Vacation Looks
Vacation dressing should be easy, stylish, and ready for wherever the day takes you. Start with mini sundresses and flirty rompers that work for both sightseeing and rooftop drinks at sunset. Add in flowy maxis, crochet cover-ups for poolside sunbathing, and sleek sunnies that instantly pull a look together. From cutoff denim shorts to swimwear with eye-catching details, these outfits keep your suitcase light and your style on point for every getaway moment.
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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.
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Boho Feels Tie Front Top
Get all those boho feels in this flowy tie front top! Wear as a cute top or over your fave swimsuit poolside!
Fit & Features
- Flowy three quarter length sleeves
- V neckline
- Tie front
- Cropped
- Striped
- Lighweight, textured crepe fabric
- No stretch
Style Number/Barcode: 06204-0482
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Color Splash Tie Dye Tie Front Kimono
Make a splash in your outfit with this gorge kimono! Layer it on for a trendy lewk on the beach

Fits & Features
- Drape Open Front
- Kimono Sleeves
- Slits At The Sides
- Woven Gauze Fabric I Tie Dye Print I Fringe Trim
- Relaxed Fit
- Minimal Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06204-0433
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Basic Vibes Denim Jacket
Fall back on basics to complete your look! A denim jacket is a must-have for this season! Pair with your favorite pastel pieces for a Spring ready look!
Fit & Features
- Collard Neckline
- Button-Down Front
- Long Sleeves | Single Button Cuff
- Side Pockets
- Light Medium Wash Denim Fabric
- Relaxed Fit
- Minimal Stretch
Model is 5'4" with a 32" bust, 23" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06203-0042
Category Name: Vacation Looks
Price: $11.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Basic Cropped Tube Top
Stick to the basics with this classic crop top!
Fit & Features
- Straight, strapless neckline
- Flattering slim fit
- Heathered knit
- Plenty of stretch for comfort
Style Number/Barcode: 06002-5398
Category Name: Vacation Looks
Price: $6.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spring Fling Tie Front Top
We love a good spring time lewk! Pair this adorable tie front crop top with your fave satin midi skirt and some chic heels.
Fit & Features
- Long puff sleeves | Smocked arms
- Tie front detail
- Cropped
- Lightweight, cotton blend fabric
- No stretch
Style Number/Barcode: 06204-0591
Category Name: Vacation Looks
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Denim Sweetheart Lace Up Crop Top
Hey babe! You'll look like a total sweetheart in this adorable denim lace up crop top, perf paired with some white shorts and matching white booties!
Fit & Features
- Adjustable spaghetti straps
- Sweetheart neckline
- Lace up front
- Exposed back zipper closure
- Cropped
- Denim fabric
- Relaxed Fit | Moderate Stretch
Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06003-0520
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer-Coded Crochet Halter Mini Dress
Serve all the summer vibes in this crochet knit mini dress designed with a halter V-neck with a beaded trim on the straps. Style with espadrille wedges for sunset happy hour.
Fit & Features
- Sheer crochet knit fabric with knit lining, moderate stretch
- Sleeveless V-neckline
- Tie-back halter straps, beaded trim
- Partially open back
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-6114
Category Name: Vacation Looks
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Dream Kimono Sleeve Top
Look like a total dream in this gorgeous floral kimono sleeve top! Pair with some high rise denim cutoffs for the perf spring vibe.
Fit & Features
- Three quarter length flowy kimono sleeves
- V neckline
- Tie front detail
- Cropped
- All over floral print
- Polyester woven fabric
Style Number/Barcode: 06204-0558
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Why Knot Flutter Sleeve Chambray Tie Front Top
Perfect for sunny days and adding a sultry touch to your look. Tie up your look with this adorbs flutter sleeve top!
Fits & Features
- Adjustable Center Front Tie
- Plunging V Neckline
- Short, Flutter Sleeves
- Crop Hemline
- Chambray Fabric
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06204-0462
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic Vibes Tie Front Top
Give off some seriously chic vibes in this fab tie front top that will keep you on trend babe! Pair this tie front top with your fav high waist denim and strappy sandal or fun wedge heel!
Fit & Features
- Tie Front Bodice
- Quarter Length Sleeves
- Puff Sleeves
- Cropped Hem
- Floral Print
- Lightweight Woven Fabric
Style Number/Barcode: 06204-0549
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tied Down Flutter Sleeve Tie Front Top
Get tied down to this cute top! Perfectly paired with denim skinnies or cut-offs, feel chic and fresh with this outfit topper!
Fits & Features
- Plunging V Neckline
- Center Tie Front
- Double Layer, Short Flutter Sleeves
- Woven Lightweight Gauze Fabric
- Cropped Hem
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06204-0499
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dream State Chiffon Floral High Low Duster
"I must be dreaming". Hit 'em with an entrance in this dreamy and romantic duster! A perfect layering piece over your bikini set, you can also work your charm by pairing it over a tube top and some denim cut-offs!
