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.

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
Fun In The Sun Leopard Ribbon Straw Visor
Have a little fun in the sun, but don't forget your visor! So cute with a mini dress, and strappy sandals!
- Open top
- Visor design
- Self tie leopard print ribbon
- Woven straw
Style Number/Barcode: 07302-0202

Category Name: Vacation Looks

Price: $10.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Four Pack Trendy Statement Rings
Step up your jewelry game by accessorizing with these trendy statement rings! Perf for festival season, wear them all together to get that it girl lewk!
- Four pack
- Chain link ring
- Snake-like ring with mini rhinestone embellishments
- Cross ring
- Detailed flexible chain link ring
Style Number/Barcode: 07004-0066

Category Name: Vacation Looks

Price: $6.97 $13.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Charming Finishes Dainty Necklace Set
Adorn your look with layers of dainty finishing touches! This necklace set is the perfect addition to a simple tee & over-sized hat look!
- Set of two necklaces
- One snake chain design
- One four row necklace with star pendant
- Adjustable lobster clasp closure
Style Number/Barcode: 07002-0409

Category Name: Vacation Looks

Price: $6.97 $13.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Gorgeous Getaway Tropical Print Crop Top
This alluring tropical print crop top will create a gorgeous getaway look! Designed with a trendy tropical print pattern on the airy mesh fabric, it features a sleeveless plunging V-neckline, halter spaghetti straps, a tie-front design under the bust, and a cropped, ruffled, babydoll hem with a flowy fit. Style with the matching maxi skirt for your next destination vacay!

Shop Matching Bottoms: Gorgeous Getaway Tropical Print Maxi Skirt

Fit & Features
- Sleeveless plunging V-neckline
- Halter spaghetti straps
- Tie-front design
- Cropped, ruffled, babydoll hem, flowy fit
- Tropical print
- Sheer mesh fabric, knit lining at the bust, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-5074

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Walk On By Jelly T-strap Sandals
Walk on by and show those toes in a flashy way!
- Open almond toe
- Thong strap design
- Rhinestone detailing
- Adjustable pin buckle closure
- Jelly
Style Number/Barcode: 07404-0132

Category Name: Vacation Looks

Price: $9.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Whatever Forever Thin Cat Eye Sunglasses
Not gonna lie, ones you slide on these sunnies you instantly get a lil' sassier. Whatevaaa forevaaa gurrrl. Style with a basic white tee and high waist denim shorts!
- Thin design
- Dark cat eye frame
- Dainty arms
- Dark black lenses
Style Number/Barcode: 07008-0788

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Layer Them On Chain Necklace
Get a layered effect without the work when you style in this baby! Perfect with a simple tee, or even to amp up your work wear!
- Single necklace
- Chain link design
- Side bar detail
- Triple row
- Adjustable lobster clasp closure
- Gold finish
Style Number/Barcode: 07002-0380

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Coast To Coast Beaded Bolo Bracelet 5 Pack
Add a few danty bracelets to your look before you get into your summer travels! This sweet set has a boho vibe with a touch of glam!
- Set of five bracelets
- Bead + Rhinestone detailing
- Adjustable bolo closure
Style Number/Barcode: 07003-0100

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bring It On Wrap Around Rhinestone Belt
Bring on the bling babe! Wrap around rows of rhinestones and make a statement, whether its over your swim look, or for festival you are going to be the center of attention!
- Double row rhinestone detailing
- Chain link design
- Wrap around fit
- Adjustable lobster clasp closure
Style Number/Barcode: 07301-0169

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Time For A Trip Straw Panama Hat
We think that vacay is just around the corner, and what better staple piece to take along than a straw panama hat? Easily style with a linen mini dress, or even flowing pants!
- Panama design
- Woven belt detail
- Composed of a woven straw
- Wide brim
Style Number/Barcode: 07302-0217

Category Name: Vacation Looks

Price: $13.97 $27.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Take Me To Paradise Chain Link Anklet 3 Pack
We are out here so ready for a day of fun in the sun! Style this adorable anklet set with a simple bathing suit and wedges, and get ready for a walk on the beach!
- 3 Pack
- Lobster clasp closure
- Flat chain link design
- Gold finish
Style Number/Barcode: 07003-0090

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Peep The Sparkle 2 Pk Rhinestone Anklet Set
Get a little dazzle going on down to your toes! So cute when you style with a pair of clear heels!
- Set of two anklets
- Double row of rhinestones
- Adjustable lobster clasp closure
Style Number/Barcode: 07003-0089

