Vacation Looks

HomeVacation Looks
Loading...

Now Trending

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.

  • Botanical Beauty Off Shoulder Tunic

    Get into that out-of-office mood with this flowy tunic! It's never too early to start planning that getaway trip 

    Fits & Features

    • Off Shoulder Design 
    • Quarter Length Sleeves I Ruffle Cuffs 
    • Mini Length Silhouette I Ruffle Hem
    • Woven Fabric I Lined Skirt
    • Smocking At The Neckline, Cuffs & Midsection 
    • Form Hugging I Plenty Of Stretch

     

    Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06001-2472

    Category Name: Vacation Looks

    Price: $14.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Thing Ruffle Smocked Crop Top

    Compliment your sweet side when you style in a femme romantic smocked crop top!

    Fit & Features

    • Square neckline
    • Lace up center detail
    • Smocked bodice
    • Long chiffon sheer sleeves
    • Ruffled wrist | Ruffled hemline
    • Moderate stretch at smocked areas

    Style Number/Barcode: 06003-0767

    Category Name: Vacation Looks

    Price: $11.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Chiffon Tie Front Duster

    Chic and flowy, this tie front duster can easily be layered over your 'fits to make them all the more stylish.

    Fit & Features

    • Long loose sleeves | Elastic banded cuffs
    • Tie front belt
    • Flowy fit
    • Sheer chiffon fabric | No stretch

    Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 06204-0363

    Category Name: Vacation Looks

    Price: $16.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Met Your Match Smocked Mini Skirt

    Girl, we are SWOONIN' over your outfit! Charm them all in this look that's as sweet as you! 

    Shop Matching Top: Met Your Match Smocked Crop Top 

    Fits & Features

    • High Rise, Elastic Waistband
    • Smocking Throughout 
    • Ruffle Mini Length Hem 
    • Woven Fabric 
    • Curve Hugging Fit I Ample Stretch 
    • Matching Top Sold Separately 

    Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small. 

    Style Number/Barcode: 06401-0211

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Met Your Match Smocked Crop Top

    Girl, we are SWOONIN' over your outfit! Charm them all in this look that's as sweet as you! 

    Shop Matching Skirt: Met Your Match Smocked Mini Skirt

    Fits & Features

    • Smocked Bodice 
    • Lettuce Trim Square Neckline & Cropped Hem  
    • Adjustable Drawstring At Center Front 
    • Roomy Long Sleeves
    • Elastic, Ruffle Cuffs 
    • Matching Skirt Sold Separately 

     

    Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small. 

    Style Number/Barcode: 06003-0768

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fancy Fashionista Sunglasses

    You're a major fancy fashionista, and need some shades to match your style! These sunglasses will amp up any 'fit.

    • Cat eye shaped lenses
    • Plastic frame
    • Metal top rim
    • Dark tinted lenses
    • 100% UV Protection

    Style Number/Barcode: 07008-0700

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Money To Blow Rectangle Sunglasses

    Look expensive in a pair of shades, like u got money to blow, and places 2 be 

    • Wrap around lenses
    • Transparent frame
    • Rectangular design
    • Skinny 

    Style Number/Barcode: 07008-0702

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Live It Up Sunglasses

    Live it up and glam up your look with these flashy sunnies!

    • Large square shaped lenses
    • Metal open sides
    • Dark tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-0697

    Category Name: Vacation Looks

    Price: $5.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beach Bum Bikini Swim Top

    Lay out and indulge in the beach bum vibe this summer! What better way to soak up the sun than in a sexy bikini? Don't forget to pick up the matching bottoms to complete the look!

    Shop Matching Bottoms: Beach Bum Bikini Swim Bottoms

    Fit & Features

    • Triangle design
    • Tie-string closures
    • Fully lined
    • Removable padding
    • Moderate stretch | Sheen finish
    Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.    

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0319

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beach Bum Bikini Swim Bottoms

    Lay out and indulge in the beach bum vibe this summer! What better way to soak up the sun than in a sexy bikini? Don't forget to pick up the matching top to complete the look!

    Shop Matching Top: Beach Bum Bikini Swim Top

    Fit & Features

    • Mid-rise fit
    • Tie-string hip 
    • Fully lined
    • Moderate stretch | Sheen finish
    Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.    

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07105-0475

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Snake It Out Bikini Swim Top

    Get sassy in snake print this summer bae! The neutral tones compliment that tan, and give u a fierce finish! Don't forget to pick up the matching bottoms!

    Shop Matching Bottoms: Snake It Out Bikini Swim Bottoms

    Fit & Features

    • Triangle design
    • Halter tie closure + back tie closure
    • Removable padding
    • Fully lined
    • Snake print pattern
    • Moderate stretch
    Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.    

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0310

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Snake It Out Bikini Swim Bottoms

    Get sassy in snake print this summer bae! The neutral tones compliment that tan, and give u a fierce finish! Don't forget to pick up the matching bottoms!

    Shop Matching Top: Snake It Out Bikini Swim Top

    Fit & Features

    • Triangle design
    • String hips
    • Cheeky bottom
    • Fully lined
    • Snake print pattern
    • Moderate stretch
    Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.    
    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07105-0466

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Vibe Floral Print Strapless Bodycon Mini Dress

    Look gorgeous at your getaway and show off a bold vibe in this knit mini dress designed with a large floral print to turn heads. It features a strapless straight-across neckline and a short bodycon silhouette to hug your curves.

