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.

Point The Way Peep Toe Faux Leather Bootie
Peep that pedi girl in these booties! We love a little peep-toe action, and these booties are all about it! Style with an oversized jean jacket and large hat!

Fit & Features
- Open peep toe
- Ankle fit
- Inner zipper closure
- Block heel
- Faux leather
Style Number/Barcode: 07403-0267

Category Name: Vacation Looks

Price: $12.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Hello Spring Lavender Heeled Mules
Spring forward in a pair of heels that make a statement! Style with a flowy dress, or a pair of cut off denim with a puff sleeve bodysuit
- Open almond toe
- Tall block heel
- Slide on fit
- Single band over the toe
- Faux leather
Please be advised that this style runs 1/2 size small.
Style Number/Barcode: 07401-0665

Category Name: Vacation Looks

Price: $18.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summer Fling Floral Romper
Have some summer fun in this pretty floral romper. Style it with white wedges and a mini bag.

Fits & Features
- Adjustable Spaghetti Straps
- Plunging V Neckline I Button Front Closure
- Zipper Detail At Back
- Wide Leg Openings
- Twist Front Detail
- Front Cutout
Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06503-0084

Category Name: Vacation Looks

Price: $15.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Espadrille Woven Mules
These mules are a summer essential! Pair them with flare pants and a basic crop top.
- Two Bands
- Woven Material
- Open Heel | Square Toe
- Block Heel
Style Number/Barcode: 07401-2269

Category Name: Vacation Looks

Price: $16.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summer Essential Braided Sandals
Keep the summer essentials ready in your closet! A pair of simple pair of sandals is key! Style with a flowy dress or cut off flowy pants!
- Open almond toe
- Thong design
- Dark gold stud detail
- Braided straps
- Adjustable pin buckle closure
- Faux leather
Style Number/Barcode: 07404-0650

Category Name: Vacation Looks

Price: $11.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Straight Chillin' Rhinestone Slides
Get into full relaxation mode when you slip into a pair of slides! And just because you're chillin' doesn't mean you cant add a little glam finish with some rhinestones!
- Open round toe
- Thick band with three rows of rhinestone
- Firm platform sole
- Slide on fit
Style Number/Barcode: 07404-0166

Category Name: Vacation Looks

Price: $9.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Can't Get Enough Platform Simple Sandals
We can't get enough of your look when you top it off with platforms babe! Whether its a summer dress, or denim shorts, you are dressed to impress!
- Open almond toe
- Single band over the toe
- Ankle strap
- Adjustable pin buckle closure
- Firm platform sole
- Faux leather
Style Number/Barcode: 07404-0645

Category Name: Vacation Looks

Price: $12.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Out Of Office Lace-Up Tropical Crop Top
Turn your status to out of office and slip on this tropical crop top for your next weekend getaway or vacation! It flaunts a head-turning strappy lace-up back and a trendy palm print.

Fit & Features
- Tropical palm print, stretchy knit fabric
- Square halter neckline
- Spaghetti straps
- Strappy lace-up back
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000075

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Perfectly Simple Faux Leather Sandals
Having a go-to basic sandals, or two is a definite must! Especially with summer right around the corner boo! Pair with all of your looks for a casual finish!
- Open almond toe
- Single band over the toe
- Firm flat sole
- Ankle strap
- Adjustable pin buckle closure
- Gold hardware
Style Number/Barcode: 07404-0609

Category Name: Vacation Looks

Price: $12.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summer Essential Braided Sandals
Keep the summer essentials ready in your closet! A pair of simple pair of sandals is key! Style with a flowy dress or cut off flowy pants!
- Open almond toe
- Thong design
- Dark gold stud detail
- Braided straps
- Adjustable pin buckle closure
- Faux leather
Style Number/Barcode: 07404-0651

Category Name: Vacation Looks

Price: $11.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Summer Day Eyelet Tie Front Top
We love a little eyelet detailing! This crop top is perf paired with high rise denim shorts and wedges.

Fit & Features
- Eyelet Fabric
- Tie Front
- ¾ Sleeves | Elastic Cuffs
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06204-0555

Category Name: Vacation Looks

Price: $8.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Eyelet Breeze Sleeveless Skater Dress
Spring into the season with this twirl-worthy skater dress! Throw on some pumps and dainty deets to complete a brunch-ready look!

