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.

Totally Fab Tie Dye Midi Dress
Keep it totally fab with a midi dress that channels those pretty vibes! The dress features a sleeveless V-neckline, spaghetti straps, a tie-dye print, and a midi silhouette with a high side slit. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with mules.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Tie-dye print
- Midi silhouette
- High side slit
- Lightweight woven fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-1633

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Take Me Away Tropical Tie-Dye Maxi Dress
Get carried away in this laid-back maxi dress! The dress features a tropical tie-dye print, a sleeveless V-neckline, adjustable spaghetti straps that cross at the back, a smocked waist, and a maxi-length silhouette with a high side slit. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.

Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross at back
- Smocked waist
- Maxi length silhouette, high side slit
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-0576

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Floral Mood Ruched Mini Dress
Channel a floral mood in this romantic mini dress! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a floral print, a ruched drawstring at the side, and a mini-length silhouette. The dress is composed of lined mesh fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and a clutch.

Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Floral print
- Ruched drawstring at the side
- Lined mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1044

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Color Me In Glam Tie Dye Mini Dress
Keep it colorfully glam with a mini dress that is everything! The dress features a sleeveless square neckline, spaghetti straps, a tie-dye hue, a ruched body throughout, and a mini-length silhouette. Complete look with mules and statement cuff.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Tie-dye hue
- Ruched body
- Mini length silhouette
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4077

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Casual-Chic Sweater Knit Dress
Casual and chic, this sweater knit dress is perf for a weekend getaway. It features a sleeveless crew neckline, tank shoulder straps that lead to a cross-back design, and a curve-hugging longline silhouette. Style this dress with a floppy hat and cute sunnies.

Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Cross-back design
- Form-fitting longline silhouette
- Ribbed sweater knit fabric
- Runs true to size
Style Number/Barcode: 06005-1150

Category Name: Vacation Looks

Price: $4.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Step Into Glam Rhinestone Sandals
Step into glamour with these flat sandals. These eye-catching sandals feature two dazzling rhinestone-embellished bands that catch the light with every step.

Fit & Features
- Rhinestone-embellished two bands
- Square toe
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-000033

Category Name: Vacation Looks

Price: $9.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Cross-strap Cheetah Sandals
Keep it chic in sandals that make add a fierce touch to your look! The sandals feature an open back, an open almond toe, cheetah print criss-cross straps, and a nailhead trim. Complete look with a matching top and mini skirt set.

Fit & Features
- Open back
- Open almond toe
- Cheetah print
- Criss-cross straps
- Nailhead trim
- Faux leather footbed
Style Number/Barcode: 07404-0757

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casual Vibes Ribbed Knit Maxi Dress
Achieve those effortless, casual-chic vibes with this ribbed knit maxi dress. It features a sleeveless scoop neckline, spaghetti straps, and a curve-hugging silhouette with a cute side slit to show some leg. Style this dress with sneakers for every day, or heels for date night.

Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Form-hugging fit
- Side slit
- Lined ribbed knit fabric
- Runs true to size
Style Number/Barcode: 05102-4118

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tiki Island Escape Cutout Mini Dress
Create an island escape look with a mini dress that is perf for your next getaway! The dress features a plunging sleeveless v-neckline, halter neck ties, a sexy midriff cut-out, a tropical palm leaf print, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges.

Fit & Features
- Sleeveless V-neckline
- Halter neck ties
- Midriff cutout
- Tropical palm leaf print
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4106

Category Name: Vacation Looks

Price: $13.97 $33.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet And Pretty Butterfly Belly Chain
Get a sweet and pretty look when you accessorize your summer 'fits with this glam belly chain. It features a two-row design with a dainty snake chain and a thicker chain with butterfly charms. Style this accessory with your fave bikini.

Fit & Features
- Two-row design
- Dainty snake chain
- Thick chain, butterfly charms
- Adjustable fit with a lobster clasp closure
Style Number/Barcode: 07002-0855

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sleek And Trendy Belly Chain
Elevate your summertime look with this sleek and trendy belly chain! It features a single-row snake chain design. Style this accessory with your fave flowy maxi skirt to add a subtle hint of glam.

Fit & Features
- Single-row snake chain design
Style Number/Barcode: 07002-0857

Category Name: Vacation Looks

Price: $4.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Classic Destructed Straight-Leg Jeans
These classic destructed straight-leg jeans are perf for a casual everyday look. They feature a high-rise waist, a traditional five-pocket and belt loop design, a front button closure, destructed detailing, and a relaxed straight-leg fit. Style these jeans with a basic tee and sneakers.

Fit & Features
- High-rise waist
- Traditional five-pocket and belt loop design
- Front button closure
- Destructed detailing
- Relaxed straight-leg fit
- Runs true to size
Style Number/Barcode: 06602-0257

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Off To The Tropics Maxi Dress
Head off to the tropics in a maxi dress that instantly puts you in vacay mode! The dress features a sleeveless V-neckline, spaghetti straps that cross at the back, a tropical print, and a maxi silhouette with a high side slit. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps, cross back
- Tropical print
- Maxi length silhouette
- High side slit
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4104

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy In Tie-Dye Satin Mini Dress
Showcase your trendy style this summer season in this adorable satin mini dress. It features a sleeveless cowl neckline, adjustable spaghetti straps that lead to a cross-back design, ruched detailing with side ties, a short, curve-hugging silhouette, and a fab all-over tie-dye print. Complete the look with hoop earrings and clear heels.

Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Cross-back design
- Ruching, side ties
- Mini-length, form-hugging fit
- Satin fabric, tie-dye print, mini skirt length knit lining
- Runs true to size
Style Number/Barcode: 05102-1322

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Pretty Palm Ruched Maxi Dress
Keep it pretty underneath the palm trees in a maxi dress that will have you vacay-ready! The dress features a sleeveless square neckline, adjustable spaghetti straps, a pretty tropical palm leaf print, a high ruched side slit, and a maxi length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals.

Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Tropical palm leaf print
- High ruched side slit
- Maxi length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-0639

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Floral Pop Ruffled Mini Dress
Add a pop of florals to your look with a mini dress that brings the romance! The dress features an off-the-shoulder neckline, a sweetheart bust with ruffled trim, short sleeves, and a ditsy floral print. The dress is composed of a lined mesh fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.

Fit & Features
- Off the shoulder neckline, padded cups
- Sweetheart bust, ruffled trim
- Short sleeves
- Ditsy floral print
- Mini length silhouette
- Lined mesh fabric
- Form hugging, moderate stretch, runs true to size
Style Number/Barcode: 05101-1009

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Essential Oversized Chiffon Kimono
Layer up in a sheer kimono to dress up your casual outfits! The kimono features a draped open front, kimono sleeves, dual side slits, and composed of an airy chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with a bodysuit and cutoff shorts.

Fit & Features
- Draped open front
- Kimono sleeves
- Dual side slits
- Sheer chiffon fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-1001

Category Name: Vacation Looks

Price: $10.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Blooming Beauty Floral Corset Top
Let your beauty bloom with a corset top! The top features a plunging sweetheart neckline, short sleeves, a hook and eye front closure, a lace-up back, and a floral print. Complete look with a mini skirt.

Fit & Features
- Sweetheart neckline, padded cups, undwerwire
- Short sleeves
- Hook and eye front closure
- Lace-up back
- Floral print
- Form hugging fit
- Runs true to size
Style Number/Barcode: 06003-1245

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Level Up Aviators
Take your look to the next level with stylish sunnies! The sunglasses feature a sleek metal trim, nose pads, and an aviator frame. Complete look with an LBD and heels.

Fit & Features
- Metal trim
- Sleek arms
- Nose pads
- Aviator frame
- 100% UV Protection
Style Number/Barcode: 07008-0872

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Always Down Oval Sunglasses
The perfect pair of oval sunglasses to throw on and go on your next adventure or coffee run!

Fit & Features
- Colored frames
- Tinted oval lenses
- 100% UV protection
Style Number/Barcode: 07008-1133

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sleek Stunner Aviators
Keep it sleek and stylish with stunning shades! The sunglasses feature a sleek metal trim, nose pads, and an aviator frame. Complete look with an LBD and heels.

Fit & Features
- Metal trim
- Sleek arms
- Nose pads
- Aviator frame
- 100% UV Protection
Style Number/Barcode: 07008-0871

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Summer Vibes Maxi Dress
This adorable maxi dress brings those trendy summer vibes! It features a sleeveless square neckline, spaghetti straps that lead to a cross-back lace-up design, a high waist seam, and a floor-length fitted silhouette with a thigh-high front slit. The brushed knit fabric has a cool all-over tie-dye print. Style this dress with strappy sandals.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Cross-back lace-up design
- High waist seam
- Floor-length fitted silhouette, front slit
- Brushed knit fabric, moderate stretch, tie-dye print
- Runs true to size
Style Number/Barcode: 05102-4130

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Breezy Boho Vibes Jumpsuit
Get an adorable boho-chic look in this breezy lightweight jumpsuit! It features a sheer lace top with a knit lining, a sleeveless V-neckline, adjustable spaghetti straps, a sheer crochet detailed waist, and flowy woven pant legs. Style this jumpsuit with a floppy hat and strappy sandals.

Fit & Features
- Sheer lace top, knit lining
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Sheer crochet waist
- Flowy woven pant legs
- Runs true to size
Style Number/Barcode: 06302-0237

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Marianna High Slit Floral Dress
Special Occasion

Showcase your passion for florals with a formal dress that is perfect for bridal showers and engagement shoots! Marianna features a sleeveless square neckline, spaghetti straps that cross at the back, a floral print, and a high slit with ruffled trim. Complete look with sandals.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps, cross at back
- Floral print
- High slit, ruffled trim
- Maxi length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05002-1374

Category Name: Vacation Looks

Price: $14.97 $49.90

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