    Fit & Features

    • Smooth knit fabric with knit lining, plenty of stretch
    • Large floral print
    • Strapless straight neckline, no-slip strip
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6047

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • High Rise Distressed Cut Off Jean Shorts

    Everyone needs a classic pair of vintage looking cut offs in their closet! These shorts are perfect for spring break babe!

    Fit & Features

    • High rise waist
    • Traditional five pocket and belt loop design
    • Front button closure
    • Light distressed detailing
    • Cut off hem with slight fraying
    • Denim fabric

    Style Number/Barcode: 06603-0060

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Kailey High Rise Bermuda Denim Shorts

    Oasis by Eunina

    Summer can't come any sooner. Take a stylish cue and pair with your favorite bodysuit or a breezy blouse! 

    Fits & Features

    • High Rise Fit 
    • Traditional Five Pocket Styling 
    • Belt Loop Design  
    • Button Waist I Zip Fly 
    • Destructed Detailing 
    • Skinny Leg Fit I Hits Mid Thigh I Raw Edge Hem
    • Form Hugging Fit I Moderate Stretch 

    Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small. 

    Style Number/Barcode: 06603-0028

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Coastal Chic Linen Halter Maxi Dress

    Meet your vacay soulmate. This breezy maxi serves minimal effort with major impact thanks to its sleek halter neckline, open tie back, and flowy fit made for golden hour strolls or rooftop cocktails.

    Fit & Features

    • Linen-blend woven fabric
    • High halter neckline, spaghetti strap tie
    • Open back with spaghetti strap tie, lower zipper and hook-eye closure
    • High side slit
    • Flowy maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000026

    Category Name: Vacation Looks

    Price: $11.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bring On The Floral Mini Dress

    Bring on the bold floral with this absolutely adorable mini! The dress has a cute ruffle hem for major flirty vibes.

    Fit & Features

    • Tie shoulder straps
    • Slight sweetheart neckline
    • Parital stretchy smocked back
    • Hidden zipper | Hook and eye closure
    • High waist | Flowy short skirt | Ruffle hem
    • Woven fabric | Woven lining | No stretch
    • All over floral print

    Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0607

    Category Name: Vacation Looks

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Darling Floral Chiffon Top

    Keep it sweet in gorge florals! This charming top brings the romance with the lovely floral print! 

    Fit & Features 

    • Off The Shoulder Neckline | Built In No Slip Strip
    • Plunging V-Neck Bust | Single Button Closure
    • Built-In Flexible Boning | Long Sleeves
    • Floral Print
    • Sheer Lined Chiffon Fabric 
    • Relaxed Fit | Minimal Stretch 
    • Contrast Thong Bottom | Snap Button Closure 

    Style Number/Barcode: 06003-0333

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Got That Classic Vibe Jean Jacket

    Get that classic vibe by layering on this perf basic jean jacket. A closet essential for sure.

    Fit & Features

    • Long sleeves | Single buttons to cuff
    • Collared
    • Button down front
    • Two buttoned chest pockets
    • Two vertical pockets at the waist
    • Mid-length, form-fitting style
    • Denim fabric | Minimal stretch

    Style Number/Barcode: 06203-0055

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Jumping To Conclusions Denim Jumpsuit

    Were going to go ahead and jump to the conclusion that you absolutely need a denim jumpsuit in your life! Talk about an easy outift!

    Fit & Features

    • Square neckline
    • Spaghetti straps 
    • Criss cross back
    • Low back design | Lower back zipper closure
    • Straight leg
    • Medium wash denim | Moderate stretch
    • Slanted pockets

    Model is 5'7" with a 34" bust,  24" waist and 34" hips. She is wearing a size small.  

    Style Number/Barcode: 06602-0092

    Category Name: Vacation Looks

    Price: $21.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Always Be My Baby Shimmering Blouse

    Catch the moonlight on your date night in the most magical way! We are stunned over this beautiful blouse. Pair with high waist denim or a cute lil' mini skirt!

    Fit & Features

    • Sweetheart neckline
    • Long balloon sleeves
    • Cropped hemline
    • Vertical princess seams
    • Zipper closure center back + hook & eye closure
    • Elastic wrist + Shoulder sleeve
    • Woven knit with shimmering finish | Fully lined

    Style Number/Barcode: 06003-0455

    Category Name: Vacation Looks

    Price: $11.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • High Rise Button Up Cut Off Jean Shorts

    We all need that perfect pair of denim cut offs in our closet, and these high rise distressed shorts are a definite must have.

    Fit & Features

    • High rise waist
    • Five button down front
    • Five pocket and belt loop design
    • Destructed detailing
    • Frayed short hem
    • Denim fabric | Moderate stretch

    Style Number/Barcode: 06603-0031

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Smocked Over Florals Crop Top

    Get smocked over this floral trend this season with a cute crop top! 

    Fit & Features

    • Off The Shoulder Neckline
    • Smocked Bodice
    • Sheer Long Sleeves
    • Floral Print
    • Cropped Hem
    • Relaxed Fit 
    • Moderate Stretch 

    Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0387

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Eye Catcher Sparkling Denim Cropped Jacket

    Add a touch of sparkle to your casual look! This cropped denim jacket is perfectly paired with all of your go-to high waist bottoms, and can easily be dressed up or down!

    Fit & Features

    • Collared neckline
    • Long sleeves
    • Button down front
    • Double front pockets
    • Light wash denim | No stretch
    • Dusted in tiny rhinestone detailing
    • Cropped raw hemline

    Model is 5'9" with 32" bust, 23" waist and 36" hips. She is wearing a size small.    

    Style Number/Barcode: 06203-0049

    Category Name: Vacation Looks

    Price: $17.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance