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.

Floral Dream Tie Front Top
You'll like a total dream in gorgeous florals in this tie front top! The lightweight fabric makes it perf for spring and summer!

Fit & Features
- Long billowy sleeves | Elastic banded cuffs
- Deep V neckline
- Tie front detail
- Woven fabric | No stretch
- All over floral print
Style Number/Barcode: 06204-0523

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Boho Baby Crochet Cropped Top
Whether you are getting festival ready, or you are planning your vacay wardrobe, we are lovin' this set 4 u! Don't forget to pick up the matching fringe skirt, and throw on a panama hat for a pic-worthy moment!

Shop Matching Bottoms: Boho Baby Crochet Fringe Skirt

Fit & Features
- Scoop neckline
- Long sleeves
- Cropped hemline
- Crochet | Moderate stretch
- Sheer
Style Number/Barcode: 06005-0363

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Boho Baby Crochet Fringe Skirt
Whether you are getting festival ready, or you are planning your vacay wardrobe, we are lovin' this set 4 u! Don't forget to pick up the matching cropped top, and throw on a panama hat for a pic-worthy moment!

Shop Matching Top: Boho Baby Crochet Cropped Top

Fit & Features
- High waist fit | Elastic stretch waist band
- Long hemline
- Fringe trim
- Crochet | Moderate stretch
- Sheer
Style Number/Barcode: 06501-0165

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Feelin' Boho Halter Open Back Knit Top
Create a boho babe vibe in this sleeveless knit top with a plunging halter neckline, open back, and a trendy front crochet flyaway design. Style with the matching hot shorts for festival season!

Shop Matching Bottoms: Feelin' Boho Scallop Hem Knit Hot Shorts

Fit & Features
- Sweater knit fabric
- Sleeveless plunge halter neckline, tie-back straps
- Open back, lower tie-back straps
- Front crochet flyaway design
- Mid-length hem, flowy fit
- Runs true to size
Style Number/Barcode: 06005-2256

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Classic Cutie Chiffon Lace Back Crop Top
Okay cutie! We are lovin' this chic and sweet crop top on you! Don't forget to add the matching skirt to cart ;-)

Shop Matching Bottoms: Classic Cutie Chiffon Maxi Skirt

Fits & Features
- Adjustable Spaghetti Straps I T-Back Design
- V Neckline
- Lace Back I Zipper Closure
- Crop Hemline
- Chiffon Lined Fabric
- Minimal Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 06003-0537

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Time Off Puff Sleeve Linen Crop Top
Reset and recharge bb girl! Treat yourself to some time off and escape to a resort! You're going to need a cute linen set for that trip

Shop Matching Bottoms: Time Off Linen High Waist Wide Leg Pants

Fits & Features
- Short Puff Sleeves
- Elastic Cuffs, Shoulders & Square Back Neckline
- V Neckline I Adjustable Tie Front
- Crop Hemline
- Cotton Blend Linen Fabric
- Moderate Stretch
- Matching Bottoms Sold Separately
Style Number/Barcode: 06003-0875

Category Name: Vacation Looks

Price: $6.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Fresh And Floral Mesh Duster
Get a fresh look, perf for the warmer months, with this gorg lightweight sheer floral duster! Pair with a simple tank and some distressed denim shorts!

Fit & Features
- Three quarter length loose sleeves | Elastic banded hems
- Drape open front
- Flowy, comfortable fit
- Sheer floral printed mesh fabric
- Plenty of stretch
Style Number/Barcode: 06202-0077

Category Name: Vacation Looks

Price: $10.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Lulu High Waist Distressed Shorts
Oasis by Eunina

Keep it casual and laid back in high waist shorts! Pair this perfectly with a sassy crop top to keep the good times going!

Fit & Features
- High Rise Waist
- Single Button and Zipper Closure
- Traditional Five Pocket and Belt Loop Design
- Distressed Cut-Off Hem
- Light-Medium Wash
- Relaxed Fit
- Moderate Stretch
Style Number/Barcode: 06603-0034

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Super Distressed Denim Mini Skirt
Everyone needs a distressed denim mini in thier closet! Pair the skirt with a plain white tee and some cute sneakers for a laid back, casual vibe.

Fit & Features
- High rise waist
- Traditional five pocket and belt loop design
- Front button and hidden zipper closure
- Major destructued detailing
- Short frayed hem
- Denim fabric | Moderate stretch
Style Number/Barcode: 06601-0012

Category Name: Vacation Looks

Price: $11.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Feelin' Sassy Satin Crop Top
You'll be feelin' a little sassy and a whole lot stylish in this chic satin crop top! Pair with some distressed denim for a perf everyday trendy look.

Fit & Features
- Short puff sleeves
- Sweeheart neckline
- Tie front detail
- Majorly cropped
- Satin-like fabric | No stretch
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-0607

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flowy Floral Chiffon Crop Top
Get all those flowy floral feels in this lightweight chiffon crop top! A major spring time vibe for sure.

Fit & Features
- Elastic banded off the shoulder neckline
- Long loose sleeves | Elastic banded cuffs
- Cropped elastic banded hem
- Sheer chiffon fabric
- All over floral print
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-0655

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
High Rise Tie Waist Skinny Pants
These high rise tie waist skinny pants are so wearable! Dress them up with a pretty blouse and some heels for the office, or with a graphic tee and some booties for happy hour!