Fits & Features
- Short Flutter Sleeves
- Plunging V Neckline I Empire Waist With Triple Button Closure
- High-Low Hem
- Sheer Chiffon Fabric
- Floral Prints Throughout
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06204-0387
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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In My Feels Scoop Neck Bra Top
Whether you're on vacay or sitting poolside, this scoop neck bra top will have you feeling yourself! Pair with the matching skirt.
Fit & Features
- Stretchy knit fabric
- Spaghetti straps
- Scoop neckline
- Ultra-cropped hem
- Runs true to size
Shop The Matching Skirt: In My Feels High-Rise Midi Skirt
Style Number/Barcode: 06005-2257
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Flirt Ruffle Detail Romper
Give off major flirty vibes in this adorable ruffle detail romper! With a tie front accent and on trend mint hue, this romper will have you totally spring ready.
Fit & Features
- Off the shoulder sweetheart neckline | Spaghetti straps
- Sheer flowy short sleeves
- Ruffle overlay
- High waist | Side tie detail
- Flowy shorts
- Dainty trim detail
Style Number/Barcode: 06403-0096
Category Name: Vacation Looks
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sassy Smocked Ruffle Detail Crop Top
Sassy and smocked, this ruffle detail crop top is a must-have for this spring season! Pair it with some trendy light wash denim shorts for the perf warm weather look.
Fit & Features
- Strapless square neckline
- Smocked knit fabric
- Ruffle detail trim
- Cropped
Style Number/Barcode: 06001-2735
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Living Fine in Rhinestones Sandals
Show off your affinity for that luxe life in these dazzling rhinestone sandals that easily dress up your most casual lewks!
- Mid-Calf Length Wrap Around Strap
- Rhinestone Embellished and Beaded Strap
- Flat Sole
- Faux Leather Material
Style Number/Barcode: 07404-0638
Category Name: Vacation Looks
Price: $12.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Carry On Vibrant Snake Mini Purse
Keep doin' you boo-boo! Add a pop of color and hold all your essentials in this trendy mini purse. Make room for your newest addition bb!- Rectangular Design
- Top Handle
- Snap Button Closure
- Detachable And Adjustable Nylon Shoulder Strap
- Multi Vibrant Textured Snake Print
Style Number/Barcode: 07203-0334
Category Name: Vacation Looks
Price: $11.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Hips Don't Lie Cubic Zirconia Dainty Chain Belt
Accentuate those hips a little when you add a little body jewelry in the mix! This stunning hip chain is the perfect way to level up that swim look!
- Cubic zirconia rhinestones
- Adjustable lobster clasp closure
- Chain link design
- Dainty
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 07002-0446
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On The Move Double Band Platform Sandals
Babe you are about to be on the move real soon and why not make sure you have the cutest sandals on hand! Pair with high waist shorts, or even a linen midi skirt!
- Open round toe
- Double band design
- Cork detailing
- Sport platform sole
Style Number/Barcode: 07404-0657
Category Name: Vacation Looks
Price: $14.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spring Affair Puff Sleeve Crop Top
Style yourself with spring in mind! This ever so floral cropped top is a sunny day essential. Pair with white high waist denim, or even a mini skirt!
Fit & Features
- Sweetheart neckline
- Quarter puff sleeves
- Form fitting
- Tie front detail
- Smocked back
- Smooth knit
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-0576
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Set The Tone Halter A-Line Floral Midi Dress
Set the tone for spring dressing in this halter floral midi dress designed in a statement A-line silhouette perfect for brunch, garden parties, and day dates!
Fit & Features
- Floral print, woven fabric, woven lining
- Sweetheart halter neckline, tie-back design
- Back zipper and hook-eye closure
- A-line silhouette
- Flowy midi-length hem
- Runs true to size
Style Number/Barcode: 05101-3969
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Such A Gem Vintage Bohemian Ring 5 Pack
Add a vintage touch to your look when you style in some stunning boho rings! It's the little things that make your look come to life!
- Set of five rings
- Vintage boho design
- Gemstone detailing
- Gold rustic finish
Style Number/Barcode: 07004-0074
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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The Perfect Touch Gold Cuff Bracelet
We have the perfect touch for your look! Adding in an arm cuff to your sleeveless dress gives it a fun twist!
- Four rows
- Open ended
- Simple rhinestone detailing
- Available in silver
Style Number/Barcode: 07003-0102
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Island Time Straw Fringe Clutch
Girl, we know you're on that out-of-office, do not disturb, runnin' on island time mood when you bust out this clutch! Pairs perfectly with a marg and that vacay set you got packed!
- Long Rectangular Structure
- Snap Button Closure
- Main Compartment With Interior Pocket Sleeve
- Straw Composition I Fringe Detail
Style Number/Barcode: 07203-0324
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free