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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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.

Flutter Sleeve Eyelet Tie Waist Romper
Step out in a trendy eyelet romper to make a chic statement. This must-have romper features a round neckline, short flutter sleeves, and a tie waist belt. The back features a lower back cut out to show off a hint of skin. The relaxed fit leads to a pair of wide-leg shorts. The romper is composed of woven eyelet fabric that offers a relaxed fit with minimal stretch. Complete look with wedges and fab earrings.

Fit & Features
- Round neckline
- Short flutter sleeves
- Tie-waist belt
- Eyelet
- Wide-leg shorts
- Relaxed fit with minimal stretch
Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06503-0090

Category Name: Vacation Looks

Price: $27.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Basic Sleeveless Strappy Back Ribbed Knit Bodysuit
Strap up in a ribbed knit bodysuit. This basic staple piece will take you from festival to dinner with the squad. It features a sleeveless bodice with a plunging scoop neckline, spaghetti straps, and a strappy back with tie back straps. The bodysuit is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete your minimal vibe with high waist shorts and dad sneakers.

Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Strappy open back
- Ribbed knit fabric
- Cheeky bottom
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small
Style Number/Barcode: 06001-2751

Category Name: Vacation Looks

Price: $6.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summertime Fine Crop Top
Show off that bod in this halter crop top! Rock it with denim shorts and booties and you’ll be looking hot for summer.

Fits & Features
- Halter Tie Neck
- Linen Fabric
- Drawstring Front
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-0680

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Miss Pretty Ruffle Crop Top
Your wardrobe is missing some ruffles! Style this pretty top with denim, heels and a trendy mini bag.

Fit & Features
- Ruffle off the Shoulder Trim
- Cropped Hem
Model is 5'9" with a 32" bust, 24" waist and 36" hips.
Style Number/Barcode: 06005-0646

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Boho Honey Tie Front Gauze Top
This paisley print crop top is giving us major boho vibes. Style it with high waist denim shorts and heels for the perf summer look!

Fits & Features
- Plunging V Neckline
- Adjustable Wrap Tie Detail
- Batwing Sleeves
- All Over Paisley Print
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-0917

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Endless Vacation Tie Front Swim Top
That's the dream, an endless vacation! The good news is that you have a swimsuit in your collection that lives through the season! Don't forget to pick up ur matching bottoms!

Shop Matching Bottoms: Endless Vacation High Waist Swim Bottoms

Fit & Features
- Triangle design
- Tank straps
- Tie front closure
- Removable padding
- Pull over design
- Moderate stretch
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0403

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Charmed In Ruffles Peplum Top
Charm them all in pretty ruffles! This frilly top perfectly pairs with your fav denim and statement earrings!

Fit & Features
- Off The Shoulder Neckline | Ruffled Trim
- Smocked Bodice
- Peplum Hem
- Lined Smocked Knit 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: 06003-0579

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Major Babe One Shoulder Crop Top
Hey major babe! Get a stunning, sexy look in this one shoulder crop top! Pair it with some light wash high rise distressed jeans or a sleek satin midi skirt to dress it up!

Fit & Features
- One shoulder neckline
- Tank-like shoulder strap
- Sweetheart twist front
- Exposed back zipper
- Cropped | Drop detail
- Ribbed knit fabric
Style Number/Barcode: 06003-0799

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Cork Slide On Wedges
Simply slide into style with these classic wedges. Composed of a cork designed wedge, and a clear PVC upper. Pair with all your summer faves for an effortless look!

Style Number/Barcode: 07406-0045

Category Name: Vacation Looks

Price: $12.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bloom With Beauty Maxi Dress
Be a stunning blooming beauty in this floral printed maxi dress!

Fits & Features
- V Neckline
- Spaghetti Straps
- Sheer Lace Back With Zipper I Elastic Back Cut-Out
- High Waist Seam
- Flowy, Maxi Length
- Sheer Chiffon Fabric I Knit Lining
- Relaxed Fit I Minimal Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
*Also available in Plus.
Style Number/Barcode: 05102-3887

Category Name: Vacation Looks

Price: $24.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Keep It Breezy Square Toe Jelly Rhinestone Sandals
Are you ready for this jelly? You will be when you are sitting pool side with this cute pair!
- Open square toe
- Rhinestone embellished strap
- Ankle strap closure
- Composed of jelly material
- Flat sole
Style Number/Barcode: 07404-0105

Category Name: Vacation Looks

Price: $14.90

Availability: Out of Stock
Product Badge:
- Ships Free
Getaway Girl Floral Smocked Tube Maxi Dress
Girl, you'll look stunning on your weekend getaway in this floral tube maxi dress! It features a strapless square neckline, a smocked bodice, and a flowy maxi-length silhouette with a ruffle bottom hem. Don't forget to add a pair of wedges and a wide brim hat to your cart as well!

Fit & Features
- Strapless square neckline
- Stretchy smocked bodice
- Maxi-length silhouette, mini-length lining
- Ruffle bottom hem
- Floral printed woven fabric
- No stretch
- Runs true to size
Style Number/Barcode: 05101-0033

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chill Out High Waist Shorts
Chill out girl and leave the drama behind with this must have high waist shorts! Pair these cuties with a daring crop for an effortlessly put together look!

