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.

Diva Vibes Cat-Eye Sunglasses
Bring the diva vibes to your look with these stylish sunglasses! They feature an oversized square cat-eye design with a tortoise-shell print. Pair these shades with a chic crossbody purse.

Fit & Features
- Oversized square cat-eye design
- Tortoise-shell print
- Plastic frame
Style Number/Barcode: 07008-0833

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Babe Sleeveless Midi Dress
Hey babe, show off your adorable style in this floral midi dress that is perf for spring. It features a sleeveless square neckline, thin ruffle shoulder straps, a fitted bodice, and a flowy mid-length silhouette with a thigh-high slit. Complete the look with hoop earrings and strappy sandals.

Fit & Features
- Sleeveless square neckline
- Thin ruffle shoulder straps
- Fitted bodice
- Flowy mid-length silhouette
- High front slit
- Ditsy floral print
- Knit fabric
- Runs true to size
Style Number/Barcode: 05102-0741

Category Name: Vacation Looks

Price: $20.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Such A Sweetheart Lace Mini Dress
Keep it sweet and stylish with a mini dress that features gorge details! The dress features a sweetheart neckline, short sleeves, a floral lace body, and a mini-length silhouette. The dress offers a form-hugging fit. Complete look with wedges and charm necklaces.

Fit & Features
- Sweetheart neckline
- Padded cups, underwire
- Short sleeves
- Floral lace body
- Mini length silhouette
- Form hugging fit
- Runs true to size
Style Number/Barcode: 05101-0963

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Take It Easy Straw Fanny Pack Belt
Take it easy with a cute fanny pack belt to carry all your essentials with you! The belt features a faux leather band and an attached small straw fanny pack with fold-over closure. Complete look with neutral-hued pants for that seamless look.

Fit & Features
- Faux leather band
- Attached fanny pack with fold-over closure
- Straw
Style Number/Barcode: 07203-0568

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Glam Trendsetter Four-Pack Necklace Set
Bring the bling to your look with this trendy necklace set. It features four necklaces, the shortest layer a dainty chain with a center script charm that reads "Babygirl," and the second layer a thick twisted chain. The third necklace has a center rhinestone adorned cross charm, and the fourth necklace has a center rectangular-shaped charm. Pair all of these necklaces together with a basic tee and denim for a cool look.

Fit & Features
- Four-pack necklace set
- Layered design
- Script charm that reads "Babygirl"
- Twisted chain
- Rhinestone cross charm
- Rectangular-shaped charm
- Adjustable lobster clasp closures
Style Number/Barcode: 07002-0708

Category Name: Vacation Looks

Price: $0.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dainty Lace Ruched Mesh Mini Dress
Make hearts flutter in this gorgeous dainty lace and mesh mini dress. It features a sleeveless bodice, adjustable spaghetti straps, a V neckline with a sheer lace ruffle trim, all-over ruched detailing, and a short, curve-hugging silhouette with a front drawstring and a sheer lace ruffle hem. The dress is composed of a sheer mesh fabric with floral lace details and a full knit lining. Complete your look with duster earrings and cute wedges.

Fit & Features
- Adjustable spaghetti straps
- V neckline with a sheer lace ruffle trim
- Ruched detailing
- Mini-length, form-fitting style
- Front drawstring and sheer lace ruffle hem
- Sheer mesh fabric with floral lace details and a full knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05101-0955

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Effortlessly Stunning Crochet Waist Maxi Dress
You'll look effortlessly stunning in this flowy maxi dress that is perfect for the warmer months. It features spaghetti straps that lead to a cross-back design, a lace top with a V neckline, a sheer crochet high waist, and a flowy floor-length gauze skirt with a side slit. Complete the look with on-trend wedges.

Fit & Features
- Spaghetti straps
- Cross back design
- Lace top, V neckline
- Sheer crochet high waist
- Floor-length gauze skirt, side slit
- Flowy silhouette
- Runs true to size
Style Number/Barcode: 05102-0754

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flirty And Floral High Low Chiffon Kimono
Play up your sweet side with a kimono that is perfect to layer over your looks. The kimono features a draped open front, long sleeves, a floral print, and a flowy high-low silhouette. The kimono is composed of a sheer chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with a mini dress and wedges.

