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.

Tropical Paradise Smocked Tube Top
Transport to paradise with a smocked tube top that is too fab! The top features a sleeveless sweetheart neckline, ruffled trim, tie-front accent, a tropical palm leaf print, and a smocked body. Complete the look with the matching mini skirt.

Shop Matching Mini Skirt: Tropical Paradise Smocked Mini Skirt

Fit & Features
- Sleeveless sweetheart neckline
- Ruffled trim
- Tie-front accent
- Tropical palm leaf
- Smoked body
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06003-1316

Category Name: Vacation Looks

Price: $4.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tropical Paradise Smocked Mini Skirt
Transport to paradise with a smocked mini skirt that is too fab! The skirt features a high-rise waist, a tropical palm leaf print, and a smocked body. Complete the look with the matching tube top.

Shop Matching Tube Top: Tropical Paradise Smocked Tube Top

Fit & Features
- High rise waist
- Tropical palm leaf
- Smocked body
- Mini length silhouette
- Form hugging fit, moderate stretch
Style Number/Barcode: 06301-0081

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Crochet Cutie Triangle Crop Top
Live out your boho dreams in this cute crochet crop top! It features thin halter straps that tie at the back of the neck, a triangle design with a V neckline, an open back, lower tie back straps, and a cropped, form-fitting style. The crochet fabric has no stretch and showcases a dainty cutout design along the trim. The thin straps feature adorable tassel details. Pair this top with the matching skirt and a trendy layered necklace.

Shop Matching Mini Skirt: Crochet Cutie Mini Skirt

Fit & Features
- Sleeveless bodice
- Thin halter straps that tie at the back of the neck
- Triangle design with a V neckline
- Open back with lower tie back straps
- Cropped, form-hugging fit
- Crochet fabric with no stretch
- Runs true to size
Style Number/Barcode: 06005-0909

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chain Link Necklace Two Pack
Layer on the style with a variety of necklaces that take your look to the next level! The multi-pack features an assortment of two chain-link necklaces that differ in length. Complete look a romper and wedges.

Fit & Features
- Includes two necklaces
- Chain-link
- Various lengths
- Lobster clasp closure
Style Number/Barcode: 07002-0743

Category Name: Vacation Looks

Price: $4.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Laid Back Glamour Crochet Knit Midi Dress
Keep it effortlessly glam with a crochet-knit dress! The dress features a sleeveless V-neckline, a mini side slit, and a midi length silhouette. The dress is composed of a crochet knit fabric that offers a relaxed fit with a moderate stretch. Complete look with wedges.

Fit & Features
- Sleeveless V-neckline
- Mini side slit
- Midi length silhouette
- Crochet knit fabric
- Relaxed fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0674

Category Name: Vacation Looks

Price: $15.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
All Eyes On Me Puff Sleeve Romper
All eyes will be on you in this cute romper! The romper features a sleeveless V-neckline, short puff sleeves, a keyhole at the back with tie-up straps, and wide-leg shorts. Complete the look with wedges and a dainty necklace.

Fit & Features
- Surplice V-neckline
- Short puff sleeves, elastic cinched hems
- Keyhole at the back, back zipper and hook and eye closure
- Tie-up straps at back
- Wide leg shorts
- Denim knit fabric, no stretch, form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-0198

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Take Me Back Tropical Maxi Dress
Get taken back to that dream vacay with a fab maxi dress! The dress features a sleeveless V-neckline, adjustable spaghetti straps that cross at the back, a tropical print, an open back, a smocked waist, and a flowy maxi length silhouette. Complete with wedges.

Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross at back
- Tropical print
- Open back
- Smocked waist
- Maxi length silhouette
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05101-0572

Category Name: Vacation Looks

Price: $6.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Own The Moment Tube Floral Maxi Dress
Ready to shut down the vacation pics? This strapless floral maxi dress brings effortless chic with a curve-hugging fit and leg-baring side slit.

Fit & Features
- Floral print, mesh-lined fabric, moderate stretch
- Strapless tube neckline
- High side slit
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000237

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Take A Twirl Chiffon Skater Dress
Take a twirl in this pretty skate dress that is perf for your special milestones! The dress features a sleeveless wrap V-neckline, a double row of adjustable spaghetti straps, and a skater silhouette. The dress is composed of a lined chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with heels.

Fit & Features
- Sleeveless wrap V-neckline
- Double row spaghetti straps
- Skater silhouette
- Lined chiffon fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-0827

Category Name: Vacation Looks

Price: $19.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bohemian Beat Smocked Tube Top
Step out this season with a boho tube top that brings those wanderlust vibes! The top features a sleeveless square neckline, a bohemian print, and composed of a smocked fabric. Shop matching maxi skirt.

Shop Matching Maxi Skirt: Bohemian Beat High Waist Maxi Skirt

Fit& Features
- Sleeveless square neckline
- Bohemian print
- Smocked knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06003-1318

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bohemian Beat High Waist Maxi Skirt
Step out this season with a boho maxi skirt that brings those wanderlust vibes! The skirt features a high-rise waist, a bohemian print, a high side slit, and a maxi length silhouette. Complete look with the matching tube top.

Shop Matching Tube Top: Bohemian Beat Smocked Tube Top

Fit & Features
- High rise waist
- Bohemian print
- High side slit
- Maxi length silhouette
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06301-0086

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Casual-Chic Strappy Sandals
These braided detail strappy sandals will be a chic addition to your casual summer outfits. They feature an open round toe, a thin braided strappy design, an adjustable ankle strap, and a flat sole. Style these sandals with a basic tee and denim shorts.

