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.

Bronzed And Boujee Side Hook Swimsuit
Girl you are bronzed and boujee this summer in your sexy one piece swimsuit!

Fit & Features
- Two piece bathing suit
- Hook clips at the hips + hook clips at sides of top
- Tank top with scoop neckline
- High rise bikini bottoms
- Lined
- Moderate stretch
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0174

Category Name: Vacation Looks

Price: $18.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Deep Reflections Ombre Aviators
Get lost in thought with Our Deep Reflections Aviators! Easily paired with all outfits, especially if you are feelin' a grungy look!
- Ombre lenses
- Aviator design
- Dainty arms
- Skinny frame
Style Number/Barcode: 07008-0751

Category Name: Vacation Looks

Price: $5.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chic Cat Eye Flat Top Sunglasses
Give your look a chic edge with these trendy cat eye sunnies!
- Flat top design
- Plastic frame
- Dark tinted lenses
- 100% UV Protection
Style Number/Barcode: 07008-0681

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Belted Button Detail Paper Bag Shorts
So chic, these belted button detail paper bag shorts will instantly elevate your look! Pair with some oversize sunnies for that it girl vibe.

Fit & Features
- High rise elastic banded paper bag waist
- Belt with tortoise shell O-ring buckle
- Parital button down front
- Slanted front pockets
- Woven fabric | Minimal stretch
Style Number/Barcode: 06303-0059

Category Name: Vacation Looks

Price: $13.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sweet Surprise Wide Leg Jumpsuit
Create a sweet charming look in this super gorge jumpsuit! It features a sleeveless bodice, a plunging sweetheart neckline, a tie front accent with keyhole, narrow adjustable straps and a smocked back. The bodice leads to a pair of wide leg pants with high center slit for a dramatic flare! Jumpsuit is composed of a lightweight woven fabric that offers a form hugging fit with minimal stretch.

Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 06302-0144

Category Name: Vacation Looks

Price: $17.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Vacay Mode Smocked Mini Skirt
A suitcase staple! The Vacay Mode skirt is perf for wearing with matching skirt for a cute, laid back look. All you need is that refreshing marg

Shop Matching Top: Vacay Mode Tie Front Blouse

Fits & Features
- Smocked
- High waist fit
- Mini hemline
- Woven Fabric
- Tropical Palm Print
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 06301-0044

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Easygoing Elegance Ruffle Detail Jumpsuit
Give your separates a break and slip into this beautiful jumpsuit! Girl, you'll look gorge from top to bottom!

Fits & Features
- Crew Neckline
- Ruffle-Trim Short Sleeves & Overlay At Front Bodice
- Button Down Front
- Belt Loop I Tie Waist
- Slip Hand Pockets
- Tapered Pant Leg
- Cotton Blend Lined Fabric I Moderate Stretch I Eyelet Design All Over
Style Number/Barcode: 06302-0135

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sunz Out Frayed Denim Mini Skirt
Sunny days are ahead, and we can't wait to live in denim mini skirts and cute crop tops!

Fit & Features
- High waist fit
- Button + Zipper closure
- Traditional pockets + belt loops
- Frayed mini hemline
- Light wash denim fabric | Moderate stretch
Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06601-0010

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Romantic Ruched Rose Print Mini Skirt
Bring on the romantic vibes in this ruched rose print mini skirt! Pair with a flowy chic cropped blouse and some heels for a beyond gorg look.

Fit & Features
- High rise elastic banded waist
- Hidden side zipper closure
- Side ruched detailing | Faux drawstrings at hem
- Short form hugging fit
- Rose printed woven fabric | No stretch
- Knit lining | Moderate stretch
Style Number/Barcode: 06401-0223

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Cute Direction Pointelle Skater Mini Dress
With a cute pair of sandals and this pointelle skater mini dress, everyone will be talking about what a cutie you are!

Fit & Features
- Pointelle knit fabric
- Scoop neckline, wide shoulder straps
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-2260

Category Name: Vacation Looks

Price: $44.90

Availability: Out of Stock
Product Badge:
- Ships Free
High Rise Cropped Jeans
Elevate your style with these must-have crop jeans! Pair these high-waist beauties with a cute crop or a fringe top!

Fit & Features
- High Rise Waist
- Single Button and Zipper Closure
- Traditional Five Pocket and Belt Loop Design
- Straight Leg Fit
- Heavy Distressed Detailing | Cropped Hem
- Light Wash Denim Fabric
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 06602-0149

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Babe Alert Button Front Jean Mini Skirt
Watch out, a total babe is coming through. Psst! It's you! In this adorable jean mini skirt.

Fit & Features
- High rise waist
- Complete button down front
- Two slanted front pockets | Two back pockets
- A-line fit
- Washed denim fabric | No stretch
Denim: Model is 5'9" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06601-0019

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Trendy Twist-Front Skater Romper
Bring the cute and trendy vibes with this adorable twist-front skater romper! It features a sleeveless bodice, spaghetti straps, a V-neckline with a twist-front detail, a small keyhole cutout below, a high waistband, and shorts with a flowy skater skirt overlay. The romper is composed of a crepe fabric that offers a moderate stretch. Style this romper with neutral heels.

Fit & Features
- Sleeveless V-neckline
- Twist-front design, front keyhole cutout
- Spaghetti straps
- High waistband
- Fitted shorts, skater skirt overlay
- Crepe knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-1006

Category Name: Vacation Looks

Price: $16.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Mesh Moment Cover Up
Relax poolside with this essential cover-up to pair with your fav swimsuits! It features trendy short kimono sleeves, a drawstring tie waist for a custom fit, and a flowy, longline hem. Complete the look in a sultry bikini.

Fit & Features
- Kimono short sleeves
- Drawstring tie waist
- Duster Length
- Relaxed silhouette
- Sheer unlined mesh fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06202-0153

Category Name: Vacation Looks

Price: $10.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Vacay Mood Tropical Print Halter Cutout Jumpsuit
This sultry tropical print jumpsuit will put you in the vacay mood! Designed with sleek knit fabric, it features an alluring cutout below the bust, a high-rise waist with a hip-hugging fit, and a trendy wide-leg silhouette.

Fit & Features
- Smooth knit fabric with knit bust lining, high stretch
- Tropical print
- Sleeveless scoop neckline, cutout below the bust
- Tie-back halter spaghetti straps, partially open back
- High-rise waist, hip-hugging fit
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-000011

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flutter Baby Tie Front Crop Top
Show off that flutter in this floral crop top! Style this with some high waisted jeans and cute clear strap heels for a cute af outfit!

Fits & Features
- Plunging V Neckline
- Tie Front Design
- Short Flutter Sleeves
- Smooth Woven Fabric I Floral Print
- Moderate Stretch
Style Number/Barcode: 06204-0501

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Viper Vibe Chiffon Kimono
Feminine, flowy, with a little bit of edge! Spice up your outfit with a touch of snake print!

Fits & Features
- Open Front
- Quarter Length Sleeves
- Sheer Chiffon Fabric I Snake Print Trim Along The Edge
- Relax Fit
Style Number/Barcode: 06204-0418

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
So Fab In Fringe Crop Top
You'll look so fab in fringe in this mesh tie front crop top bb! Perfect for festival season, your 'fit will be one to remember.

Fit & Features
- Long fitted sleeves | Cascading fringe
- Tie front
- Cropped
- Sheer mesh fabric | Unlined
- Plenty of stretch
Model is 5'9" with 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06202-0067

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Make My Heart Flutter Lace Tie Front Cropped Blouse
Keep things fresh and flirty for spring and summer when you style a lace cropped blouse with all of your high waist denim! Dress down with cute espadrille sandals or dress it up with heeled mules!

Fit & Features
- Tie front bodice
- Fluttering short ruffled sleeves
- Cropped hemline
- Sheer lace design
- Form fitting
- Minimal stretch
Style Number/Barcode: 06204-0515

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Don't Mesh With Me Kimono
No one will stand in your way in this trendy sheer mesh kimono! Layer it over all your best 'fits and slay the scene bb!

Fit & Features
- Three quarter length sleeves
- Open front
- Sheer mesh
- Plenty of stretch
- Relaxed, comfortable fit
Style Number/Barcode: 06202-0075

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Floral Stunner Tie Front Top
Showcase stunning looks in this sheer floral tie front top! The puff shoulder detailing is so of the moment! Pair with some high rise denim and chic strappy heels.

Fit & Features
- Half length sleeves | Puff shoulders
- V neckline
- Tie front detail
- Cropped
- Sheer crochet floral embroidery on a mesh woven fabric
Style Number/Barcode: 06204-0528

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Chic And Sheer Mesh Kimono
Go for a chic & sheer look by wearing this sheer mesh kimono over your trendy 'fits! The perf spring time layering piece.

Fit & Features
- Short kimono style sleeves
- Tie front belt
- Flowy fit
- Stretchy sheer mesh fabric
Style Number/Barcode: 06204-0424

Category Name: Vacation Looks

Price: $11.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flirty Romance Corset Lace-Up Floral A-Line Mini Dress
The flirty romantic allure of this floral mini dress will take you from brunch and garden party soirees! This mini dress boasts a cinched waist with a corset bodice and head-turning lace-up back design while the a-line silhouette flatters your figure. Pair with ballet flats.

Fit & Features
- Dainty floral print, poplin woven fabrication
- Sweetheart neckline with bust tie, underwire bust
- Adjustable spaghetti straps
- Corset bodice, lace-up back, flexible boning
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3768

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Taking Time To Chill Platform Sandals
Take a moment to chill, look cute, and enjoy some time doin' you! These platform sandals are perfect for those moments! Style with comfy high waist denim, and an over-sized tee!
- Open round toe
- Single band over the toe
- Ankle strap
- Adjustable pin buckle closure
- Faux suede
- Lug sole | Platform
Style Number/Barcode: 07404-0155

Category Name: Vacation Looks

Price: $12.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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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