Fit & Features
- Draped open front
- Long sleeves
- Floral print
- High-low silhouette
- Sheer chiffon fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-0806

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ready To Vacay Bikini Top
Start those vacay vibes with a bikini top that will have you ready to bask in the sun! The top features a halter neck with neck ties, a sexy square cut out at the bodice, and back ties. Complete look with the matching bikini bottoms and sunnies for that weekend getaway!

Shop Matching Bikini Bottoms: Ready To Vacay Bikini Bottoms

Fit & Features
- Halter neck
- Bandeau-styled bodice
- Square-shaped cutout
- Back ties
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 07104-0653

Category Name: Vacation Looks

Price: $4.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Breezy Babe High-Rise Slit Maxi Skirt
From farmer's market to the beach, this flowy maxi skirt is ready to create stylish looks for any adventure! With a flattering high-rise waist, a flirty front slit, and a tiered silhouette, this skirt is essential for spring to summer.

Fit & Features
- Chambray woven fabric
- High-rise waist
- Front slit
- Tiered flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06301-0208

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
High-Rise Button-Up Cutoff Denim Shorts
Refresh your wardrobe with these cutoff denim shorts that are perf for warm weather! They feature a high-rise waist, a traditional five-pocket and belt loop design, a button-up front, and a frayed, cutoff hem. Pair these shorts with a floral crop top and strappy sandals.

Fit & Features
- High-rise waist
- Traditional five-pocket and belt loop design
- Button-up front
- Frayed, cutoff hem
- Distressed details
- Denim fabric
- Runs true to size
Style Number/Barcode: 06603-0154

Category Name: Vacation Looks

Price: $15.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Quilted Glamour Double Buckle Sandals
Bring the glam with sandals that make a chic statement! The sandals feature an adjustable ankle strap, a diamond quilted body, a double row of buckled straps, an open almond toe, and a textured sole. Complete look with a blouse and cutoff shorts to finish off your look!

Fit & Features
- Adjustable ankle strap
- Diamond quilted body
- Double row of buckled straps
- Open almond toe
- Textured sole
Style Number/Barcode: 07404-0673

Category Name: Vacation Looks

Price: $12.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweet And Flirty Floral Tie-Front Top
Bring the sweet and flirty vibes to your springtime look with this adorable floral top! It features long dramatic bell sleeves with crochet trim details, a V neckline, a tie-front, and a cropped fit. Complete the outfit with high-rise denim shorts and strappy sandals.

Fit & Features
- Long flowy bell sleeves with crochet trim details
- V neckline
- Tie-front
- Cropped
- Floral chiffon fabric
- Runs true to size
Style Number/Barcode: 06204-0815

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Total Sweetheart Floral Mini Dress
Showcase your sweet style in this adorable floral printed mini dress! It features short sleeves, a V neckline, ruching at the bust with a front drawstring, a small cutout under the bust, and a short, form-hugging silhouette. The unlined knit fabric offers plenty of stretch. Complete your look with dainty earrings and a cute crossbody purse.

Fit & Features
- Short sleeves
- V neckline
- Ruching at the bust with a front drawstring
- Small cutout under the bust
- Ruching down the sides
- Mini-length, form-hugging fit
- Unlined knit fabric with plenty of stretch
- Floral print
- Runs true to size
Style Number/Barcode: 05102-0679

Category Name: Vacation Looks

Price: $9.97 $31.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet And Flirty Floral Tie-Front Top
Get a sweet and flirty look in this adorable tie-front top. It features long blouson sleeves, a V neckline, a tie-front, and a cropped fit. The semi-sheer chiffon fabric has an all-over floral print, making the top a perf option for a daytime date. Complete your outfit with a denim mini skirt and sandals.

Fit & Features
- Long blouson sleeves with cinched hems
- V neckline
- Tie-front
- Cropped
- Semi-sheer chiffon fabric
- Floral print
- Runs true to size
Style Number/Barcode: 06204-0832

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Honey Charm Layered Chain Link Necklace
Layer on the style with a stylish necklace that keeps your look on-point! The necklace features a seven-row layer of a mix of dainty and chunky chain links, a honey script charm, and a lobster clasp closure. Complete look with a crop top and skinny jeans.

