Vacation Looks

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STYLE SPOTLIGHT

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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.

  • Chic Addition Dainty Stone Threader Earrings

    These dainty stone threader earrings will be a chic addition to your jewelry lineup! They feature a long delicate chain threader design accented with small teardrop clear stones at the front and sleek bar detailing at the back. Style with a layered necklace for a trendy luxe vibe.

    Fit & Features

    • Long dainty chain threader design
    • Front teardrop clear stone accents
    • Back bar accents
    • Rubber stopper

     

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

    Style Number/Barcode: 07001-2039

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Statement Gleam Buckle Thong Sandals

    Make a statement in these buckle thong sandals perfect for elevating your spring to summer style!

    Fit & Features

    • Square toe
    • Buckle accent thong strap
    • Flat sole
    • Style Options: solid black, zebra print, ivory
    • Runs true to size

    Style Number/Barcode: 07404-1247

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: In Stock

    Available Color: ZEBRA

    Available Size: 5.5, 6, 6.5, 7, 7.5

    Product Badge:
    • Sale
  • Dreamy Sparkle Celestial Charm Lariat Necklace

    This celestial charm lariat necklace will showcase the dreamiest sparkle! It features a dainty chain, an O-ring and toggle closure, a long cascading lariat design, shimmering rhinestones, and sleek moon and star charms for a trendy pop. Pair with stud earrings.

    Fit & Features

    • Dainty chain
    • O-ring and toggle closure
    • Rhinestones
    • Moon and star charms
    • Long lariat design

    Style Number/Barcode: 07002-1846

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Poolside Paradise Floral Scrunch Bikini Bottoms

    So pretty and made for tanning, these floral bikini bottoms offer a flattering V-shaped low-rise waist and a scrunched thong back that flaunts your curves! Pair with the matching bikini top.

    Shop Matching Top: Poolside Paradise Floral Triangle Bikini Top

    Fit & Features

    • Floral print, stretchy knit fabric
    • V-shaped low-rise waist
    • Scrunched thong back coverage
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000010

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stand Out Texture Oval Hoop Earrings

    Stand out in these hoop earrings featuring a textured oval design and post-back closures. Perfect for styling your everyday outfits.

    Fit & Features

    • Textured oval design
    • Post-back closure

     

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

    Style Number/Barcode: 07001-2063

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Babe Gingham Print Bandeau Bikini Top

    Channel that flirty babe style in this adorable gingham printed bandeau bikini top with a ruffled trim. Pair with the matching bikini bottoms for a sweet and sassy look.

    Shop Matching Bottoms: Flirty Babe Gingham Print Side Tie Bikini Bottoms

    Fit & Features

    • Nylon-blend fabric, high stretch
    • Gingham print
    • Strapless neckline
    • Center bust cutout, tie-front detail
    • Ruffled trim
    • Thin strappy back design, hook and bar closure
    • Runs true to size

    Style Number/Barcode: 07104-0718

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Head Turner Floral Bodycon Mini Dress

    With a sultry strut and this floral mini dress, you'll be a major head turner on vacation or at parties! 

    Fit & Features

    • Floral print, knit-lined stretchy fabric
    • Strapless neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000103

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty Chic Floral Chain Necklace

    This cute necklace features a dainty flat floral chain design perfect for adding to your layered necklace stack. Complete your pretty chic look with hoop earrings.

    Fit & Features

    • Dainty flat floral chain
    • Back adjustable chain with lobster clasp closure

    Style Number/Barcode: 07002-1862

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Romantic Allure Flutter Sleeve A-Line Lace Mini Dress

    Indulge in the romantic allure of this lace mini dress with pretty flutter short sleeves and a flattering A-line silhouette. Perfect for shower celebrations, graduations, or brunch!

    Fit & Feature

    • Lace lined fabric
    • Flutter short sleeves
    • V-neckline
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4015

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charmed Sweetness Lace-Up Floral Skater Dress

    Charm everyone with your sweetness in this floral skater dress with a flirty lace-up back and a ruffled short hem perfect for any weekend plans.

    Fit & Features

    • Floral print, woven fabric, bust lining
    • V-neckline, wide shoulder straps, padded bra cups
    • Lace-up back
    • Ruffled skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5622

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • New Moon Star Charm Layered Necklace

    Get in touch with your celestial style in this layered necklace featuring a moon and star charm and mini clear stones that put your outfit out of this universe! Complete the look in heels.

    Fit & Features

    • Two-row layered design
    • Moon and star charm
    • Mini clear stones
    • Lobster clasp closure

    Style Number/Barcode: 07002-1870

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Paradise Babe Lace Up Tropical Floral Maxi Dress

    Look like a babe in paradise in this tropical floral maxi dress perfect for your next getaway or beach day! Embrace the warm, tropical vibes in this maxi-length hem dress on an airy mesh fabric bursting with a tropical floral print.  With its flowy silhouette and high slit, you'll feel like you're walking on clouds. The V-neckline and spaghetti straps add a trendy vibe while the lace-up detail adds a touch of playfulness. Complete the look in sandals and sunnies!

