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.

Tan Lines Cutout Bodycon Mini Dress
Flaunt your figure in this sultry strapless mini dress on vacay or a bach weekend! Designed with cutout accents and stylish hoop inserts, it creates an alluring silhouette that demands attention along the bodycon silhouette.

Fit & Features
- Texture knit stretchy fabric, sewn-in knit lining
- Strapless sweetheart neckline
- Front cutouts and hoop inserts
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000170

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Day At The Hamptons Smocked Linen Pants
Step out and feel luxurious in linen! We are loving this look for resort wear or a day at the beach! Don't forget to pick up the matching top to complete your loook!

Fit & Features
- High waist fit
- Smocked waist line
- Wide fit leg
- Lightweight linen material
- Relaxed fit
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06302-0112

Category Name: Vacation Looks

Price: $13.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Day At The Hamptons Puff Sleeve Top
Step out and feel luxurious in linen! We are loving this look for resort wear or a day at the beach! Don't forget to pick up the matching bottoms to complete your loook!

Fit & Features
- Sweetheart neckline
- Short puff sleeves
- Knotted detail center bust
- Cropped hemline
- Linen material
- Smocked bodice | Moderate stretch
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06001-2458

Category Name: Vacation Looks

Price: $6.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Paper Bag Waist Denim Shorts
You have to get on the paper bag trend this season! These shorts have a faded wash that is so of the moment!

Fit & Features
- High rise elastic banded paper bag waist
- Front drawstring
- Two front and back pockets
- Loose fitting shorts
- Jean fabric | No stretch
Model is 5'4" with a 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
Style Number/Barcode: 06603-0056

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Yes You Can Utility Denim Romper
A motto to live by! " Yes You Can!" and you def can in this cute lil one piece denim romper! Slide on and pair with white sneakers and you're good to go!

Fit & Features
- V-neckline
- Zip front closure
- Short sleeves
- Double breast pockets
- Denim tie mid waist
- Short shorts
- Semi dark denim | Moderate stretch
Style Number/Barcode: 06603-0067

Category Name: Vacation Looks

Price: $15.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Off The Shoulder Button Front Midi Dress
The perf midi dress that has major spring time vibes! With its short puff sleeves, button front detailing, and flowy feel, this dress is a must for your wardobe.

Fit & Features
- Off the shoulder sweetheart neckline
- Short puff sleeves
- Faux button down front
- Stretchy smocked back
- Front slit | Ruffle hem
- Flowy fit
- Woven fabric | Short knit lining
Style Number/Barcode: 05102-0637

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Keep Up Woven Leopard Cropped Blouse
Keep up with that leopard print addiction because its here to stay bae! We are obsessed with this flowy top for the upcoming warmer days! Style with high waist shorts and boots for a total boho vibe!

Fit & Features
- V-neck tie front
- Long flowy balloon sleeves
- Cropped hemline
- Lightweight woven material
- Small leopard print pattern
- Relaxed fit | No stretch
Style Number/Barcode: 06204-0444

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Boho Babe Tie-Front Top
Show up like the boho babe you are in this perf lightweight tie-front top! It features long bishop sleeves, a V-neckline, a tie detail that can be worn in the front or back, and a cropped, form-hugging fit. Wear this top over a bikini or as a cute crop top with some high waist jean shorts!

Fit & Features
- Long bishop sleeves, elastic banded cuffs
- V-neckline
- Tie detail that can be worn in the front or back
- Cropped fit
- Crinkle gauze fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-0442

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish Sweetheart Denim Romper
You're such a stylish sweetheart who will look sooo good in this denim romper!

Fit & Features
- Adjustable spaghetti straps
- Sweetheart neckline
- Bust seam detailing
- Back zipper | Hook and eye closure
- High waist
- Fitted shorts
- Denim fabric | Moderate stretch
Model is 5'4" with a 32" bust, 23" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06603-0066

Category Name: Vacation Looks

Price: $16.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Desert Wanderer Crochet Kimono
We can't wait for festival season! Layer this boho chic crochet kimono over a plain tee and some high waist jean shorts for a look you can wear day to day!

Fit & Features
- Three quarter length flowy sleeves | Angled hems
- Open front
- Flowy, relaxed, and comfortable fit
- Crochet embroidered sheer mesh fabric
- Minimal stretch
Style Number/Barcode: 06204-0278

Category Name: Vacation Looks

Price: $15.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Leopard Print Chiffon Lace-Up Milkmaid Blouse
We love you in a lil' leopard print babe! Keep it light and fresh in a chiffon blouse that practically makes your outfit! Pair with high waist pants and booties for an effortlessly trendy vibe!

Fit & Features
- Square neckline
- Milkmaid design
- Lace-up detailing down the center
- Button detailing at cuffs
- Mid-length hemline
- Sheer chiffon | Lined at the cups
- No stretch
Style Number/Barcode: 06003-0518

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Always Authentic Cropped White Denim Jacket
Keep it real in true denim! Sunny days are coming, and nothing is more flattering than a deep tan and light colored attire! Easily styled with high waist shorts and a graphic tee!

Fit & Features
- Collared neckline
- Silver button closures down the center
- Double breast pockets
- Long sleeves | Cropped raw hemline
- White denim | 100% Cotton | Minimal stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06203-0059

Category Name: Vacation Looks

Price: $12.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
High Rise Light Wash Denim Pants
Keep it chill, keep it casual, and keep a pair of staple denim jeans on the back burner! An obvious closet staple, top with a simple tee, or dress up with ur go-to bodysuit + mules!
Fit & Features
- High rise fit
- Button + zipper closure
- Traditional belt loops + pockets
- Tapered skinny leg
- Comfy stretch | Premium denim
Style Number/Barcode: 06602-0082

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Front Slit Striped Wide Leg Pants
Get totally spring break pairing these striped wide leg pants with some heels and an off the shoulder top!

Fit & Features
- High rise waist
- Tie front belt
- Hidden side zipper | Hook and eye closure
- Flowy wide pant legs | Thigh high front slits
- Striped woven fabric | No stretch
Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06402-0183

Category Name: Vacation Looks

Price: $17.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sassy Sweet Floral Chiffon Ruffled Skater Dress
Sassy and sweet, this floral chiffon skater dress will be your new brunch go-to! The strapless smocked bodice and ruffled skater silhouette are feminine details you'll adore.

Fit & Features
- Chiffon fabric, stretchy knit lining
- Small floral print
- Strapless straight neckline
- Smocked bodice
- High waist seam
- Tiered ruffled design, short skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5967

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
On The Bright Side Puff Sleeve Smocked Jumpsuit
Where are my shades? Girl, you'll be looking so IG-ready in this done-in-one jumpsuit. Add a cute hat and some heels for a picture-perf look!

Fits & Features
- Puff Shoulder Short Sleeves I Ruffle Cuffs
- Elastic Square Neckline With Tie At Center Front
- Smocked Bodice
- Slant Hand Pockets
- Crop, Wide Leg Openings
- Woven Textured Fabric
- Relaxed Fit I 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: 06302-0110

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Paper Bag Tie Waist Jean Skort
The paper bag waist trend is IN right now! Snag this adorable jean skort before it's gone! Pair with a basic tee and some cute wedges for a spring ready look.

Fit & Feautres
- High rise paper bag waist
- Tie front belt
- Hidden front button, zipper, and hook and bar closure
- Slanted front pockets
- Fitted shorts
- Denim fabric | No stretch
Style Number/Barcode: 06603-0068

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sweet As Can Be Mesh Crop Top
Babe, you're as sweet as can be! Get an adorable 'fit by pairing this mesh top with your fave pair of denim!

Fit & Features
- Long sheer puffed sleeves | Elastic banded hems | Swiss dot detailing
- Sweetheart neckline
- Hook and eye front closures
- Sheer smocked mesh back
- Cropped
- All over floral embroidery
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06003-0585

Category Name: Vacation Looks

Price: $14.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Get Twisted Round Ombre Sunglasses
Get twisted this summer, have a lil fun, get a lil shadyyy laddyyyyyy.
- Round sunglasses
- Ombre lenses
- Twisted gold frame
- Skinny arms
Style Number/Barcode: 07008-0687

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Get That Bling Sunglasses
Get that bling bb! These flashy sunnies are a match for you.
- Flat top with gemstone accents
- Thin arms
- Silver frame
- Reflective lenses
- 100% UV protection
Style Number/Barcode: 07008-0701

Category Name: Vacation Looks

Price: $10.90

Availability: Out of Stock
Product Badge:
- Ships Free
Tie-Dye For Side Cut Out Swimsuit
This swimsuit is totes to-die-for! Make a splash at any pool party bb girl

Fits & Features
- One Piece Swimsuit
- Adjustable Spaghetti Straps
- Scoop Neckline I Removable Padded Bust
- Back Hook Closure
- Side Cut-Outs
- Full Coverage Bottoms I High Rise Sides
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0140

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Garden Parties Pleated Midi Dress
Get ready for garden parties, backyard brunches, bridal showers, and spring weddings with this spring staple! Pair with wrap heels, or strappy mules!

Fit & Features
- Tie halter neckline
- Pleated bodice with keyhole cut out
- Smocked stretchy waist line
- Pleated flowy skirt
- Mid-length hemline
- Lightweight sheen polyester material
- Unlined | Moderate stretch
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0724

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
In the Loop Chain Necklace
Serving sleek, chic, and totally on repeat—this one goes with everything. The interlocked design adds texture and edge, perfect for layering or letting it shine on its own.

Fit & Features
- High-shine metal finish
- Interlocked chain-link design
- Back lobster clasp closure with extender
Style Number/Barcode: 07002-000025

Category Name: Vacation Looks

Price: $2.97 $13.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Boho Breeze Tiered Mini Dress
Breeze on by like the boho babe you are in this spring ready mini dress! Paired with some strappy sandals, you'll have the best 'fit.

Fit & Features
- Tank-like shoulder straps
- Square neck and back
- Parital button down front
- Hidden back zipper | Hook and eye closure
- Stretchy smocked waist
- Tiered flowy skirt
- Lightweight woven fabric | Woven skirt lining
Style Number/Barcode: 05102-0626

Category Name: Vacation Looks

Price: $14.97 $36.90

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