Fit & Features
- Open round toe
- Braided strappy design
- Adjustable ankle strap, buckle detail
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-0858

Category Name: Vacation Looks

Price: $12.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Weekend-Ready Platform Sandals
Get totally weekend-ready with these on-trend platform sandals! They feature an open round toe, a toe strap, an adjustable ankle strap, and a stacked platform. Style the sandals with a floral dress.

Fit & Features
- Open round toe
- Toe strap
- Adjustable ankle strap, buckle detail
- Stacked platform
- Faux leather straps
- Runs true to size
Style Number/Barcode: 07404-0868

Category Name: Vacation Looks

Price: $7.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summertime Glam Thong Sandals
Bring the glam to your summertime looks with these embellished sandals. They feature an open round toe, a thong strap design with rhinestone detailing, a rhinestone trim, and a flat sole. Style these sandals with a cute bikini and oversized sunnies for a perf poolside outfit.

Fit & Features
- Open round toe
- Thong strap design, rhinestone embellishment
- Rhinestone trim
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-0879

Category Name: Vacation Looks

Price: $10.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Pretty Petal Perfection Maxi Dress
Showcase your beauty in this perfect floral maxi dress. It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back design, ruched detailing, and a flowy floor-length silhouette with a thigh-high side slit. The floral printed sheer mesh fabric includes a short lining. Style this dress with classic block heels.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps, cross-back design
- Ruching
- Flowy floor-length silhouette
- High side slit
- Floral printed sheer mesh fabric, short lining
- Runs true to size
Style Number/Barcode: 05101-0968

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Glam It Up Rhinestone Belly Chain
Glam up your poolside look with this trendy belly chain! It features a dainty chain with a rhinestone drop design and an adjustable lobster clasp closure. Style it with your fave swimsuit and chic shades for the perf pool party look.

Fit & Features
- Dainty chain
- Rhinestone drop design
- Adjustable lobster clasp closure
Style Number/Barcode: 07002-0731

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Vacay Bound Tie-Front Top
Don't forget to pack this adorable tie-front top for your next summer vacay! It features long bishop sleeves, a deep V-neckline, a cute tie-front, and a cropped fit. The chiffon fabric has an all-over tropical floral print that would pair perfectly with denim shorts. Complete the look with tassel earrings.

Fit & Features
- Long bishop sleeves, cinched hems
- Deep V-neckline
- Tie-front
- Cropped fit
- Chiffon fabric, tropical floral print
- Runs true to size
Style Number/Barcode: 06204-0857

Category Name: Vacation Looks

Price: $12.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish Moves Eyelet Mini Dress
Make some seriously stylish moves with this mini dress! The dress features a square neckline, short puff sleeves, an eyelet design, an open back with tie-back straps, and a mini-length silhouette. Complete look with wedges.

Fit & Features
- Square neckline
- Short puff sleeves
- Eyelet design
- Open back with tie back straps
- Mini length silhouette
- Form hugging fit
- Runs true to size
Style Number/Barcode: 05101-1003

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Floral Frenzy Off The Shoulder Skater Dress
Start a frenzy with a floral dress that brings the romance! The dress features an off-the-shoulder neckline with a sweetheart bust, quarter-length short sleeves, a floral print, and a skater-length silhouette. Complete look with wedges and a floppy hat.

Fit & Features
- Off the shoulder neckline
- Sweetheart bust
- Quarter-length short sleeves
- Floral print
- Skater length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4179

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Gorgeous Goddess Metallic Mini Dress
You'll look like a total gorgeous goddess in this sultry metallic mini dress! It features a sleeveless V-neckline, thin shoulder straps, a backless design, a mini-length, curve-hugging silhouette, and a metallic sweater knit fabric with center seam detailing down the front. Style this dress with gold hoop earrings and clear heels for a sexy summer look.

Fit & Features
- Sleeveless V-neckline
- Thin shoulder straps
- Backless design
- Short, form-hugging fit
- Metallic sweater knit fabric, front center seam detailing
- Runs true to size
Style Number/Barcode: 06005-0665

Category Name: Vacation Looks

Price: $4.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish And Lovely Eyelet Mini Dress
Keep it stylish and lovely with a mini dress that brings sweet details! The dress features a sleeveless square neckline with a mini tie front, adjustable spaghetti straps, an eyelet pattern, and a mini-length silhouette. Complete look with wedges.

Fit & Features
- Sleeveless square neckline
- Mini tie-front
- Adjustable spaghetti straps
- Eyelet pattern
- Mini length silhouette
- Form hugging fit runs true to size
Style Number/Barcode: 05102-1276

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Destined For Sun Chiffon Kimono
Layer this chiffon kimono over your swimsuit or outfit for an elevated allure on vacay or at a chic pool party!

Fit & Features
- Sheer chiffon fabric
- Relaxed short sleeves
- Open front design with tie-front
- Relaxed flowy hem
- Runs true to size
Style Number/Barcode: 06204-000018

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Drawn In With Glam Ruched Mini Dress
Get drawn in with glam in a cute mini dress! The dress features a sleeveless V-neckline, spaghetti straps, a ruched drawstring at the center, and a mini-length silhouette. The dress is composed of a textured knit fabric that offers a form-hugging fit. Complete the look with hoops and mules.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Ruched drawstring at center
- Mini length silhouette
- Textured knit fabric
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-1496

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Charming Florals Ribbed Knit Mini Dress
Bring the charm with a floral mini dress that is perf for your next brunch date! The dress features a sleeveless sweetheart neckline, tie-front, spaghetti straps, ditsy floral print, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit. Complete look with wedges.

Fit & Features
- Sleeveless sweetheart neckline
- Tie-front
- Spaghetti straps
- Ditsy floral print
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4062

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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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