Category Name: Vacation Looks

Price: $6.97 $13.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Social Butterfly Rhinestone Choker Necklace
Butterfly jewelry is so adorable rn, we can not get enough! Style with matching butterfly earrings for a full vibe!
- Choker style necklace
- Adjustable lobster clasp closure
- Rhinestone embellished butterfly detailing
- Gold chain design
Style Number/Barcode: 07002-0382

Category Name: Vacation Looks

Price: $6.97 $13.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Back At It Hexagon Round Sunglasses
Make a major comeback this summer with a pair of timeless sunniez! Complimenting a simple tee and denim look this pair is a sunny day must have.
- Hexagon edges
- Rounded design
- Dainty gold frame
- Dark lenses
Style Number/Barcode: 07008-0789

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Too Glam Heat Stone Denim Mini Skirt
You'll be just too glam in this heat stone denim mini skirt bby! Pair with some strappy mules and a basic tee to let the skirt be the statement.

Fit & Features
- High rise waist
- Traditional five pocket and belt loop design
- Front button closure
- Front heat stone embellishment
- Short, frayed hem | Form hugging fit
- Distressed denim fabric
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06601-0024

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Smock It To Me Crop Top
Keep it simply smocked for a stylish lewk bb! Pair this closet staple with your fav high waist jeans and sleek heels to make a statement!

Fit & Features
- Sweetheart Neckline
- Spaghetti Tie Straps
- Tie Front Accent
- Smocked Knit Fabric
- Cropped Hem
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06003-0924

Category Name: Vacation Looks

Price: $11.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Crochet All Day Tie Front Crop Top
Slay all day in in trendy crochet in this adorable tie front crop top! Complete your spring time look with a distressed denim mini skirt or boho printed flared pants!

Fit & Features
- Tank-like shoulder straps
- Square neckline | Sheer V detail
- Sheer overall trim | Completely sheer back
- Front lining
- Tie front detail
- Cropped
- Crochet fabric
Style Number/Barcode: 06005-0661

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Blissful View Crochet Knit Midi Skirt
Enjoy stylish bliss in this crochet midi skirt on your next getaway or weekend outing! The skirt offers a flattering high-rise waist, a bodycon fit, and a midi-length hem. Complete the look with the matching halter top.

Shop Matching Top: Blissful View Halter Crochet Crop Top

Fit & Features
- Crochet knit fabric, geometric pattern, knit lining
- High-rise waist, ribbed detail
- Midi-length hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06501-1140

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
On A Roll Tie Waist Shorts
Girl, you'll be on a roll with throwing together outfits in these shorts! Versatile and chic, you can easily pair these with a bodysuit or a tucked-in blouse!

Fits & Features
- Elastic Tie Waist
- Slant Hand Pockets
- Cuffed Leg Openings
- Crepe Fabric
- Moderate Stretch
Style Number/Barcode: 06403-0108

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Floral Chiffon High Low Dress
We're head over heels in love with fab florals! Bring the charm with this pretty high low dress! Pair with a statement heel and neutrals for a soft glam look!

Fit & Features
- V-Neckline | Spaghetti Straps
- Floral Lace Back | Open Lower Back
- Floral Print
- Lined Chiffon Fabric
- High Low Silhouette
- Relaxed Fit
- Minimal Stretch
Style Number/Barcode: 05101-0314

Category Name: Vacation Looks

Price: $17.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Somewhere Far Away Straw Woven Purse
A vacation is way overdue, but once we hit the road, we will be sure to take a staple straw bag along with us! Easily styled with all of your summer gear this straw purse is a sunny day must have!
- Medium circular design
- Crossbody strap
- Woven straw
- Dark tone
- Zipper closure
Style Number/Barcode: 07203-0251

Category Name: Vacation Looks

Price: $13.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tropic Vibes Gold Leaf Earrings
Get into those tropical vibes when you pair these stunning gold leaf earrings with all of your resort wear!
- Rhinestone oval post
- Leaf outline design
- Gold finish
- Post back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged
Style Number/Barcode: 07001-0459

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
An Everyday Look Flat Hoop Earrings
Hoops are an everyday look for sure. They pair well with all looks, and amp up your lazy days!
- Large flat design
- Sleek gold finish
- Omega closure
Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics and lingerie are considered final sale merchandise FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0451

Category Name: Vacation Looks

Price: $3.97 $8.90

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