline and bust tie add a touch of romance while the skater silhouette and ruffled hem give it a playful twist. Complete the look with luxe earrings.

    Fit & Features

    • Ditsy floral print, chiffon fabric, stretchy knit lining
    • Adjustable spaghetti straps
    • Sweetheart neckline
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5714

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Desert Wanderer Wrap Waist Boho Flare Pants

    Escape in these boho pants to the desert for festivals or concerts! Dance the weekend away in these pants featuring a flattering wrap style high-rise waist, a hip-hugging fit, and a trendy flared hem on ultra-soft brushed knit fabric with a unique bohemian print. Complete the look in a graphic tee and cowboy hat!

    Fit & Features

    • Bohemian print
    • Brushed knit fabric, moderate stretch
    • High-rise wrap style waist
    • Hip-hugging, flared hem
    • Runs true to size

    Style Number/Barcode: 06502-2458

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Pretty Ombre Butterfly Two-Piece Hair Clips

    Look as pretty as the sunset taming your tresses with this hair clip set featuring gorgeous ombre organza butterfly clips with pretty rhinestone embellished trim. Complete the look in lace-up sandals for any occasion!

    Fit & Features

    • Two-piece hair clip set
    • Ombre organza butterflies 
    • Rhinestone embellished trim
    • Metal clip

    Style Number/Barcode: 07006-0489

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweeten The Deal V-Neck Floral Chiffon Skater Dress

    Sweeten the deal for upcoming plans showing up in this floral chiffon skater dress for brunch, birthdays, or shower celebrations! Featuring a V-neckline, adjustable straps, and a waist tie to show off your figure, a layered ruffled short-length hem adds a playful touch to the floral printed chiffon fabric. Complete the look in sandals.

    Fit & Features

    • Floral print, chiffon fabric, woven lining
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Ruffles
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3222

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Imagination Square Neck Eyelet Floral Bodysuit

    All of your outfits will be adorable when you style them with this floral bodysuit! Crafted from an eyelet floral printed knit fabric, this sleeveless bodysuit boasts a square neckline adorned with shoulder straps and a form-hugging fit. Complete the look with trendy distressed jeans and your favorite sneakers.

    Fit & Features

    • Eyelet knit fabric, floral print, sewn-in knit lining, stretchy
    • Shoulder straps
    • Form-hugging fit
    • Thong bottom, dual snap-button closures
    • Runs true to size

    Style Number/Barcode: 06001-5181

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Go With The Flow Frayed Denim Bucket Hat

    Top off your look in this denim bucket hat for any casual hangs! It features a classic bucket hat design with cool fraying and a short brim to help shade from the sun. Complete the look in platform sneakers.

    Fit & Features

    • Denim material
    • Frayed design
    • Short brim
    • Classic bucket hat design

    Style Number/Barcode: 07302-1613

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sun-Soaked Adventure Woven Metallic Flat Sandals

    Let these faux leather flat sandals lead you on a sun-soaked adventure! The square toe and studded trim add edgy detail while the woven strap brings a touch of boho-chic. Plus, the metallic adjustable ankle strap ensures a comfortable fit. Perfect for beach days, city strolls, and vacations! Complete the look with a trendy tote bag and sunnies.

    Fit & Features

    • Flat faux leather sole
    • Square toe
    • Woven pattern strap
    • Studded trim
    • Metallic adjustable ankle strap, buckle closure
    • Runs true to size

    Style Number/Barcode: 07404-1193

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Decadent Charm Rhinestone Twist Hoop Earrings

    Elevate your look and feel effortlessly glamorous in these rhinestone twist hoop earrings for a stunning look. The twisted hoop design and rhinestone embellishments add a touch of elegance and sparkle to any outfit. Made with a sleek metal hoop and secure omega closure, these earrings are stylishly chic! Pair with a flirty off-the-shoulder dress for a date night!

    Fit & Features

    • Twisted hoop design
    • Rhinestone embellished hoop
    • Sleek metal hoop
    • Omega closure


    Earrings are final sale and may not be returned or exchanged. 

    Style Number/Barcode: 07001-1963

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free