Fit & Features
- Seven-row layer
- Dainty chain link
- Chunky chain link
- Honey script
- Lobster clasp closure
Style Number/Barcode: 07002-0718

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Too Chic Ruffled Eyelet Mini Dress
You'll be looking too chic with a mini dress that brings all those cute deets! The dress features an elastic square neckline, short puff sleeves, a lace-up front, an eyelet design, and a mini-length silhouette with a ruffled hem. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.

Fit & Features
- Elastic square neckline, puff short sleeves
- Front lace-up
- Form-fitting, mini-length, ruffle hem
- Eyelet lace fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-1163

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
What A Catch Fishnet Bikini Top
You'll be looking like a cute catch with this bikini top! The top features triangle cups, a halter neck tie, back ties, and a fishnet overlay. Complete the look with the matching bikini bottoms and sunnies.

Shop Matching Bikini Bottoms: What A Catch Fishnet Bikini Bottoms

Fit & Features
- Triangle-shaped cups, removable padding
- Halter neck ties
- Back ties
- Fishnet overlay
- Form hugging fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0542

Category Name: Vacation Looks

Price: $5.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Flutter Sleeve Chiffon High-Low Duster
Layer on this floral chiffon duster for a cute picnic date or sunset stroll. It features short flutter sleeves, a V neckline, a high waist with a stretchy smocked back, front button details, and a flowy, high-low fit. The sheer and airy chiffon fabric showcases an all-over floral print for a pretty vibe. Complete your outfit with a casual dress and strappy sandals.

Fit & Features
- Short flutter sleeves
- V neckline
- High waist with a stretchy smocked back
- Front buttons
- Flowy, high-low silhouette
- Sheer floral chiffon fabric
- No stretch
Style Number/Barcode: 06204-0797

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Retro Babe Sleeveless Denim Jumpsuit
Channel a retro vibe with a jumpsuit that brings the flare to your look! The jumpsuit features a sleeveless scoop neckline, a zippered front, tank straps, a tie waist belt with belt loops, side pockets, and a straight leg with flared hem. Complete look with wedges.

Fit & Features
- Sleeveless scoop neckline
- Zippered front
- Tank shoulder straps
- Tie waist belt with belt loops
- Side pockets
- Straight leg with a flared hem
- Form hugging fit runs true to size
Style Number/Barcode: 06602-0219

Category Name: Vacation Looks

Price: $6.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Smocked Tie-Front Tube Top
Give your look a fab twist with a cute tube top to pair with your favorite high waist bottoms. The tube top features a strapless sweetheart neckline, a twist-front accent, a cropped hem, and is composed of a smocked knit fabric. Complete the look with a denim skirt and wedges.

Fit & Features
- Strapless sweetheart neckline
- Tie-front accent
- Cropped hem
- Smocked knit fabric
- Form-hugging fit
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-3163

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Lace-Up Sleek PVC Sandals
Lace-up in cute sandals that keep your look sleek and stylish. The sandals feature lace-up straps, a closed back, an open square toe, and a clear PVC strap over the toe. The sandals are composed of a faux leather material. Complete look with a floral romper.

Fit & Features
- Lace-up straps
- Open square toe
- Clear PVC strap over the toe
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-0739

Category Name: Vacation Looks

Price: $12.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Vibes Mesh Headwrap
Channel those chic vibes with a headwrap that keeps tresses relaxed and stylish. The headwrap is composed of mesh fabric and has an oversized-fit wrap-around design. Complete your look with the matching swim coverup and a cute two-piece swimsuit for a fab day out!

Shop Matching Swim Coverup: Cinched and Chic Mesh Swim Coverup

Fit & Features
- Wrap-around design
- Mesh material
Style Number/Barcode: 07305-0276

Category Name: Vacation Looks

Price: $3.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Iconic Style High-Rise Cut-Off Denim Shorts
These iconic denim shorts will forever be a flattering staple in your closet! The high-rise waist provides a flattering and comfortable fit, while the frayed hem adds a touch of edginess.

Fit & Features
- Medium wash denim, non-stretch
- High-rise waist
- Frayed hem
- Front five-button fly closures
- Five-pocket styling, belt loop accents
- Runs true to size
Style Number/Barcode: 06603-000001

Category Name: Vacation Looks

Price: $9.97 $34.90

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