    Fit & Features

    • Tropical floral print
    • Mesh fabric lined with knit, moderate stretch
    • Lace-up
    • Spaghetti straps
    • High slit
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3241

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Grandeur Blooms Strapless Slit Floral Maxi Dress

    Gorgeous blooms dance across this floral maxi dress making every entrance statement worthy! Perfect for cocktail parties or dressy dinners, this strapless dress boasts a form-hugging fit, a high side slit allowing for movement, and a maxi-length hem. Complete the look with a clutch purse and heels.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • Strapless neckline
    • High side slit
    • Form-hugging fit
    • Runs true to size
    • Please note flower placement may vary

    Style Number/Barcode: 05101-3386

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Delicate Charm Layered Necklace

    Delicate and divine, this charm-layered necklace will complete your look beautifully! Style with a dressy jumpsuit for date night.

    Fit & Features

    • Delicate layered design
    • Two charms
    • Lobster clasp closure

    Style Number/Barcode: 07002-1874

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stay Sweet Short Sleeve Button Romper

    Stay sweet for everything on your social calendar in this short sleeve button romper designed with a layered ruffled hem that gives a flirty allure!

    Fit & Features

    • Woven fabric, knit lining, shorts underneath
    • Short sleeves
    • V-neckline, faux button details
    • Back zipper and hook-eye closure
    • Layered ruffled short hem
    • Runs true to size

    Style Number/Barcode: 06403-1102

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beachy Bombshell Bikini Top

    Beachy bombshell will be your vibe in this sweetheart bikini top designed with lurex knit fabric for a trendy metallic sheen. Pair with the matching bikini bottoms and sarong for a sun-kissed look!

    Shop Matching Set: Beachy Bombshell One-Shoulder Bikini Top, Beachy Bombshell V-Cut Bikini Bottoms, Beachy Bombshell Short Sarong

    Fit & Features

    • Lurex knit fabric, metallic sheen
    • Structured sweetheart bust with underwire, padded bra cups
    • Adjustable spaghetti straps
    • Back hook and bar closure
    • Runs true to size

    Style Number/Barcode: 07104-0724

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Choice Sleeveless Lace-Up Floral Romper

    A flirty floral romper like this is perfect for upcoming summer parties! Designed with a lightweight floral-printed woven fabric, it features a square neckline, a small keyhole cutout with a bust tie, thin shoulder straps, a lace-up back that adds a touch of flair, and a flowy short-length hem that keeps you trendy. Complete the look with hoop earrings.

    Fit & Features

    • Floral print
    • Woven fabric with smooth woven lining, no stretch
    • Square neckline with keyhole cutout and bust tie
    • Thin shoulder straps
    • Lace-up back, lower back zipper
    • Flowy short-length hem
    • Runs true to size

    Style Number/Barcode: 06303-0256

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Burst With Beauty Rhinestone Star Necklace

    Burst with dainty beauty with this rhinestone star charm necklace! Complete the look with a stackable ring set for extra glam. 

    Fit & Features

    • Rhinestone star charm 
    • Lobster clasp closure
    • Chain

    Style Number/Barcode: 07002-1866

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Thriving Allure Sweetheart Floral Romper

    Cue the weekend trip or brunch! This sweetheart floral romper will sweeten up all of your social plans.

    Fit & Features

    • Floral print, woven fabric, stretchy knit shorts lining
    • Lace trim sweetheart neckline, underwire bust
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Flowy short-length hem
    • Runs true to size

    Style Number/Barcode: 06503-1255

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Captivating Cutie Eyelet Floral Babydoll Dress

    Captivate everyone with your cuteness in this eyelet floral babydoll dress at parties or brunch! Made with delicate eyelet floral chiffon fabric, this dress is perfect for any occasion.  The puff short sleeves and V-neckline add a touch of playfulness, while the babydoll silhouette and tiered ruffled hem offer a flattering fit. Complete the look in edgy booties.

    Fit & Features

    • Eyelet floral print chiffon fabric lined with stretchy knit
    • Back zipper and hook-eye closure
    • Babydoll silhouette
    • Tiered ruffle short length hem
    • Runs true to size

    Style Number/Barcode: 05101-3144

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glittery Goals Triangle Rhinestone Threader Earrings

    Enchant everyone in these unique threader earrings featuring a dainty chain adorned with a triangle charm with mini rhinestone trim for a glittery effect. Complete the look with a ring set.

    Fit & Features

    • Dainty chain
    • Triangle charm with mini rhinestone trim
    • Threader-style silhouette
    • Rubber back stopper

     

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

    Style Number/Barcode: 07001-2060

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cool Girl Studded Western Buckle Sandals

    Slide into these studded western buckle sandals for a cool-girl vibe all spring to summer!

    Fit & Features

    • Round toe
    • Studded buckle dual straps
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1256

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beachy Bombshell Short Sarong

    Beachy bombshell will be your vibe in this short sarong designed with lurex knit fabric for a trendy metallic sheen. Layer over the matching bikini top and bottoms for a sun-kissed look!

    Shop Matching Set: Beachy Bombshell Bikini Top, Beachy Bombshell One-Shoulder Bikini Top, Beachy Bombshell V-Cut Bikini Bottoms

    Fit & Features

    • Lurex knit fabric, metallic sheen
    • Mini-length hem
    • Tie closure

    Style Number/Barcode: 07105-000003

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Honky Tonk Honey Two-Tone Baseball Cap

    This baseball cap features a trendy two-tone design embroidered with a script reading, "Honky Tonk Honey," and includes a back adjustable strap for a customized fit. Pair with a basic tee and jean shorts!

    Fit & Features

    • Cotton material
    • Curved brim
    • Two-tone design
    • Embroidered script reads, "Honky Tonk Honey"
    • Back adjustable strap

    Style Number/Barcode: 07302-1685

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale