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.

Island Getaway Faux Wrap Mini Skirt
Style up this lightweight mesh mini skirt to look like you're ready for an island getaway! It features a high-rise waist, ruched side seams, a short, curve-hugging fit with a faux wrap-front design at the hem, and an all-over palm leaf print. Style with the matching crop top.

Shop Matching Top: Island Getaway Halter Crop Top

Fit & Features
- High-rise elasticized waist
- Ruched side seams
- Mini-length, form-fitting silhouette, faux wrap-front hem
- Palm leaf print
- Sheer mesh fabric, full knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0598

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Major Mood Square Sunglasses
These oversized square sunglasses bring bold, sleek vibes that say “I’ve arrived”—even if it’s just to iced coffee o’clock.

Fit & Features
- Oversized square frames
- Metal trim
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000078

Category Name: Vacation Looks

Price: $10.90

Availability: Out of Stock
Product Badge:
- Ships Free
She Knows Style Eyelet Lace Skater Dress
Breeze into every occasion in this stylish eyelet lace skater dress! It features a sleeveless square neck, spaghetti straps, a ruched bust, and a flattering fit and flare short-length hem. The sheer eyelet lace fabric includes a full knit lining and offers plenty of stretch. Complete the look with statement block heels for a wedding shower or birthday lunch!

Fit & Features
- Sleeveless square neck, spaghetti straps
- Ruched bust
- Fit and flare, skater silhouette
- Short-length hem
- Sheer eyelet lace fabric, full knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4998

Category Name: Vacation Looks

Price: $19.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
'90s Mood Square Frame Sunglasses
Get in a '90s mood with these trendy sunglasses you've seen all over the gram. They feature a plastic square-shaped frame with tinted lenses. Complete your cool-girl look with large hoop earrings.

Fit & Features
- Plastic square-shaped frame
- Tinted lenses
- 100% UV Protection
Style Number/Barcode: 07008-0985

Category Name: Vacation Looks

Price: $3.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Retro-Chic Ombre Aviator Sunglasses
Accessorize your summer 'fits with these retro-chic sunglasses! They feature an aviator design with a thin metal frame and ombre-tinted lenses. Includes rubber nose pads. Style with a halter crop top and printed flare pants.

Fit & Features
- Aviator design
- Thin metal frame
- Ombre-tinted lenses
- Rubber nose pads
- 100% UV Protection
Style Number/Barcode: 07008-0986

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Beach Mode Chiffon Belted Kimono
Enter into beach mode in this effortlessly chic sheer chiffon kimono perfect for layering over your outfit or swimwear! It features flowy half sleeves, an open front design, a tie-waist belt, side slit accents, and a mid-length hem. Complete the look in trendy denim shorts.

Fit & Features
- Flowy half sleeves
- Open front design
- Tie-waist belt
- Side slit accents
- Mid-length hem
- Sheer chiffon fabric
- Runs true to size
Style Number/Barcode: 06204-1576

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Boho Dreams Printed Cross Waist Flare Pants
Daydream in these boho-printed pants perfect for festivals, concerts, and backyard parties! They feature a flattering cross-high waist, a hip-hugging fit, and a flared hem on stretchy brushed knit fabric. Complete the look in a lace-up crop top.

Fit & Features
- Cross high waist
- Hip-hugging fit
- Flared hem
- Boho print
- Brushed knit stretchy fabric
- Runs true to size
Style Number/Barcode: 06502-2318

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Fun Pleated Micro Mini Skirt
Create trendy fits' with this micro mini skirt for tons of fun under the sun! It features a wide low-rise frayed waist, front pleating, and a frayed mini-length hem on twill denim fabric with a slight stretch. Complete the look in a cute graphic tee and platform sandals!

Fit & Features
- Low-rise wide frayed waist
- Front pleating
- Frayed mini-length hem
- Dual front buttons and hidden zipper closure
- Belt loop accents, two pocket styling
- Twill denim fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06301-0154

Category Name: Vacation Looks

Price: $13.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish Adventure Twill Cargo Joggers
Adventure in style around town in these twill cargo joggers perfect for giving your closet a streetwear vibe! They feature a high-rise elasticized drawstring waist, side pockets, a loose-fit leg silhouette, and lower-side flap pockets, elasticized hem, and are crafted from a woven on-stretch fabric with a cool washed effect. Complete the look with a basic tank top and sneakers.

Fit & Features
- High-rise elasticized drawstring waist
- Side pockets, lower side flap pockets
- Loose-fit leg silhouette
- Elasticized hem
- Woven twill fabric, washed effect, no stretch
- Runs true to size
Style Number/Barcode: 06302-0758

Category Name: Vacation Looks

Price: $6.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay Luxe Rhinestone Espadrille Wedges
Take luxurious steps on vacation in these glitzy espadrille wedges featuring an almond toe, wide rhinestone straps, a platform sole, and a slingback ankle strap with buckle closure. Style with a chic crossbody purse to complete the look!

Fit & Features
- Almond toe
- Wide rhinestone straps
- Platform sole
- Slingback ankle strap, buckle closure
- Espadrille trim
- Runs true to size
Style Number/Barcode: 07406-0331

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Real Style Faux Leather Platform Heels
These faux leather heels have got real style! They feature a square toe, wide toe strap, a thin block heel, a platform, an ankle strap with buckle closure, and a slightly cushioned insole. Complete the look with a trendy crossbody bag for a daytime soiree!

Fit & Features
- Square toe, wide toe strap
- Thin block heel, platform
- Ankle strap with buckle closure
- Slightly cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4406

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Away This Weekend Buckle Platform Wedges
These platform wedges are ready for your weekend away! They feature a square toe, a faux leather strap with studs and a buckle detail, a wooden-like sole, and a wrap-style ankle strap with a buckle closure and stud accents. Complete the look in a wide-leg jumpsuit for a dinner with a view!

Fit & Features
- Square toe
- Faux leather strap, studs, buckle detail
- Wooden-like platform sole
- Wrap-style ankle strap, buckle closure
- Runs true to size
Style Number/Barcode: 07406-0335

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dreamy Looks Mesh V-Neck Babydoll Dress
Showcase a dreamy look in this mesh babydoll dress perfect for date nights or parties! It features a sleeveless V-neckline, adjustable spaghetti straps, ruched bust seams, and a flattering babydoll style silhouette with a mini-length hem. Complete the look in sleek hoop earrings.

Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Ruched bust seams
- Babydoll style silhouette
- Mini-length hem
- Airy mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4971

Category Name: Vacation Looks

Price: $5.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Paint Me In Floral V-Neck Maxi Dress
This floral maxi dress will fit like a dream and give off major artsy vibes! It features a sleeveless V-neckline, spaghetti straps, a hip-hugging fit, and a sultry front slit along the flowy hem. Complete the look in dainty earrings for a daytime soiree!

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Hip-hugging fit
- Front slit, flowy maxi-length hem
- Floral watercolor print
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5018

Category Name: Vacation Looks

Price: $19.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Vacay In Bali One-Shoulder Maxi Dress
Vacation in sultry style wearing this maxi dress! Serve major looks on the island in this dress featuring a sleeveless one-shoulder neckline, a tank strap with a hoop insert, and a form-hugging slim silhouette with a high side slit and ruched seam on textured knit fabric. Complete the look in chic sandals.

Fit & Features
- Sleeveless one-shoulder neckline
- Tank strap, hoop insert
- Form-hugging, slim silhouette
- High side slit, side ruched seam
- Maxi-length hem
- Textured knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4970

Category Name: Vacation Looks

Price: $5.97 $45.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Take Me Away Tube Midi Dress
Effortless but still a serve. This strapless knit midi hugs your curves with a twist-front neckline and scalloped hem—perfect for brunches, beach dates, or packing for your next getaway!

Fit & Features
- Texture knit cotton-blend fabric, moderate stretch
- Sweetheart strapless tube neckline
- Twist bust
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000018

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Modern Marvel One-Shoulder Mini Dress
Strut looking like a modern work of art in this marble-printed mini dress all over town! It features a sleeveless one-shoulder neck, an adjustable spaghetti strap, a side adjustable ruched string, and a bodycon silhouette. Complete the look with hoop earrings.

Fit & Features
- Sleeveless one-shoulder neck
- Adjustable spaghetti straps
- Side ruched string
- Bodycon silhouette
- Mini-length hem
- Marble-printed mesh fabric, stretch knit lining
- Runs true to size
Style Number/Barcode: 05102-4989

Category Name: Vacation Looks

Price: $5.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
What A Sight Eyelet Lace Lace-Up Dress
You'll be quite a dreamy sight in this eyelet lace skater dress! Perfect for wedding showers, grabbing lunch with the girls, or backyard parties. It features adorable puff short sleeves, a sweetheart neck with an underbust seam, an open lace-up back, and a flattering short-length silhouette. Complete the look in strappy block heels.

Fit & Features
- Puff short sleeves
- Sweetheart neck, underbust seam
- Open lace-up back
- Skater silhouette
- Short-length hem
- Eyelet lace cotton fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4946

Category Name: Vacation Looks

Price: $5.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Intentions Floral Tube Top
Show off your sweet side in this adorable tube top! It features a sweetheart neckline with a ruched bust, halter spaghetti straps, a smocked back panel, and a majorly cropped hem. The woven fabric features an all-over ditsy floral print pattern. Style with the matching skater skirt for a brunch-ready look.

Shop Matching Bottoms: Sweet Intentions Floral Skater Skirt

Fit & Features
- Sleeveless sweetheart neckline, ruched bust
- Halter spaghetti straps, tie at the back of the neck
- Smocked back panel
- Cropped fit
- Ditsy floral print
- Woven fabric, front knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1833

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Intentions Floral Skater Skirt
Show off your sweet side in this adorable skater skirt! It features a high-rise smocked waist with an adjustable drawstring, pleated detailing, and a short, fit and flare silhouette. The woven fabric features an all-over ditsy floral print pattern. Style with the matching tube top for a brunch-ready look.

Shop Matching Top: Sweet Intentions Floral Tube Top

Fit & Features
- High-rise smocked waist, elastic waistband
- Adjustable drawstring
- Pleated detailing
- Short hem, fit and flare silhouette
- Ditsy floral print
- Woven fabric, full knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06301-0133

Category Name: Vacation Looks

Price: $12.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Island Guru Pleated Bandeau Top
Elevate your island vacation look with this sassy bandeau crop top perfect for dinner and drinks! It features a sleeveless halter neckline with tie closure and is composed of a pleated satin fabric with lining. Style with the matching bottoms.

Shop Matching Bottoms: Island Guru Pleated Wide Leg Pants

Fit & Features
- Sleeveless halter neckline, tie closure
- Cropped hem
- Pleated satin fabric with lining
- No stretch
- Runs true to size
Style Number/Barcode: 06003-2135

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Island Guru Pleated Wide Leg Pants
Elevate your island vacation look with these sassy satin pants perfect for dinner and drinks! It features a flattering high-rise elasticized smocked waist, and a wide-leg silhouette and is composed of pleated satin fabric with lining. Style with the matching top.

Shop Matching Top: Island Guru Pleated Bandeau Top

Fit & Features
- High-rise elasticized smocked waist
- Wide-leg silhouette
- Pleated satin fabric with lining
- No stretch
- Runs true to size
Style Number/Barcode: 06402-0621

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Running Wild Zebra Print Mini Skirt
Look stylish in this zebra print mini skirt running wild keeping up with your social calendar! It features a high-rise elasticized waist, a bodycon silhouette, and a flirty slit hem on brushed knit stretchy fabric. Complete the look with the matching top.

Shop The Matching Top: Running Wild Zebra Print Crop Top

Fit & Features
- High-rise elasticized waist
- Bodycon silhouette
- Slit mini-length hem
- Zebra print
- Brushed knit stretchy fabric
- Runs true to size
Style Number/Barcode: 06501-0787

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Running Wild Zebra Print Crop Top
Look stylish in this zebra print mini skirt running wild keeping up with your social calendar! It features a sleeveless halter neckline, spaghetti straps, an open lace-up back, and a fitted crop hem on brushed knit stretchy fabric. Complete the look with matching bottoms.

Shop The Matching Bottoms: Running Wild Zebra Print Mini Skirt

Fit & Features
- Sleeveless halter neckline
- Spaghetti straps, lace-up open back
- Fitted crop hem
- Zebra print
- Brushed knit stretchy fabric
- Runs true to size
Style Number/Barcode: 06001-4696

Category Name: Vacation Looks

Price: $3.97 $16.90

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