Fit & Features
- V-Neckline
- Spaghetti Straps
- Floral Eyelet Design
- Skater Silhouette
- Lined Lightweight Woven Fabric
- Relaxed Fit
- Minimal Stretch
Style Number/Barcode: 05102-0599

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sunkissed and Stunned Halter Striped Maxi Dress
This striped knit maxi brings the heat with a flirty open back, high front slit, and sheer vibes made for beach strolls or rooftop sips.

Fit & Features
- Striped texture knit design, sheer fabric
- Halter plunge neckline, tie straps
- Open back with tie strap
- High front slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000137

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Hollywood Oversized Sunglasses
Give off celeb vibes in these oversized sunnies! Throw them on with all your bomb summer looks.
- XL Square Plastic Frames
- Ombre Lenses
Style Number/Barcode: 07008-0756

Category Name: Vacation Looks

Price: $5.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Just a Breeze Floral Mini Dress
You can’t go wrong with a floral mini dress! Style it with wedges and hoops for cute and effortless summer look.

Fit & Features
- Off the Shoulder
- Ditsy Floral Print
- Mini Length
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0713

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Hello Summer Straw Tote Bag
Add this straw bag to your collection and get into the summer vibe! Pair it with a sun dress, sandals and oversized sunnies.
- All Over Woven Straw Body
- Circle Handle
Style Number/Barcode: 07203-0295

Category Name: Vacation Looks

Price: $13.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flower Girl Lace Up Crop Top
Girl, you've got that flower power for sure! Pair this adorable ditsy floral crop top with some light wash jeans and strappy mules for a too cute vibe.

Fit & Features
- Off the shoulder square neckline
- Short sleeves
- Lace up front
- Cropped
- Stretchy smocked fabric
- All over ditsy floral print
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06001-2211

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Chill Tie Dye Mini Skirt
Keep it chill but def on trend in this tie dye crop top. Make sure you grab the matching skirt for a fab look!

Fits & Features
- High Waist
- Tie Dye Print
- Matching Crop Top Sold Separately
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06501-0226

Category Name: Vacation Looks

Price: $9.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Such A Flirt Tie Dye Gauze Crop Top
Showcase major flirty vibes in this trendy tie dye crop top! Pair with a distressed denim mini skirt and some strappy sandals for the perf daytime date look!

Fit & Features
- Short puff sleeves
- Sweetheart neckline
- Tie front detail
- Smocked back
- Cropped
- All over multi-colored tie dye print
- Woven gauze fabric
Style Number/Barcode: 06003-0517

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Star Status Gold Link Sunglasses
You’ll look like a star in these oversized sunnies! Pair them with a crop top and denim shorts for a cute summer look.
- Square Frame
- Oversized
- Gold link side detail
Style Number/Barcode: 07008-0713

Category Name: Vacation Looks

Price: $4.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Poised In Petals Floral Chiffon Bodysuit
Look pretty and poised in this flowy bodysuit! Team the look up with a pair of denim skinny jeans or a mini skirt!

Fits & Features
- Surplice Plunging V Neckline With Single Snap Button Closure
- Roomy Sheer Long Sleeves I Elastic Cuffs
- Thong Bottom With Dual Snap Button Closure
- Chiffon Fabric I Lined At The Front Bodice
- Relax Fit I Minimal Stretch
Style Number/Barcode: 06003-0578

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
High Waist Distressed Denim Shorts
Go for those girl next door vibes with classic denim shorts for a laid-back look!

Fit & Features
- High Rise Waist
- Single Button and Zipper Closure
- Traditional Five Pocket and Belt Loop Design
- Heavy Distressed Detailing
- Frayed Hem
- Light Medium Wash Denim Fabric
- Relaxed Fit | Minimal Stretch
Medium Denim: Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06603-0078

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Always Happy Hour High-Rise Slit Midi Skirt
Embrace the sultry vibes of this high-rise slit midi skirt for your next happy hour spree! Pair with the matching top to complete the vibe.

Shop Matching Top: Always Happy Hour Cowl Neck Crop Top

Fit & Features
- Double-lined slinky knit stretchy fabric
- High-rise waist
- Side slit
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06501-000044

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
High Waist Distressed Denim Pants
Your new fave pair of denim - trust us! Add to cart for a trendy 'fit.

Fit & Features
- High rise waist
- Traditional five pocket and belt loop design
- Front button | Hidden zipper closure
- Destructed detailing
- Frayed hem
- Denim fabric | No stretch
Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06602-0078

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

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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