Fit & Features
- High rise waist
- Tie front detail
- Skinny pant legs
- Stretchy knit fabric
- Form hugging fit
Style Number/Barcode: 06502-0343

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Major Babe In Denim Shorts
Hey girl! You'll be such a major babe in these belted denim shorts! Pair with a classic tank and some heels for a simple style!

Fit & Features
- High rise distressed waist | Elastic banded back
- Included belt | Double D ring buckle
- Two front pockets | Two faux back pockets
- Cuffed hems
- Denim fabric | No stretch
Style Number/Barcode: 06603-0084

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Give It A Spin Off Shoulder Pleated Skater Dress
Look chic and cute in this twirl-worthy skater dress! Her best features are def the hidden hand pockets Make sure you get a pair of block heels to complement this dress!

Fits & Features
- Dual Off Shoulder Bar Straps
- V Neckline I Elastic Square Back
- Hidden Hand Pockets
- Mini Length Silhouette I Pleated Skirt I Skater Silhouette
- Crepe Fabric
- Form Hugging Fit I Moderate Stretch
- Zipper Not Featured
Style Number/Barcode: 05101-0783

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Caralisa Floral Chiffon High Slit Dress
Special Occasion

Crafted from light chiffon, a scatter of floral and botanical prints deck out our lovely Caralisa. Her roomy long sleeves and airy chiffon skirt add on a layer of dreaminess to this utterly romantic dress. Slip into Caralisa for that spring wedding you've RSVP'ed to!

Fits & Features
- Unlined, Plunging Surplice V Neckline
- Tie Waist
- Sheer Long Sleeves With Gold-Tone Buttoned Cuffs
- Floor Length Hem I Thigh-High Slit
- Lined Chiffon Fabric
- Relaxed Fit I Moderate Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-0809

Category Name: Vacation Looks

Price: $29.97 $69.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Boost Of Confidence Fringe Suede Saddle Purse
Need a little confidence boost? We got u boo! This stunning fringe bag will have you feeling some sort of way when all that fringe swinging with every step!
- Large saddle bag design
- Rhinestone suede dangling fringe
- Fold over snap closure
- Crossbody shoulder strap
- Micro suede
- Inner zipper pocket
Style Number/Barcode: 07203-0237

Category Name: Vacation Looks

Price: $13.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Falling For Charm Strappy Open Back Floral Mini Dress
Fall for the charm of this flirty floral mini dress with a head-turning strappy open back and A-line fit perfect for showing off at brunch or a spring date!

Fit & Features
- Floral print, stretchy knit fabric
- Halter V-neckline, spaghetti strap tie
- Open back, strappy spaghetti strap ties
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6042

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweeten The Deal Eyelet Tie Front Top
Sweeten your look with this charming tie front crop top! Wear this with your fave denim cut-offs or over a tube top!

Fits & Features
- Plunging V Neckline
- Tie Front Design
- Long Sleeves I Elastic Cuffs
- Woven Fabric I Eyelet Design Throughout
- Moderate Stretch
Style Number/Barcode: 06202-0082

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Under The Sun Tropical Slit Maxi Skirt
Perfect for any vacation or resort escape, this tropical maxi skirt boasts a sultry high front slit and a flowy silhouette for a breezy allure. Pair with the matching top.

Fit & Features
- Tropical print, stretchy knit fabric, knit panty lining
- Low-rise waist
- High front slit
- Flowy silhouette
- Maxi-length hem
- Runs true to size
Shop The Matching Top: Under The Sun Tropical Tie-Front Crop Top
Style Number/Barcode: 06501-000014

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Drawn to Florals Crop Top
Get drawn to this sweet trend as you let your beauty bloom in florals! Pair this pretty crop top with high waist pants and wedges for the perfect spring look!

Fit & Features
- Square Neckline
- Smocked Bodice | Drawstring Accent
- Long Sleeves | Smocked Cuffs
- Floral Print
- Sheer Chiffon and Smocked Knit Fabric
- Cropped Hem
- Relaxed Fit | Moderate Stretch
Natural Style Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06003-0675

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tortoise O-Ring Ribbed Knit Midi Dress
Casual and cute, you'll be loving the O-ring belt around this chic midi dress! We love to see you rockin' this with some white sneakers and a faux leather jacket!

Fits & Features
- Spaghetti Straps
- Scoop Neckline I Square Back
- Tortoise O-Ring Waist Belt
- Midi Length Silhouette
- Ribbed Knit Fabric I Fully Lined
- Form Hugging Fit I Plenty Of Stretch
- Zipper Not Featured
Style Number/Barcode: 05102-0673

Category Name: Vacation Looks

Price: $13.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Button Up In Denim Frayed Dress
Button up in this denim dress to make a fun statement bby!

Fit & Features
- Collared Neckline
- Small Chest Pockets | Button Down Front
- Short Sleeves
- Zipper Front Closure | Side Pockets
- Frayed Hem
- Medium Wash Denim
- Relaxed Fit | Slight Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0436

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Western Vibes Braided Panama Hat
Get those western vibes goin' when you style a suede panama hat with your muscle tee, high waist denim & cowboy fringe boots!
- Western style panama hat
- Braided detailing with silver conchos
- Faux suede
- Non-stiff brim
Style Number/Barcode: 07302-0198

Category Name: Vacation Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Two Pack Chain Link Necklaces
Layer on this set of chain necklaces to amp up your trendy festival lewk babe!
- Two pack
- Snake chain with dainty rhinestone charm
- Chain link choker
- Adjustable lobster clasp closures
Style Number/Barcode: 07002-0384

Category Name: Vacation Looks

Price: $5.97 $12.90

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