Fit & Features
- High Rise Waist
- Single Button and Zipper Closure
- Traditional Five Pocket and Belt Loop Design
- Cut Off Raw Edge Hem
- Light-Medium Wash Denim Fabric
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06603-0120

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Off To Paradise Wide-Leg Abstract Pants
A trending abstract pants designed with a flattering high-rise waist and a wide-leg design that flaunts your figure on vacay! Pair with the matching top to complete the look.

Fit & Features
- Abstract print, stretchy knit fabric
- High-rise waist
- Wide-leg silhouette
- Runs true to size
Shop The Matching Top: Off To Paradise Tie-Front Crop Top
Style Number/Barcode: 06502-000010

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Oh So Dreamy Tie Dye Mini Skirt
Get an oh so dreamy look in this trendy tie dye mini skirt! Pair with a pastel hued simple tank and some strappy mules for the perf spring time vibe!

Fit & Features
- High rise elastic banded waist
- Ruched side detailing | Ties at hem
- Short, curve hugging fit
- All over tie dye print
- Soft knit fabric | Plenty of stretch
Style Number/Barcode: 06501-0215

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Keep The Confidence Criss-Cross Platform Heels
Stand tall and confident when you pair your summer dress with the perfect platform heels!
- Open pointed toe
- Criss cross over the toe straps
- Ankle strap + closed heel
- Adjustable o-ring pin buckle closure
- Faux suede
- Cork style platform heel
Style Number/Barcode: 07401-2260

Category Name: Vacation Looks

Price: $23.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
A Little Daytime Fun Platform Cork Heels
Have your self a little day time fun when you step out in these summer ready platform heels! These would look so cute with your straw hat and summer dress!
- Open almond toe
- Faux leather
- Single band over the toe
- Ankle strap
- Adjustable pin buckle closure
- Platform heel
- Cork sole
Style Number/Barcode: 07401-2259

Category Name: Vacation Looks

Price: $23.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Slide Into Basics Faux Leather Sandals
Slide into a closet staple when you style these simple faux leather slides with all of your summer looks!
- Open almond toe
- Single band over the toe
- Faux leather
- Slide on fit
Style Number/Barcode: 07404-0588

Category Name: Vacation Looks

Price: $9.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Basic Straw Wide Brim Floppy Hat
Head outdoors with a chic floppy hat. Keep your tresses on point with a dramatic floppy hat that features an all-over straw-like material and a traditional wide brim to shield eyes. Add a floppy hat to complete a vacay outfit or give your maxi dresses a diva-approved touch.

Fit & Features
- Traditional floppy structure
- Wide brim
- Straw-like material
Style Number/Barcode: 07302-0208

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Faux Leather Wide Strap Slide Sandal
Minimal slide sandals are a must. These versatile slides feature a comfortable single wide strap to easily slip on, an open toe and a flat sole. Sandals are composed of faux leather material. Easily pair these sandals with floral sundresses or monotone basics to create a minimal look from head to toe.

Fit & Features
- Open toe
- Wide single strap
- Flat sole
- Faux leather material
Style Number/Barcode: 07404-0589

Category Name: Vacation Looks

Price: $9.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Standing Tall Flat Platform Sandals
Stand a lil taller when these 90z inspired platform sandals! Style with a sweet summer dress, or some cut off denim!
- Open round toe
- Single band over the toe
- Sling back ankle strap
- Adjustable pin buckle closure
- Faux leather
- Faux nubuck straps
- Platform sole
Style Number/Barcode: 07404-0189

Category Name: Vacation Looks

Price: $7.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cloud Dye Tulip Pajama Shorts
A pair of cloud dye shorts is a must-have. The dreamy pair feature a high elastic waist, a pastel-hued cloud dye print, a tulip hem opening, and a cheeky fit. Pair the shorts with the matching bralette and complete your look with a cozy set of slides.

Shop Matching Bralette: Cloud Dye Triangle Bralette

Fit & Features
- High-rise elastic waist
- Cloud dye pattern
- Tulip hem opening
- Cheeky fit
- Runs true to size
Style Number/Barcode: 07103-0322

Category Name: Vacation Looks

Price: $9.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cloud Dye Triangle Bralette
A cloud dye bralette is a must-have. The dreamy bralette features adjustable spaghetti straps for a customized fit, flattering triangle cups, and an elastic band for a secure comfortable fit. Pair the bralette with the matching shorts and a pair of slides for a completely cozy vibe.

Shop Matching Shorts: Cloud Dye Tulip PJ Shorts

Fit & Features
- Cloud dye pattern
- Triangle cups
- Adjustable spaghetti straps
- Elastic hem with matching elastic band
- Runs true to size
Style Number/Barcode: 07107-0430

Category Name: Vacation Looks

Price: $2.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summer Starts Now Rhinestone Jelly Slides
Summer starts now, and its already a sparkling one! Slide into these babies and hit the pool babe!
- Open square toe
- Slide on design
- Rhinestone trim
- Rhinestone embellished band over the toe
- Composed of jelly like material
Style Number/Barcode: 07404-0641

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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Vacation Looks

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STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials