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.

Bold Floral Puff Sleeve Catsuit
Bring on the bold florals in this spring ready puff sleeve catsuit! Pair with some wedges and gold jewelry to pull the look together!

Fit & Features
- Short puff sleeves | Elastic banded hems
- Sweetheart neckline
- High waist seam | Tie front detail
- Skinny tapered pant legs
- Floral printed top
- Crepe fabric | Moderate stretch
Style Number/Barcode: 06502-0356

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Daisy Darling Ruched Mini Skirt
Keep it darling in a naturally-inspired daisy print! Pair this pretty mini skirt with a minimal top to let the pattern speak for itself!

Fit & Features
- High Rise Fit
- Daisy Print
- Ruched Drawstring
- Mini Length
- Lined Mesh Fabric
- Form Hugging Fit
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06501-0275

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sleeveless V Neck Waist Cut Out Gauze Knit Romper
Turn to fab rompers with sexy cutouts this season. A romper is a staple piece to take you from festival to date night. This romper features a plunging V-neckline, waist cutouts with elastic ruched bar straps, and a relaxed waist that leads to a pair of wide-leg shorts. The romper is composed of a lightweight gauze fabric that offers a relaxed fit with a slight stretch. Complete look with a denim jacket and fringe earrings.

Fit & Features
- Sleeveless plunging v-neckline
- Waist cutouts with bar straps
- Wide-leg shorts
- Gauze fabric
- Relaxed fit with minimal stretch
Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06303-0040

Category Name: Vacation Looks

Price: $12.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Snake Things Up Wrap Mini Skirt
Shake your everyday look by adding a statement snake print to your neutral palette!

Fits & Features
- High Rise, Elastic Waist
- Decorative Side Tie
- Asymmetrical Wrap Front
- Form-Hugging Fit
- Knit Fabric With All Over Snake Print
- Moderate Stretch
Style Number/Barcode: 06501-0180

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Go With The Flow Kimono Sleeve Top
Go with the flow of this simple yet adorable kimono sleeve top! Wear over your fave mini dress for some extra stylish layers.

Fit & Features
- Three quarter length flowy kimono sleeves
- V neckline
- Tie front detail
- Cropped
- Rayon crinkle woven fabric
- No stretch
Style Number/Barcode: 06204-0401

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Polka Dot Woven Tie Front Top
Channel retro vibes in a polka dot top. This throwback top is giving serious boho vibes, perfect for that next festival. The top features a polka dot design, a tie front bodice and flowy long sleeves with an elastic cuff. The top is composed of a lightweight woven fabric that offers a relaxed fit with slight a stretch. Complete outfit with printed high waist pants or cut off shorts.

Fit & Features
- Plunging tie-front bodice
- Polka dot design
- Long sleeves
- Lightweight woven fabric
- Relaxed fit
- Slight stretch
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small
Style Number/Barcode: 06204-0427

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Effortlessly Chic Ruffle Hem Gauze Crop Top
Effortless chic is the go-to vibe! This crop top is a must for warmer days.

Fit & Features
- Ruffle cap sleeves
- Plunging V neckline
- Elastic banded high waist seam
- Cropped ruffle hem
- Sheer gauze fabric, short front and back lining
- No stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06003-0739

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Tropical Twist Front Short Sleeve Crop Top
Getaway with a tropical crop top. This vacation approved top features a sweetheart neckline, short sleeves, a subtle twist front accent at the center of the bodice, and a cropped hem. The all-over tropical palm leaf print only needs a pair of sunnies and a floppy hat for a picturesque look.

Shop Matching Mini Skirt: Tropical Ruffled Ruched Mini Skirt

Fit & Features
- Sweetheart neckline
- Short sleeves
- Twist front accent at center
- Tropical palm leaf print
- Cropped hem
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
Style Number/Barcode: 06003-1177

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Here's The Twist Lace Romper
You're going to love this! This adorbs lace romper is such an effortlessly chic look. We love pairing this with a hat and some booties

Fits & Features
- Sheer Short Sleeves
- Plunging V Neckline
- Back Zipper With Hook & Eye Closure
- Decorative Twist Detail At Center Front Bodice
- Fitted Shorts
- Fully Lined Lace Overlay Fabric
- Moderate Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06403-0068

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Catch My Sweetness Halter Floral Corset Top
Everyone will catch your sweet vibe in this eyelet floral corset top with a sultry plunge halter neckline and flexible boning that snatches your waist.

Fit & Features
- Floral print, eyelet woven-lined fabric
- Plunge halter neckline, tie-back straps
- Stretchy smocked back
- Flexible boning
- Hidden front hook and eye closures
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06003-000005

Category Name: Vacation Looks

Price: $7.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Long Sleeve Gauze Tie Front Crop Top
Tie up your style with a fab crop top. Head out to that next festival in a chic crop top that features a plunging tie front bodice with a sweetheart bust, a cropped hem, and flowy long sleeves with elastic cuff. The top is composed of a lightweight gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with skinny high waist jeans and sunglasses.

Fit & Features
- Sweetheart neckline
- Tie-front bodice
- Cropped hem
- Long sleeves
- Gauze knit fabric
- Relaxed fit
- Slight stretch
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small
Style Number/Barcode: 06003-0644

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sexy Strappy Back Crop Top
Keep it sassy in this strappy crop top! Step out for a casual night out with the squad in this statement crop top. The top features a flattering scoop neckline, a cropped hem, bungee straps for a secure fit, and strappy back design that adds sexy detail to curves. The top is composed of a faux suede fabric that offers a form hugging fit. Perfect for those warmer days, pair with some high waisted denim cutoffs and dad sneakers!

Fit & Features
- Bungee spaghetti straps
- Strappy back detail
- Scoop neckline
- Cropped
- Faux suede fabric
- Form hugging fit
Mauve Top: Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.

Rust Top: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06001-2519

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cropped Floral Ditsy Puff Sleeve Top
Fall back on a trendy disty crop top. This fab top features a square neckline, short puff sleeves, an all-over ditsy floral print, and a cropped hem. Complete your look with high waist denim and dad sneakers to complete your look!

Fit & Features
- Square neckline
- Short puff sleeves
- Floral dusty print
- Cropped hem
- Lightweight woven fabric
Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06003-0819

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Floral Off The Shoulder Crop Top
Bring on the charm in a floral top. This season must-have features an off the shoulder neckline, an all-over floral print, long sleeves, and a cropped hem. The top is composed of a lightweight woven fabric that offers a relaxed fit. Complete your outfit with high waist shorts and fringe earrings for a casually cute look.

Fit & Features
- Off the shoulder neckline
- Long sleeves
- Floral print
- Cropped hem
- Lightweight woven fabric
Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06003-0882

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Wild West Stitch Tube Top
Channel western vibes in this tube top. Perfect for festival season, this tube top features a western stitch design, a cropped hem, and composed of comfortable knit fabric. Complete your look with a pair of high waist shorts and boots for a country-inspired vibe.

Fit & Features
- Tube top design
- Cropped hem
- Western stitch pattern
- Knit fabric
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06001-2558

Category Name: Vacation Looks

Price: $6.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Time To Hit The Tropics Top
Time to hit the tropics in this paradise-inspired top! Let the pretty floral print transport you to an island paradise. Pair this crop with high waist skinny jeans and strappy heels for a complete look!

Fit & Features
- Sweetheart Neckline
- Short Sleeves
- Tropical Floral Print
- Tie Strap Accent
- Cropped Hem
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06003-0545

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Basic Lace-Up Platform Sneakers
Fall back to basics with sneakers. Lace-up for the day with these basic white sneakers that feature an almond toe, lace-up front, and a wide platform sole. Throw them on with your favorite sets for a complete look.

Fit & Features
- Almond toe
- Lace-up front
- Wide platform sole
Style Number/Barcode: 07407-0045

Category Name: Vacation Looks

Price: $14.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Holographic And Zipper Chunky Sneakers
Give your chunky sneakers a hint of glam. These sneakers mix glam and sport with a holographic glitter accent throughout, a classic lace-up front, rounded toe, and a trendy chunky sole. Standout with the chic zippered accent on the side. Style these glam sneakers with a glitter dress and rhinestone accessories for extra shine.

Fit & Features
- Holographic glitter tonal accent
- Lace-up front
- Round toe
- Chunky sole
- Zipper accent on the side
- Pull tabs
Style Number/Barcode: 07407-0041

Category Name: Vacation Looks

Price: $16.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Pop of Color Chunky Sneakers
Add a pop of color in chunky sneakers. The must-have colorful sporty sneakers feature a round toe, lace-up front, and a chunky sole. Pair these fun sneakers with a set that slays.

Fit & Features
- Bright pastel hue
- Lace-up front
- Round toe
- Chunky sole
Style Number/Barcode: 07407-0034

Category Name: Vacation Looks

Price: $21.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tie Strap Ruched Crop Tank Top
Give your minimal crop tops a ruched twist. Add this staple crop top to your festival and work from home rotation. The minimal crop top features a square neckline, tie-straps, ruched side seams, and a cropped hem. Complete your look with high waist pants that feature a fab bohemian or animal print.

Fit & Features
- Sleeveless square neckline
- Tie-straps
- Ruched side seams
- Cropped hem
- Knit fabric
- Form hugging fit, moderate stretch
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small
Style Number/Barcode: 06001-2648

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Pop of Glam Chunky Bungee Lace Sneakers
Pair glam and sport with chunky sneakers. These fashionista-worthy sneakers feature a round toe, bungee laces with gold-hued D-ring hardware, and a textured chunky rubber sole. Pair these sneakers with leggings and a basic top for an effortlessly put-together look.

Fit & Features
- Round toe
- Bright hue
- Bungee laces
- Gold-hued D-ring hardware
- Chunky textured sole
Style Number/Barcode: 07407-0051

Category Name: Vacation Looks

Price: $13.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Pop of Glam Chunky Bungee Lace Sneakers
Pair glam and sport with chunky sneakers. These fashionista-worthy sneakers feature a round toe, bungee laces with gold-hued D-ring hardware, and a textured chunky rubber sole. Pair these sneakers with leggings and a basic top for an effortlessly put-together look.

Fit & Features
- Round toe
- Bungee laces
- Gold-hued D-ring hardware
- Chunky textured sole
Style Number/Barcode: 07407-0057

Category Name: Vacation Looks

Price: $20.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cropped Brushed Knit Ditsy Tube Top
Keep on trend in a ditsy print top. This floral top features a strapless straight neckline, an all-over ditsy floral print, and a cropped hem. The top is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete your look with high waist jeans and dad sneakers.

Fit & Features
- Straight strapless neckline
- Ditsy floral print
- Cropped hem
- Brushed knit fabric
- Form hugging fit
- Moderate stretch
Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06001-2669

Category Name: Vacation Looks

Price: $6.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Spring Forward Strappy Back Skater Dress
Spring forward in the cutest skater dress showcasing a head-turning strappy tie-back and a flattering ruffled mini-length hem that'll swoon everyone!

Fit & Features
- Woven fabric with woven lining
- Square neckline with bust tie
- Spaghetti straps
- Strappy tie-back design
- Skater silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3687

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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Vacation Looks

HomeVacation Looks

Now Trending

STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials